HaCKeRz Kr0nlcKLeZ 1/HaCKeRz Kr0nlcKLeZ.iso/drugs/pihkal.review

Internet Message Format | 1996-05-06 | 96.1 KB

From: [e-mail] (John "John" Berryhill)
Newsgroups: alt.drugs
Subject: PIKHAL by A. Shulgin - A Slothrop Review
Date: 17 Dec 1993 04:36:11 GMT
Message-ID: <2ercvs$[e-mail]>

The following message was sent to me by someone who wishes to remain
known as Tyrone Slothrop.  Tyrone has asked that I post this article
to the appropriate groups.  I no longer have the collected works of
Tyrone Slothrop, although I believe that there are people out there
that have them archived away somewhere.

I am not responsible for the contents of this message.  Indeed, I must
admit that, as of now I have not read it.  If need be, I will arrange
to have reasonable responses delivered to Mr. Slothrop if you send
them to my address.  I don't know whether or when he would be able
to respond since this is the first time I've heard from him in a
couple of years.

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\begin{center}
\Large \bf (Unfinished) Review of PIHKAL:\\
A Chemical Love Story\rm \\
by Alexander Shulgin and Ann Shulgin \normalsize
\end{center}

This document is a response to a careful reading of this fascinating
book by the Shulgins.  It is a long document, and contains five main
sections:

\LP
1) Theology of Sulfur (a scientific response)\\
2) A New Vocabulary (a review of PIHKAL)\\
3) So Many Phenethylamines, So Little Time... (a guide to PIHKAL)\\
4) References\\
5) A Table of 311 Phenethylamines
\eLP

This review is considered to be unfinished, because there is so much
in PIHKAL that it would not be possible to ever finish exploring, and
because this author has other universes to explore as well.
So many universes, so little time...

\newpage

\begin{center}
{\Large {\bf Theology of Sulfur}}\\
{\large {\bf A Scientific Response}}
\end{center}

Some of the richest of the compounds discovered by the Shulgins are
those containing sulfur.  For those of you who want to follow the sulfur
route right over the edge:

\begin{quote}

``Oneirine theophosphate is one way around the problem.  (Tchitcherine:
`You mean thiophosphate, don't you?'  Thinks indicating the presence of
sulfur....  Wimpe: `I mean theophosphate, Vaslav,' indicating the Presence
of God.)....  There is in Laszlo Jamf's celebrated molecule a particular
twist, the so-called `Pokler singularity,' occurring in a certain crippled
indole ring, which later Oneirinists, academician and working professional
alike, are generally agreed is responsible for the hallucinations which are
unique to this drug.  Not only audiovisual, they touch all senses, equally.
And they recur.  Certain themes, `mantic archetypes' (as Jollifox of the
Cambridge School has named them), will find certain individuals again and
again, with a consistency which has been well demonstrated in the
laboratory (see Wobb and Whoaton, `Mantic Archetype Distribution Among
Middle-Class University Students,' J. Oneir. Psy. Pharm., XXIII,
pg. 406-453).  Because analogies with the ghost-life exist, this recurrence
phenomenon is known, in the jargon, as `haunting.'  Whereas other sorts of
hallucinations tend to flow by, related in deep ways that aren't accessible
to the casual dopefiend, these Oneirine hauntings show a definite narrative
continuity, as clearly as, say, the average Reader's Digest article.  Often
they are so ordinary, so conventional - Jeaach calls them `the dullest
hallucinations known to psychopharmacology' - that they are only recognized
as hauntings through some radical though plausible violation of possibility:
the presence of the dead, journeys by the same route and means where one
person will set out later but arrive earlier, a printed diagram which no
amount of light will make readable.  ...On recognizing that he is being
haunted, the subject enters immediately into `phase two,' which, though
varying in intensity from subject to subject, is always disagreeable: often
sedation (0.6 mg atropine subcut.) will be necessary, even though Oneirine
is classified as a CNS depressant.

     ``About the paranoia often noted under the drug, there is nothing
remarkable.  Like other sorts of paranoia, it is nothing less than the
onset, the leading edge, of the discovery that everything is connected,
everything in the Creation, a secondary illumination - not yet blindingly
One, but at least connected, and perhaps a route In for those like
Tchitcherine who are held at the edge....'' Pynchon (1973) Pp. 702-703

\end{quote}

\pagebreak

\begin{abstract}
The recent publication (Shulgin \& Shulgin, 1991) of a large body
of data on human pharmacology of phenethylamines provides an
opportunity for review and interpretation.  This review focuses
on the following two points: 1) Many phenethylamines affect uniquely
human aspects of mental function.  2) Human subjects can distinguish
dozens or perhaps hundreds of phenethylamines.  The interpretation
of these data is that evolution of new human functions of the brain
may have been accompanied by the evolution of a diversity of chemical
communication systems.  Many phenethylamines interact selectively with
these diverse chemical systems, providing a set of tools for selective
study of these functions in the intact human mind.
\end{abstract}

Over the years a growing list of centrally active phenethylamines has
become known, and many of these exert effects in human subjects that
involve uniquely human mental properties, such as the religious or
aesthetic sensibilities.  In spite of the fact that these chemicals
interact with uniquely human aspects of the mind, much of the work on
their pharmacology has been conducted with animals.

None-the-less, there have been active programs of human studies underway,
and a recent publication (Shulgin \& Shulgin, 1991), presented data
from thirty years of research involving hundreds of compounds tested
in humans.  The subject of this 978 page book is the chemistry of the
human mind, and the methodology of its exploration.  The life work of
Alexander Shulgin, summarized in this publication, has led to the
development of a methodology for the exploration of the chemistry of
the human psyche, and he has used that methodology to generate a large
set of chemical tools.

These tools are non-invasive probes of the intact human mind.  Each
individual chemical in this tool set increases the activity of specific
pathways of the brain above their normal background activity level.  This
generates a strong subjective experience of whatever function those specific
brain tissues have in the normal intact mind.  The altered activity is
transient, generally lasting several hours, after which the normal balance
of activity returns.

The book describes 311 chemical compounds, of which 120 were explored to
fully active levels.  Each of these materials has a unique spectrum of
activity, in the sense of which brain tissues it activates.
Phenethylamines are only one of many classes of chemicals which alter
the activity levels of specific brain tissue.  What sets phenethylamine
compounds apart, is that some of the brain pathways whose activity they
alter, affect uniquely human functions, such as cognition, the religious
or aesthetic sentiments, the self-concept, fantasy, childhood memories,
and the unconscious human psyche.

This last observation underscores the significance of Shulgin's
contribution.  The collection of chemical tools he has developed make
possible the dissection of features of the human mind that can not be
explored in animal studies.  The physical structures of the brain,
activated by phenethylamines, which support the unique features of the
human psyche, may have no counterpart in non-human animals.

It is for these reasons that the methodology developed by Shulgin is so
important.  The methodology was first presented in Shulgin, Shulgin and
Jacob (1986) and is revealed again in greater detail in the first half
of Shulgin \& Shulgin (1991).  The method involves careful titration of
one human (Shulgin himself) with each new compound, with special attention
to signs of toxic effects.  This is followed by testing at active levels
by Shulgin and his wife Ann, and then by a research group consisting of
close friends.  Each subject writes a report of the experience after each
experiment.

Shulgin's work is what might be called the natural history of the chemistry
of the mind.  The work is largely descriptive: the determination of which
compounds are active, at what levels, and the characterization of their
subjective qualitative effects (he has also done considerable work in
developing techniques for the synthesis of these compounds).

For most readers of Shulgin \& Shulgin (1991) this natural history will
be all that matters.  The tools can be used by individuals to explore
components of the psyche whose discreteness is normally obscured by
their being embedded in the complete tapestry of the mind.  By
activiting specific components of the mind, they are made to stand out
against the background of the remainder of the psyche, and their
specific contribution to the psychic whole can be better appreciated.
This is a valuable process of self-realization (Shulgin \& Shulgin,
1991, p. 24):

\begin{quote}
...mescaline no more produced beauty than TMA produced anger.  Just as
the beauty was always within me, so was the anger.  Different drugs may
sometimes open different doors in a person, but all of those doors lead
out of the same unconscious.
\end{quote}

However, from the perspective of the neurobiologist, the natural
history of the mind should be only the first phase of the research
program.  The next phase concerns the location and mechanism of
action of these compounds in the human brain.  A great deal is
already known of the mechanisms of action of a few phenethylamines
in animals.  The mechanisms in humans are no doubt essentially the
same, and probably vary only in detail.  The basic mechanism of
action involves inhibition or excitation of some pathways of the brain
as a result of binding and blocking or activating the receptors of
neuro-transmitters such as serotonin or dopamine.

What is most intriguing about the phenethylamines is how subtly
different molecules cause subtly different subjective experiences.
The explanation no doubt lies in the differing spectrums of binding
affinities to and activities at the various receptors in the brain.
Because different receptor types have different physical distributions,
different spectrums of binding affinities and activities will result
in the alteration of activity patterns of different regions of the
brain.  Perhaps the most surprising implication of the phenethylamine
data is that there is evidently a very high diversity of receptor
types for these compounds in humans, thus allowing subtle and
selective pharmacological manipulation of very many specific brain
pathways.

Current research into the action of ``hallucinogens'' is based on
the concept that they could be best understood if we can find a
mechanism of action that is common to all hallucinogens (Titeler,
Lyon, and Glennon, 1988):

\begin{quote}
The phenylisopropylamine hallucinogens produce a syndrome that is
apparently very similar to the spectrum of effects produced by LSD
(Shulgin 1978).  One strategy for uncovering a specific hallucinogenic
site of action for LSD has been to identify a common site of action of
the phenylisopropylamine hallucinogens and LSD.
\end{quote}

While this approach has its value, it is based on a flawed assumption
that these diverse compounds ``produce a very similar syndrome''
(paraphrasing).  Any human who has experienced DOM, DOET, MDA, MDMA and
3,4,5-TMA (this author has not) can testify that these compounds exert
radically different subjective effects.  Yet, clearly there are some
common features of these compounds that cause them to be subjectively
recognized as ``psychedelics'' (this common feature is perhaps the
uniquely human quality of the effects).  Therefore it would not be
surprising if many or most of them shared some common sites and
mechanism of actions (presently, evidence from animal studies indicates
that this commonality is agonism at the 5-HT$_{2}$ receptor).  However,
in humans at least, the commonality is more likely to lie in binding to
a common family of receptors, rather than to a single common receptor.

I would like to suggest that this search for {\it the} mechanism
common to all phenethylamines represents a failure to recognize a
richer and much more interesting phenomenon: the dramatic differences
in subjective effects exhibited by different phenethylamines.  This
failure may be due to the widespread but false belief that they
``produce a very similar syndrome'', a failure arising out of the
paucity of good comparative human pharmacological studies.  While
there may be a receptor site such as 5-HT$_{2}$ that is bound by
many phenethylamines, there must also be many other receptor sites
that are affected differently by different compounds.

I would like to suggest an alternative research program focused on the
diversity of mental effects.  Ideally, we would like to characterize
the physical distribution of every relevant receptor type in the brain,
and then characterize the binding affinity and activity of every active
phenethylamine at every receptor type.  With this information, we could
probe the brain with each phenethylamine, and correlate the subjective
human experience with the physical structures and pathways excited or
inhibited by that compound.  In this way we could map the higher mental
functions altered by phenethylamine to their underlying physical
substrates.

Progress in this direction is obstructed by more than restrictions
on experimentation in human subjects.  The techniques used to
determine the binding affinities and distributions of any class of
chemicals in the brain simply can not be used in humans.  These
studies are always done with animals.  However, animal studies will
not allow us to sort out the interesting details of the diversity of
mental actions of phenethylamines, because the relevant physical
structures and receptor classes may not be present in animal brains.

It has already been suggested that one of the four recognized classes
of serotonin receptors in rat brains, 5-HT$_{1B}$ may not exist in
humans.  Also, it appears that there may be differences in the receptor
currently most implicated in phenethylamine drug action, 5-HT$_{2}$,
between the brains of humans and rats.  Although this receptor bears
the name 5-HT$_{2}$ which implies that it is a receptor for serotonin,
in fact it binds serotonin only weakly, suggesting that it may be a
receptor for an as yet unknown neurotransmitter (Heym \& Jacobs, 1987).

Many receptor molecules have now been studied in detail, and this work
indicates that each receptor class corresponds to a unique protein.
Closely related receptors differ by some amino-acid substitutions in
the receptor protein.  Each receptor class therefore is the product of
a distinct gene within the genome.

The human genome project should ultimately generate a complete catalog
of receptor classes from the human brain.  It will then become possible
to determine if there are receptor classes that are uniquely human.
With the catolog of human receptors and genes available, it should be
possible to manipulate the expression of the receptor genes in tissue
culture, and test the binding affinities of the phenethylamines against
the receptors in vitro.  Once the distribution of these receptors in
the brain is determined, the information would then be in place to
complete the ``ideal'' research program discussed above.

This research program should allow what Shulgin has referred to as
the ``Fourier Transform'' of mental states (Shulgin \& Shulgin, 1991,
p.\ 474-475):

\begin{quote}
``A psychedelic drug experience is a complex combination of many
signals going all at the same time.  Something like the sound of
an oboe playing the notes of the A-major scale.  ...during the
sounding of the note ``A,'' for example, there is a complex
combination of harmonics being produced at the same time... This
mixture defines the played instrument as being an oboe.

This analogy applies precisely to the study of psychedelic drugs
and their actions.... there are many components of a drug's action,
like the harmonics from the fundamental to the inaudible which,
taken in concert, defines the drug.  With muscial instruments, these
components can be shown as sine waves on an oscilloscope....  But in
psychopharmacology?  There is no psychic oscilloscope....  Certainly,
any eventual definition of a drug will require some such dissection
into components each of which makes some contribution to the complex
whole.  The mental process may some day be defined by a particular
combination of these components.''
\end{quote}

This passage indicates that Shulgin considers that each
phenethylamine has a unique spectrum of action, and that we need
a ``psychic oscilloscope'' to characterize them.  What is ironic
is that he does not recognize that the instrument is at hand: the
spectrum of binding affinities and actions at distinct receptor
sites.  This is the instrument he seeks.  In this view, the purest
psychic signal that could be induced chemically, consisting of a
single ``harmonic,'' would be produced by a chemical that bound
exclusively to a single class of receptor.  The finest chemical
dissection of the psyche possible, involves interaction with a
single receptor class.

Throughout Shulgin \& Shulgin (1991) there is repeated discussion of
structure activity relationships and their possible mechanisms
(pp. 53-54, 68-69, 83, 585, 595, 615, 636, 644-646, 680, 691, 696-697,
708, 711, 839-840, 909).  These discussions strike me as being
completely off-base and fruitless.  I believe that the failure of
these musings derives from what could be described as an
``old-fashioned chemist mentality''.

Most of this discussion reveals an unstated assumption that the mental
activity is not the product of the activity of the compound itself,
but of one of its metabolites, or perhaps even the process of
metabolism itself.  The concept that the effect is due to a metabolite
rather than the compound itself reminds me of the panspermia
hypothesis for the origin of life: that life did not originate on
Earth, but came here through space from some other planet.  This does
not tell us how life originated, but simply moves the problem elsewhere.

To assume that the compound itself is active is not only more
parsimonious, but is supported by a large body of evidence from
animal studies.  These studies indicate that phenethylamines bind
with high affinity to specific receptors in the brain, and that
they sometimes activate the receptor, and sometimes block the
receptor (depending on which receptor and which compound).

Apart from the tendency to assign activity to a metabolite rather than
the primary compound, Shulgin reveals little of his personal views on
structure activity relationships in Shulgin \& Shulgin (1991).  However,
in Shulgin (1983) he ventures his favorite speculation:

\begin{quote}
The hows and whys of the action of this fascinating family of compounds is
still a mystery, but some unorthodox speculations are tempting.  Our
cultural heritage requires the initial conclusion that these transient yet
potentially enduring changes of states of consciousness are unnatural or
abnormal.  But perhaps they reveal the ``normal'' state through some
disinhibition of an evolutionarily imposed safeguard.  Perhaps these
chemicals, by themselves, or through the {\it in vivo} conversion to
some intrinsically appropriate metabolite, may serve a neurotransmitter
role at some synaptic network, restoring certain neurological functions
that have been lost through evolution.  To many people, the states of
awareness that are experienced are not ``abnormal,'' but rather, familiar
territory that had been lost in some primal amnesia.
\end{quote}

The theory being advocated by Shulgin, is that there exist in the brain,
certain inactive structures, that were active in our distant past,
but which were inactivated through evolution.  The idea is that when
they were active, humans were mentally very different animals, very
peaceful and comptemplative, perhaps like Christ and the Buddha.  However,
these mental states were not adaptive in the ``cold cruel world'', and
were therefore eleminated by selection.  Or more specifically, the natural
neurotransmitters that activated these structures were eliminated, but
the networks remained.  Now when we ingest the appropriate chemicals,
they play the role of the extinct transmitters, activating the still
existant networks that generate the ancient mental states.

I find this theory unconvincing, because the supposed ancestral
mental state would never have been selected for by Darwinian evolution
in the first place, as it would never have been adaptive in the
``cold cruel world''.  Such an evolution would have required that our
ancestors evolved in some kind of benign garden of eden, for which
there is only contrary evidence.  None-the-less, there remains the
possibility that within the wide range of human genetic variation,
there will appear individuals like Christ and the Buddha, whose mental
makeup varies to these maladaptive extremes through chance rather than
selection.  The occasional presence of such individuals in cultures
can have a tremendous impact, even if the vast majority of humanity
is never able to achieve their level of enlightenment.

\LP
{\bf Summary of Structure Activity Relationships:}
\eLP

Below the chemical elements of structure activity relationships are
briefly summarized, based on a survey of the human activity data
presented by Shulgin:

{\bf The ``ethylamine'' side chain:}

\XPNS
a)  The ethylamine side chain can take the following forms: ethylamine
    or isopropylamine, and an OH group may or may not be placed on the
    nitrogen.  Any other structure causes a drop-off in both quantitative
    and qualitative effectiveness.

b)  The isopropylamine chain generally has a higher potency and longer
    duration than the ethylamine chain, however the ethylamine chain is
    generally found to be qualitatively superior and (at least in the case
    of the sulfur analogues) has a more consistent dose-response relationship.

c)  The presence or absence of an OH group on the nitrogen has little effect
    on either quality or potency.
\eXPNS

{\bf The phenyl ring:}

\XPNS
a)  The ring should have alkoxy and/or alkylthio substituents.

b)  The greatest activity is found with two alkoxy-alkylthio substituents.

c)  The two alkoxy-alkylthio substituents provide greatest activity
    if they are in the 2,5 or 2,6 positions.

d)  The alkoxy-alkylthio substituents provide optimal activity if the
    alkyl group is a methyl.  An ethyl group at the 5 position produces
    a potency similar to the methyl analogue, but shows a much longer
    duration (often too long).  An ethyl group at the 2 position shows
    a decrease in potency and quality.

e)  The 4 position should have a substituent other than H, and a very large
    variety of substituents are suitable.  The substituient at this
    position is critical to both the quantitative and qualitative
    properties of the compound.  Electro-negative groups at this position
    may enhance potency.
\eXPNS

\LP
{\bf A Theory of Structure Activity Relationships:}
\eLP

    Below is a discussion of a speculative theory of ``what they do'',
reflecting on the structure activity observations summarized above.
The theory will be based on several assumptions, which are certainly
not embraced by Shulgin.  These assumptions are the following:

\XPNS
a)  The material is active in its original, un-metabolized form.

b)  The potency of a material is proportional to its binding affinity at
    neurotransmitter receptors in the central nervous system (CNS).

c)  The duration of a material is inversely proportional to its rate of
    metabolism.

d)  The qualitative properties of a material depend on which suite of CNS
    receptors the material binds to.
\eXPNS

Consider that the human brain (like other brains) shows very elaborate
physical specialization, in the sense that specific neurons or groups of
neurons perform specialized functions.  This is nicely illustrated
by the mapping of sensory neurons onto the neocortex.  In the
somatosensory cortex, each point on the surface of the skin maps to
a point on the surface of the cortex, and adjacent points on the skin
map to adjacent points on the cortex.  Thus there exist illustrations
of this mapping in which a homunculus is drawn across the cortex.

Similarly, specialized language functions map to specific regions
of the cortex: Broca's area, Wernicke's area, the arcuate fasciculus
and the angular gyrus.  While few have actually been mapped, it is
reasonable to expect that a wide variety of uniquely human functions
have speciaized, localized physical substrates in the brain.

The specialization of regions of the brain can manifest itself in
many ways.  There is evidence that much of the neocortex is uniform
in that locally it has but one kind of circuitry, and the
specializations of function derive from specialization of inputs
and outputs.  In this view, the auditory and visual cortex are
structurally the same but differ primarily in the sensory modality
of their inputs.

However, at a finer scale, specializations of specific neurons may
be revealed by characteristic morphologies, characteristic firing
patters (e.g., bursty or not), or in the chemistry of the transmitters
they release or respond to.  It is the chemical specialization that
will be the focus here.

It is probably safe to say that in terms of gross morphological
features, the human brain shows the greatest level of complexity
and specialization of known brains.  It seems likely that this
observation could generalize to the level of chemical differentiation
as well.  What is being suggested is that the human brain may well
have a more diverse system of chemical communication than the brains
of any other species.  It seems plausible as well, that any chemical
communication systems that are uniquely human, are likely to be
associated with mental functions that are uniquely human.

Chemical differentiation can be expressed in a variety of ways, but
those that are relevant to this discussion are the differentiation
of transmitter substances and receptors.  If we were to visualize all
cells of the brain which utilize a specific receptor or transmitter,
we would see some kind of a functional unit, which conceivably may
have a peculiar topology that would make it otherwise hard to
recognize as an anatomical unit.

For example, these cells could occur together in a clump or tightly
linked network, thereby forming a clearly defined anatomical structure.
Alternatively they could be widely dispersed through the brain so that
a visualization of these cells alone would take the form of an extremely
thin array sparsely permeating the volume of the brain; and conceivably
these cell might make no contacts among themselves, thus not forming a
network on their own.

Regardless of the degree of anatomical cohesion of these chemically
defined structures, it is likely that in many if not most cases, all
cells that utilize a common chemical system represent some kind of
functional unit.  Thus chemistry provides an alternative method of
dissecting functional units in the brain.  Chemical definition can
conceivably reveal functional structures that would be virtually
impossible to recognize through anatomical studies.

Chemical dissection has the rather unique advantage that through
the use of drugs, it is possible to temporarily alter the activity
of a chemical unit in an intact living brain, human or not.  In
addition, the physical structure of these chemical units can be
mapped by the examination of the brains of cadavers.  Thus by the
combination of physical mapping of receptor distribution and the
administration of receptor specific drugs, it is possible to associate
physical chemical units with their functional significance through
observation of the subjective effects of alterations in the activity
of those units.

If it is true that there are chemical systems that are uniquely
human, and that they are associated with uniquely human mental
function, then identification of drugs that interact with those
unique chemical systems would facilitate understanding of those
systems.  It would appear that phenethylamines may be such tools.
A most interesting aspect of these drugs, as revealed through the
work of the Shulgins, is their diversity of action.  It appears
that human subjects can discriminate dozens if not hundreds of
phenethylamine compounds.  Thus these compounds must interact
differentially with a considerable number of underlying chemical
functional units in the human brain.

The diverse tool kit of phenethylamines developed by the Shulgins
can be used to reveal and explore the functional significance of
those various chemical units that they interact with.  The apparent
ability of humans to distinguish qualitative differences between such
a large number of phenethylamines, provides circumstantial evidence
for the existance of a great diversity of chemical communication
systems in the brain.  The apparent lack of ability of rodents to
discriminate these same materials, suggests that some of this apparent
chemical diversification may be uniquely human.

\LP
{\bf Some Further Speculations:}
\eLP

One of the most intriguing aspects of the data presented in Shulgin \&
Shulgin (1991) is the ``magic of the 4-position''.  If we take 2,5 or
2,6 - dimethoxy phenethylamine or phenylisopropylamine, and play with
the 4-position, we get a wide variety of compounds with distinct effects.
One possible explanation of this data would be the following:

The family of receptor sites to which the phenethylamines bind have
evolved from a common ancestral receptor structure.  Some regions of
the binding site have been conserved in this evolution, and others
have varied.  The region of the binding site that has varied the most,
aligns with the 4-position of the phenethylamine during binding.  The
remainder of the receptor binding site has been relatively conserved
in evolution, and makes the best fit to the 2,5 or 2,6 - dimethoxy
phenethylamine or phenylisopropylamine structure.

It has also been noted that alkylthio phenylisopropylamines show a
lot of variability of effects between individuals.  This suggests
that there is genetic variation within the human population for the
specific receptor classes that best bind these compounds.  These are
fairly wild speculations at this point.  But they have the merit that
they can eventually be tested when the catalog of human receptor types
becomes available for study.

I would like to make an additional point here, about the exploration of
qualitative variations.  It can be tempting to pursue compounds that
make one feel good.  These are certainly the ones that are likely to get
the most use.  However, one of the objectives of psychic exploration is
to become more familiar with the components of the psyche, both positive
and negative.  It appears that Shulgin \& Shulgin (1991) have been
fairly unbiased in this respect.  He describes Aleph-1 as producing
``the most delicious blends of inflation, paranoia and selfishness''
(p. 80).  About 2C-E he said (p. 518):

\begin{quote}
Several people have said, about 2C-E, ``I don't think I like it, since
it isn't that much fun.  But I intend to explore it again''.  There is
something here that will reward the experimenter.... let it rest as being
a difficult and worth-while material.  A very much worth-while material.
\end{quote}

Perhaps the most negative compound explored is TMA.  The original
publication on TMA, Shulgin, Bunnell and Sargent (1961) provides this
description:

\begin{quote}
The emotional responses elicited during the period of maximum...
intoxication... were striking in their intensity.  Anger, hostility,
and megalomaniac euphoria dominated the subject's thoughts and
conversation.  Actual acts of hostility were not observed, but it was
felt that, in at least two subjects, provocation would have precipitated
homicidal violence.
\end{quote}

I have already quoted from Shulgin \& Shulgin (1991) (p. 24) where
Shulgin points out that the anger of TMA and the beauty of mescaline
are not products of the drugs, but different aspects of the same
unconscious, opened up by the drugs.

Finally, it is interesting to wonder at the (evolutionary) reasons for
the apparent chemical diversity of the brain.  The number of known
neurotransmitters is in the dozens and growing rapidly.  For each of
the better studied neurotransmitters, there are several known classes
of receptors.  Why does the brain need more than two chemical communication
systems: one excitatory, and one inhibitory (which could be accomplished
with a single transmitter and two receptors)?  And why does the brain need
multiple receptors for each transmitter?

The chemical diversity suggests that patterns of interconnections
alone are not enough to meet the information processing needs of the
brain.  Different chemical systems must have different information
transmission properties.  In addition, there may be means of globally
affecting the activity of whole systems of neurons that use a common
chemical messenger or receptor.

\newpage

\begin{center}
{\Large {\bf A New Vocabulary}}\\
{\large {\bf A Review of PIHKAL}}
\end{center}

\begin{quote}

``Gustav tends to sneer, but Saure [Bummer] really turns out to be an
adept at the difficult art of papyromancy, the ability to prophesy
through contemplating the way people roll reefers - the shape, the
licking pattern, the wrinkles and folds or absence thereof in the
paper.  `You will soon be in love,' sez Saure, `see this line here.'

```It's long, isn't it?  Does that mean - '

```Length is usually intensity.  Not time.'

...```How do you like this shit?' sez Saure.

```Hubsch,' allows Gustav.  `A trifle stahlig, and perhaps the infinitesimal
hint of a Bodengeschmack behind its Korper, which is admittedly suffig.'

```I would rather have said spritzig,' Saure disagrees, if that indeed is
what it is.  `Generally more bukettreich than last year's harvests,
wouldn't you say?'

```Oh, for an Haut Atlas herbage it does have its Art,  Certainly it can
be described as kernig, even - as can often be said of that sauber
quality prevailing in the Oued Nfis region - authentically pikant.'

```Acutally I would tend to suspect an origin somewhere along the southern
slope of Jebel Sarho.' Saure sez - `note the Spiel, rather glatt and
blumig, even the suggestion of a Fulle in its wurzig audacity-'

```No no no, Fulle is overstating it, the El Abid Emerald we had last
month had Fulle.  But this is obviously more zart than that.'

``The truth is they are both so blitzed that neither one knows what he's
talking about...''  Pynchon (1973, p. 442).

\end{quote}

The book PIHKAL (Phenethylamines I Have Known And Loved), A Chemical
Love Story, is unusual in that it combines under one cover, an
auto-biographical novel about a love triangle, and 30 years of scientific
laboratory notes.  The entire package weighs in at a hefty 978 pages, and
is not padded.  The unusual presentation is a reflection of the subject
matter: the chemistry of the human mind and the methodology of its
exploration.

I consider the life work of Alexander (Sasha) Shulgin to represent one of
the most significant scientific contributions of this century.  I say this
because he has perfected a methodology for the exploration of the chemistry
of the human psyche, and he has used that methodology to generate a large
set of chemical tools.  These tools are non-invasive probes of the intact
human mind.

This methodology violates all acceptable scientific procedures, and as
such is at the root of the scientific advance that Shulgin's work
represents.  It is only when imaginative scientific individuals break
free from scientific traditions that they cease to be builders and
become architects.  This is what underlies scientific revolutions.  In
spite of the revolutionary nature of Shulgin's work, it will not incite
a scientific revolution because in 1986 the methodology was prohibited
by legislation at the national level in the United States.
One can only speculate as to what might become of Shulgin's chemical tool
set, if the use of psychedelics in research or therapy with human subjects
should become accepted at some time in the future.

\begin{center}
\large \bf The Love Story \rm \normalsize
\end{center}

PIHKAL is divided roughly in half, into two books.  ``Book I, The Love
Story'', is an autobiographical novel about a love triangle.  In contrast
to Castenada's presentation of fantasy as fact, the Shulgins have chosen
to present fact as fiction, evidently to protect the guilty.  Under
slightly altered names, the book details the paths that lead Sasha and
Ann Shulgin to psychedelic drugs and to each other.

Having followed the work of Alexander Shulgin for over fifteen years,
I was initially disappointed to discover that he had written less than
a third of Book I.  However, as I read the book, I came to realize that
Ann writes with a greater openness and depth of feeling.  This is not to
say that Sasha can not show as much.  In fact his discussion of his
feelings regarding the death of his wife were remarkably open.  However,
we learn more about Sasha's personal life through Ann's voice than his
own.  On the whole, Book I is startling in how much it reveals of the
personal life of the two Shulgins.  Yet it must be remembered that this
is a fictionalized autobiography, so any particular passage may be either
fact or fiction.

Sasha never discusses sex, and his descriptions of drug experiences tend
to be brief, clinical, and second or third person.  Compare his less than
one page description of his first psychedelic experience (mescaline,
p. 16) to her twenty page description of her first experience (peyote,
p. 111).  While this distinction in their writing is generally true,
there are exceptions.  Sasha's description of his first 2C-E (p. 88)
experience is impressive and fairly detailed, though it sounds unpleasant.
On the other hand, in many of Ann's descriptions, the drug experience
itself is in the background; it is just another thing going on in the
story and is not presented in great detail.  These discussions provide
little insight into the unique properties of the compounds involved.

The ideal would be something like Naranjo (1973), which remains the
best comparative study of psychedelics that I have seen.  Naranjo treats
four compounds (MDA, MMDA, harmaline and ibogaine) in detail, clearly
characterizing the qualitative properties of each and differentiating
between them.  However, he devoted an entire book to these four compounds.
In order for the Shulgins to provide equal detail for their hundreds
of compounds, they would have to produce an encyclopedia, rather than
a mere thousand page book.

Apart from providing relatively detailed descriptions of the subjective
effects of a number of drugs whose effects have not previously been
published, Book I provides a very vivid presentation of the methodology
used to explore these materials.  We meet the research group that tests
the materials after Sasha has determined the effective dose range.  They
gather at the Shulgin's home, in a group of six or eight.  Sasha describes
what he knows of the new material and its dose range.  Each person chooses
their dose, and the material is dissolved in water or juice and taken in a
toast.  After the experience, each member of the group must submit a
written description of the experience.

The selection of examples of drug experiences presented could not easily be
construed to represent an attempt at drug advocacy.  The examples include
as many failures and frightening or unpleasant experiences as pleasurable
ones.  It is evident that it has taken considerable courage to personally
test so many new and completely unknown compounds.  The retrospective of
thirty years of such research evidently indicates that no one in the
research group suffered any harm from the experiments.  However that
outcome could not have been known in advance.

Book I describes two experiences in which it was feared that damage
might have been done.  Chapter 36 describes a group experiment in which
one member became essentially catatonic for the duration of the effects
of the drug.  This caused considerable distress among the other members
of the group who feared that the state may have been caused by neurological
damage from this new and essentially unknown compound.  However, as the
effects of the drug wore off, the catatonic individual regained
responsiveness, and reported ``I was in the most amazing place,...
beautiful,...  an extraordinary experience,... truly fantastic''.

Chapter 38 describes a ``spiritual crisis'', which began 24 hours after
Ann took an inactive dose of a new compound.  This crisis, is described
in Book II as ``a complex and psychologically disruptive syndrome... that
lasted for the better part of a week'' (p. 597).  This is perhaps the most
disturbing passage in the book, as it was a highly unusual experience,
very much like being under the influence of a psychedelic drug, but
continuously for a week, and evidently without the direct contribution of
a psychedelic chemical.  The implication is that extensive experimentation
with psychedelics could make one susceptible to this kind of evidently
uncontrolled and unwelcome experience.  Although the term was not used,
this experience could have been called a ``flash-back''.  Not
coincidentally, Chapter 37 discusses the phenomena of flash-backs.

Another interesting aspect of Book I is the elucidation of how Sasha
Shulgin was able to pursue such an unusual career.  He began working with
psychedleics while employed as a chemist at ``Dole'' chemical company.
Eventually the company began to frown on the work, and he chose to leave
the company to become a free-lance chemist-consultant.  He is an
analytical chemist with a federal license to work with all scheduled
drugs.  His consultant work includes serving as a witness in court cases
concering drugs.

In addition to his decision to leave the company and become independent,
he also made a decision not to take his work underground.  He has continued
to publish much of his work over the years in various scientific
publications, now totaling over 160 articles, patents, chapters and books.

\begin{center}
{\large {\bf The Chemical Story}}
\end{center}

``Book II, The Chemical Story'' is the compilation of thirty years of
Alexander Shulgin's lab notes.  It begins with an index listing 179
phenethylamines.  Book II represents a very bold program of chemical
exploration.  The kinds of functional groups and hetero-atoms placed on
the basic psychedelic phenethylamine skeleton, particularly in the
4-position, are very diverse.  The use of halogens, sulfur, triple-bonds,
cyclopropyl groups, nitro groups, and even a selenium atom indicate a
willingness to try just about anything.  While there are many compounds
that suggest a sort of turning over of stones approach, there are also
instances of systematic exploration of structure - activity relationships.

In some cases it is clear that the synthesis got too far ahead of the
testing.  Book II opens with a chemical joke consisting of wild speculation
of structure activity relationships.  However, underlying the joke is the
fact that eight analogs in the wildly speculative logical series were
synthesized or begun before the fallacy of the enterprise was recognized.
There seems to have been some mania for synthesis.  However, that series
was synthesized at the beginning of the work, about thirty years ago when
Shulgin was relatively naieve about structure activity relationships and
inexperienced with psychedelics.

For each of these 179 compounds, there is a separate entry
in Book II, generally consisting of five parts: Synthesis, Dosage,
Duration, Qualitative Comments, and Extensions and Commentary.

\LP
{\bf Synthesis}
\eLP

    Book II contains explicit and detailed descriptions of the synthesis of
each of the phenethylamines discussed in the book.  The recipes are clear
and complete.  They include considerable discussion of how to isolate and
purify the intermediate reaction products and the final product; critical
information often lacking from such recipies.  It should be possible to
synthesize any of the materials discussed in the book from the information
given, however, this would also require an experienced chemist working in
a well equiped lab.  I raise this issue because the book is published as a
non-techinical ``popular'' work (having already sold over ten thousand
copies).  However, the syntheses could not be completed by most readers.

    Some examples of procedures that clearly require a fully equipped lab
follow: A typical synthesis works up the appropriately substituted
nitrostyrene or nitropropene, which is sometimes a long procedure.  This
product is then reduced with lithium aluminum hydride in a diethyl ether
solution under a helium atmosphere.  Intermediate products are often
purified by distillation under a vacuum.  Some reactions generate noxious
gasses such as hydrogen sulfide, hydrogen chloride, or hydrogen cyanide.
In some reactions, special care had to be taken to avoid an explosion risk.
One synthesis reports that an intermediate product detonated spontaneously
after sitting for a few days.

\LP
{\bf Dosage \& Duration}
\eLP

Each of these are one liners, for example:\\
DOSAGE: 4 -- 8 mg\\
DURATION: 8 -- 16 h.

\LP
{\bf Qualitative Comments}
\eLP

This section consists of a series of paragraphs describing the subjective
effects of the compound.  Each paragraph begins with a dosage, and successive
paragraphs generally represent larger dosages, spanning the full effective
dose range of the compound.  The paragraphs are largely gleaned from the
notes contributed by members of the research group.

\LP
{\bf Extensions and Commentary}
\eLP

     This section is where comments are made about the effects of specific
compounds which go beyond simple descriptions of the effects.  The effects
of different compounds are compared, and speculations about structure
activity relationships appear.  Often this sections presents sub-recipes,
including the complete synthesis, dosage, duration and qualitative effects
of additional compounds related to the title compound.

     The extensions and commentary include considerable discussions
of the system used to name the psychedelic compounds, and also introduces
some basic principles of psychedelic chemistry:  There is a discussion
of sulfur - oxygen chemistry on pages 856-857, and a discussion of the
essential oils and related psychedelics on pages 860-864.  All and all,
I found the extensions and commentary to be the most interesting part of
PIHKAL.

\begin{center}
{\large {\bf Critical Points:}}
\end{center}

     While I have great admiration for the accomplishments of the Shulgins
in exploring the chemistry of the mind, reviewing the book brings up two
points which I find irritating:  1)  Exploration of many of the materials
was abandoned at low levels, indicating an emphasis on potency not quality.
2)  The book is permeated with an ``old-fashioned chemist mentality''
towards structure activity relationships, which ignores the understanding
that can be gained from viewing activity as based on an interaction between
the molecules and neurotransmitter receptors in the brain.  The issue of
structure activity relationships is dealt with in the scientific response
above, while the potency not quality issue is dealt with below.

     Just how many phenethylamines are there?  This is an ambiguous and
unanswerable question.  The more relevant question is: how many psychedelic
phenethylamines are there?  This is still not known, but the question that
we can address, is: how many potentially active phenethylamines are known,
and what is their status?  The index on pages 453-457 lists 179
phenethylamines.  However, study of the 179 ``recipes'' reveals that many
of them describe more than one compound.  Generally, under a single recipe,
data will be presented on closely related materials.  A list was made of
all phenethylamines discussed in Book II, for which there was presented at
least either the synthesis, or data on activity in humans, or a separate
recipe (Table 1, at the end of this document).  This exercise turned up
311 compounds.

     Table 1 contains a ``status'' column, in which each of the 311
compounds was classified into one of the following categories:

\XPNS
U)  Untasted: has been synthesized, but not tested in humans.

S)  Sub-threshold: psychedelic activity has not been demonstrated, however,
    the compound has not been tested up to the 200 mg level.  Mescaline is
    considered active at the 200-400 mg level.  Mescaline is a highly rated
    compound, considered among the top five phenethylamines, based on its
    qualitative properties (p. 570).  Yet mescaline is also the least potent
    phenethylamine still considered to be active.  For this reason, in this
    classification, human titrations are not considered complete unless they
    have shown either activity, signs of toxicity, or they have gone up to
    at least the 200 mg level.

T)  Threshold: the compound was tasted only to threshold levels, thus it has
    not been possible to characterize the psychedelic properties.

X)  Toxic: signs of toxicity appear at dosage levels below which psychedelic
    activity appears.

P)  Physical more than mental: the compound is psychedelic, but generates
    unpleasant physical symptoms which are considered to not be adequately
    compensated for by the mental effects.

A)  Active: clearly shows psychedelic activity.

N)  Not active: the compound has been tested up to at least the 200 mg level,
    and no activity has been found.

O)  Other than psychedelic activity: other than psychedelic activity has been
    demonstrated.  These ``other'' activities include such things as:
    anti-depressant, analgesic, anorexic, adrenergic bronchodilator,
    stimulant and antitussive.

I)  Incomplete synthesis: the synthesis is described, but it has not been
    completed, thus the final phenethylamine is not yet available for study.

?)  Status unknown: the compound appears in the book, but there is no
    statement as to the status, it is probably untested.
\eXPNS

     The distinction between categories X and P is subtle and perhaps not
meaningful.  It is based on the wording presented in the description of the
effects.  Sometimes it is explicitly stated that a material is believed to
be toxic, and these compounds are classified as X.  Other descriptions
report a body load that is greater than the mental effects, and these are
classified as P.

     The counts of compounds in each of the categories are summarized in
Table 2 below:

\begin{tabular}{lrl}
     U)  &   71  &   Untasted\\
     S)  &   51  &   Sub-threshold\\
     T)  &   31  &   Threshold\\
     X)  &    2  &   Toxic\\
     P)  &   11  &   Physical more than mental\\
     A)  &  107  &   Active\\
     N)  &   25  &   Not active\\
     O)  &    8  &   Other than psychedelic activity\\
     I)  &    2  &   Incomplete synthesis\\
     ?)  &    3  &   Status unknown\\
\end{tabular}

     It seems a pity that there are a total of 153 compounds in the combined
U, S, and T categories.  The large number of untasted compounds is due in
part to the fact that some of these compounds were developed as potential
brain imaging compounds, and were never intended to be psychedelics, and so
have not been tasted.  However, these account for less than half of the U
category.

     What is the most frustrating is the S category (and to a lesser extent
the T category), where it seems that the tasting efforts were aborted at
sometimes absurdly low levels.  Here we must recognize that Sasha Shulgin
has chosen to test all compounds on himself before exposing other humans to
the materials.  This is a comendable practice, but it leads to the problem
of ``so many phenethylamines, so little time''.

     It appears that there is yet another reason why many compounds were only
titrated to very low levels.  Many compounds were synthesized as variations
on known active compounds.  They were then titrated up to the level at which
the model compound showed activity.  If they were not active at that level,
titration was stopped.  This indicates that in this work, there was a
greater emphasis on potency than on the qualitative properties of the
compounds.  There may be many mescalines or MDMAs (ecstacy) among these
sub-threshold compounds; materials which show marvelous activity at much
higher doses than have been tested.

     It would be interesting to know the dates of synthesis and testing of
these materials.  I suspect that much of the earlier work placed a great
emphasis on potency, while in his later work, he has shown a greater
interest in quality.  For example, the 2C compounds are generally less
potent but qualitatively better than the 3C compounds.  Yet much of the
work on the 2C compounds has evidently been in the last ten years.
Shulgin (1983) describes this changing focus in his own words:

\begin{quote}

Throughout this early work, I was absorbed primarily with how much of a
chemical it took to achieve an effect, rather than with the nature of the
effect achieved.  In my notes the term ``psychedelic effectiveness''
reflected only the potency.  I left to others the task of determining the
qualitative aspects of the effects of these drugs, and their potential
values.  It was around this time that I became aware that I was trying
to answer a complex question with a hopelessly restricted vocabulary....

A modest wealth of discovery in several research environments throughout the
world began uncovering the generality of psychedelic drug structures and,
much more important to the studies that stemmed from this, a wealth of
qualitative distinctions and values which can be found within them.

Here was the start of my quest of caring.  I began the study of these drugs,
not from the viewpoint of classification and simple assignment of potency,
but inquiring into the values of human interaction that can result from
their study in terms of personal development.  I became aware that it was
of little merit merely to observe what a drug does to the human nervous
system, unless one also observes how it permits a person to interact with
others, and especially, how it allows him to acknowledge himself....

Now, the quest is assuming a different character.  There is a need for
integration.  There are literally hundreds of psychedelic ``catalysts''
currently at hand that run the gamut of potencies and qualitative
characteristics.  But now it is becoming apparent to me that these
materials, rather than being simply flowers in an expanding anthology,
could have value beyond their present acceptance as sensory disinhibitors.

\end{quote}

     While it is a great shame that the titration of so many materials was
abandoned simply because they were less potent than the compound they were
considered an analog to, there are good reasons to seek more potent
compounds:

     The ideal psychedelic would have its direct effect only on the
central nervous system, showing no activity in the peripheral nervous
system.  However, in the real world, any random phenethylamine is likely
to have some level of affinity for binding at receptors in the peripheral
nervous system.  Given that some such affinity may be present, the greater
the dose that is put into the system, the more likely that peripheral
effects will manifest themselves.  Therefore the most potent materials
stand the best chance of having nearly pure CNS activity.

     Another reason for seeking potency is that once a number of extremely
potent compounds are known, their structures can be freely varied in search
of qualitative properties.  Variations on the structure of highly potent
compounds are likely to result in a loss of potency, but when you start from
such a height of potency, there is a lot of room to drop.  This makes it
possible to more freely explore qualitative variations, with less chance of
varying into an inactive structure.

\newpage

\begin{center}
{\Large {\bf So Many Phenethylamines,}}\\
{\Large {\bf So Little Time...}}\\
{\large {\bf A Guide to PIHKAL}}
\end{center}

     Those of you who enjoyed PIHKAL are no doubt looking forward to
the publication of TIHKAL (tryptamines I have known and loved), dealing
with the indole based psychedelics.  An interesting twist on the indole
story is the concept of the indole polymer.  These have also been
developed and experimented with, producing some interesting results,
most notoriously Imipolex.  One experimental subject reports:

\begin{quote}

``They took away my clothes and dressed me in an exotic costume of some
black polymer, very tight at the waist, open at the crotch.  It felt
alive on me. `Forget leather, forget satin,' shivered Drohne.  `This
is Imipolex, the material of the future.'  I can't describe its perfume,
or how it felt - the luxury.  The moment it touched them it brought my
nipples up swollen and begging to be bitten.  I wanted to feel it against
my cunt.  Nothing I ever wore, before or since, aroused me quite as much
as Imipolex.  They promised me brassieres, chemises, stockings, gowns of
the same material.  Drohne had strapped on a gigantic Imipolex penis
over his own.  I rubbed my face against it, it was so delicious....
There was an abyss between my feet.  Things, memories, no way to
distinguish them any more, went tumbling downward through my head.  A
torrent.  I was evacuating all these, out into some void ... from my
vertex, curling, bright-colored hallucinations went streaming ... baubles,
amusing lines of dialogue, objects d'art ...  I was letting them all go.
Holding none.  Was this `submission,' then - letting all these go?''
Pynchon (1973, p. 488).

\end{quote}

Because PIHKAL is so large, I would like to assist readers who have less time
to invest by making available some of the fruits of my careful reading, in
the form of a sort of index to things that I found interesting in the book:

Many readers will want to know which of the 311 compounds presented are
the ``best''.  Early in his career, Sasha classified compounds as better
if they were more potent, regardless of their qualitative effects.  Perhaps
he has mellowed with age, or perhaps he has become more honest.  On page
570, he lists what he considers the five top phenethylamines, based on
``their acceptability and their intrinsic richness''.  They are: 2C-T-7,
2C-T-2, 2C-B, mescaline and 2C-E.  Interestingly, all of them are quite
literally phenethylamines.  That is, none of them are phenylisopropylamines.
It is not clear if the list was meant to be restricted to phenethylamines,
or if none of the phenylisopropylamines made it into the list of the top
five.

\LP
{\bf Descriptions of Drug Experiences in Book I}
\eLP

\XPNS
p. 11-13 his first drug experience: morphine

p. 15-17 his first mescaline experience, description in $<$ 1 page,
   actually a distillation, not a moving description, but a strong one.

p. 22-25 TMA: ``mescaline no more produced beauty than TMA produced anger.
   Just as the beauty was always within me, so was the anger.  Different
   drugs may sometimes open different doors in a person, but all of those
   doors lead out of the same unconscious.''

p. 34-39 MMDA: a description of the experience by ``a poet''.  I find the
   description to be ``new age'' and uninformative.

p. 51-52 MEM: a very powerfull account of a signinficant therapeutic effect
   on a woman whom he used it with.

p. 54-56 DOM: completely clinical description of the drug, except for a
   three line quote at the end of the chapter.

p. 69-74 MDMA: the description of therapeutic benefits are convincing but
   detached, 2nd person.

p. 75-79 MDOH-MDA-marijuana combination: Time-Stop.  Fairly detailed but
   clinical description.  He was frightened, sounds unpleasant.

p. 81-87 Aleph-1: his 1st person present tense narative, the written notes
   from the experience.  But they sound rather crazy.  ``the most delicious
   blends of inflation, paranoia and selfishness''.

p. 88-97 2C-E: and death of wife.  This section is written with a great deal
   of honesty.  The  description of 2C-E is impressive and fairly detailed,
   but sounds unpleasant.

p. 92 describes three trips that were utter failures.

p. 111-131 peyote: she describes peyote with much personal intimacy \&
   detail.  20 pages! compared to his 1 page distillation on p. 16-17.

p. 192-203 MDMA: 11 pages, her first person present narrative.  There is a
   lot of talk by him.  We learn more about his marriage than he told us in
   his own voice.

p. 210-217 Aleph-2: she didn't get off, so it not a very exciting
   description.  But this is the first description of the group.

p. 219-222 2C-B: the description is not very intriguing, given that this
   is one of the ``best'' materials.  Shows that one can have sex with it.

p. 224-229 DOM: again, not a remarkable drug description.  The narration is
   more about their experiment with bondage.  It occurs to me that he never
   discussed sex in his own voice, but she does a lot.

p. 233-239 psilocybine: not a phenethylamine, a decent description of the
   experience.

p. 248 MDMA: used to defeat ``Siberian wastelands'', only a mention.

p. 260 Mescaline: a group experiment at high dose.  The narrative left me
   feeling like an outsider to the experience.

p. 283-285 2C-T-2: a fairly shallow description, focused on the sexual

p. 288-296 DOB: some initial stoned thoughts, some sex, some conversation.
   Little real sense of what the drug does.

p. 303-306 MDMA: a rather remarkable experience in which her anger about
   loosing Shura to Ursula was interrupted by a voice telling her that
   Shura would be hurt and would need her.  This proved to be true.

p. 323-329 LSD: some sense of imagery, sex, conversation, but the drug
   still seems to be in the background.

p. 340-344 2C-I: this is one of the better descriptions.  She describes
   an interesting sensation of the city of Aachen, and some interesting
   imagery.  They have sex.

p. 346-357 5-TOM: this was a fairly detailed group experiment, but a shallow
   material.  One group member went catatonic, causing a scare.

p. 393-395 MDMA: rather brief description of the experience.  Provided
   relief from a spiritual crisis.  There was a lucid dream that night.

p. 408 2C-B: very brief description, had sex and talked

p. 411-418 2C-T-7: a really phenomenal and detailed description by a
   third party.

p. 421-427 2C-E: a detailed description of a very unpleasant experience.

p. 428-433 2C-T-4: a very nice and detailed description.

p. 433 2C-B, 2C-T-4 combination, two sentences.
\eXPNS

\LP
{\bf Discussions of Drug Combinations}
\eLP

\XPNS
p. 75-79 MDOH-MDA-marijuana combination: Time-Stop.  Fairly detailed but
   clinical description.  He was frightened, sounds unpleasant.

p. 433 2C-B, 2C-T-4 combination, two sentences.

p. 471 Aleph-6 - LSD - marijuana combination

p. 497 ``pro-drug''

p. 730-733 ``piggy-back'', ``primer'' experiments

p. 753 MDPR - LSD, ``body window''

p. 755 MDMA - LSD ``piggyback''

p. 758 ``tomoso'' effect

p. 767-769 MEM - MDMA

p. 775 Methyl-DMA - MDMA

p. 777-778 Methyl-DOB - Psilocybine

p. 778 potentiation

p. 892 TMPEA - mescaline

p. 909 TOMOSO effect, more metabolic babble

recipe \#20 2C-B - MDMA
\eXPNS

\LP
{\bf Discussions of Structure - Activity Relationships}
\eLP

\XPNS
p. 53-54 discussion of a structure activity experiment in which the data
   support a receptor rather than metabolic hypothesis.

p. 68-69 the quinone $->$ indole hypothesis of activity.

p. 83 RS $->$ HS assumption of metabolism to explain activity.

p. 356-357 assumption of activity through metabolism

p. 474-475 Beth state, ``Fourier Transform'' of mental states

p. 585 north \& south end of receptor

p. 595 assumption of activity related to metabolism

p. 615 DMPEA: and the ``pink spot''

p. 636 discussion of sub-classes of 5HT receptors

p. 644-646 hydroquinone hypothesis

p. 680 assumption that DOM is active through metabolites

p. 691 activity through metabolism

p. 696-697 discussion of receptor subclasses, chemical classes,
   ``what are they'', ``where do they go'', $->$ ``what do they do''

p. 708 a chemical hypothesis of activity through metabolism, this one relates
   to amphetamine psychosis, and is obsolete in the light of Jacob's studies

p. 711 more speculation about activity requiring metabolism

p. 839-840 the fallacy of predicting potency by structure

p. 909 TOMOSO effect, more metabolic babble
\eXPNS

\LP
{\bf Miscellaneous:}
\eLP

\XPNS
p. 55 ``rubby'' teeth defined

p. 60-65 describes his decision to do his work above ground rather than
   underground.

p. 67-68 encounter between Schultes and Naranjo.

p. 361 discussion of flashbacks.

p. 459 1st commentary, crazy fantasy, untasted material

p. 459, 750-751 crazy logic

p. 464 ego inflation \& mania, ch 14

p. 466 high variability of S amphetamines

p. 474-475 Beth state, ``Fourier Transform'' of mental states

p. 479-480 ten classic ladies

p. 486-487 N-methyl not good (Contrary to MDMA) example of suspected toxicity.

p. 490-492 examples of suspected toxicity

p. 494 BOX series, relation to norepinephrine

p. 498 beta-ethanolamines

p. 514 Tweetios

p. 566-567 pseudo ``next 10 years'' of psychedelics

p. 570 5 top phenethylamines: 2C-T-7, 2C-T-2, 2C-B, 2C-E, mescaline

p. 534 ``record breaking'' length x potency

p. 588 most potent phenethylamine

p. 636 discussion of sub-classes of 5HT receptors

p. 649 an hypnogogic compound

p. 664-671 F-2, F, F-22: these were only run up to the 15 mg range.  A pity,
   they might show interesting activity at ten times the dose.

p. 673 HOT compounds N-OH

p. 676 G-4: The compound is listed even though its synthesis is not complete.
   There are other examples of this in the book.

p. 676 ``for a period of time (about 3 years) by which time...''
   Is this a joke?

p. 682 HOT

p. 686-687 the value of a long experience

p. 696 IRIS assayed only to 9 mg level ``since DOM itself would have been
   smashingly active at this level''.  Did he not care about qualitative
   effects at this time?

p. 750-751, 459 crazy logic

p. 752 triple bond in phenethylamine

p. 764 good Twain quote: ``I like science because it gives one such a
   wholesome return of conjecture from such a trifling investment of fact.''

p. 768 why emphasize potency

p. 774 rabbit recta

p. 784 Doonesbury - designer drugs, analog drug act

p. 786 austronauts of inner space

p. 802 killing mice

p. 808-809 MPM, MIPM, MBM, and MAM were only assayed to levels that showed
   them to be less active than MEM.  This did not allow characterization of
   their qualitative properties.  Too much interest here in quantitative.

p. 814 PE is assayed to the 150 mg level.  Why? when other compounds were
   assayed to much lower levels.

p. 822 explanation of specific meaning of dosage above some value

p. 824 spontaneous detonation after standing for a few days (in synthesis).

p. 836-837 non-psychedelic euphoriant

p. 843 here there is a foreward to the synthesis, but not very interesting

p. 856-857 discussion of S, O chemistry

p. 860-864 the essential oils

p. 867-868 deterioration of Science \& Nature

p. 869 another definition of $<$

p. 879 a statement of an intent to base all syntheses on starting from
   commercially available materials.  Then he goes on to express paranoia
   that some of these will become unavailable due to the WOD, so the present
   synthesis is based on a natural product.

p. 896 a lucid explanation of why human titration was abandoned due to
   physical effects.

p. 902 example of synthesis describing alternate route that does not work well.

p. 920 ``what this book is all about'' quality not quantity
\eXPNS

\newpage

\begin{center}
{\Large {\bf References}}
\end{center}

\begin{quote}

``Felipe is kneeling out in the sun, making his noontime devotionals to
the living presence of a certain rock back in the wasteland of La Rioja,
on the eastern slopes of the Andes.  According to an Argentine legend
from the last century, Maria Antonia Correa followed her lover into that
arid land, carrying their newborn child.  Herders found her a week later,
dead.  But the infant had survived, by nursing from her corpse.  Rocks
near the site of the miracle have since been the objects of yearly
pilgrimages.  But Felipe's particular rock embodies also an intellectual
system, for he believes (as do M. F. Beal and others) in a form of
mineral consciousness not too much different from that of plants and
animals, except for the time scale.  Rock's time scale is a lot more
stretched out.  `We're talking frames per century,' Felipe like everybody
else here lately has been using a bit of movie language, `per millennium!'
Colossal.  But Felipe has come to see, as those who are not Sentient
Rocksters seldom do, that history as it's been laid on the world is only
a fraction, an outward-and-visible fraction.  That we must also look to
the untold, to the silence around us, to the passage of the next rock we
notice - to its aeons of history under the long and female persistence of
water and air (who'll be there, once or twice per century, to trip the
shutter?), down to the lowland where your paths, human and mineral, are
most likely to cross....'' Pynchon (1973, p. 612-613).

\end{quote}

\XP

Brown, Robert E.  1968.  The psychedelic guide to preparation of the
     eucharist in a few of its many guises.  Edited by Robert E. Brown \&
     Associates of the Neo American Church League for Spiritual
     Development \& The Ultimate Authority of the Clear Light.

Darth, Chewbacca.  1977.  The whole drug manufacturers catalog.  Prophet
     Press, 1003 Manhattan Beach Boulevard, Manhattan Beach, CA 90266.

Heym, James, and Barry L. Jacobs.  1987.  Serotonergic mechanisms of
     hallucinogenic drug effects.  Monogr. neural Sci., 13: 55--81.

High Times/Level Press.  1973.  Basic drug manufacture.  High Times Press,
     Box 386, Cooper Station, New York, NY 10003; Level Press, Box 4858,
     San Francisco, CA 94101.

Huxley, Aldous.  1954.  The doors of perception, and Heaven and hell.
     Harper Colophon Books, Harper \& Row, New York.  Pp. 185.

Lamb, F. Bruce.  1971.  Wizard of the upper Amazon, the story of
     Manuel Cordova-Rios.  Houghton Mifflin Company, Boston, 205 p.

reissued as:
Lamb, F. Bruce and Manuel Cordova-Rios.  1987.  Wizard of the upper
     Amazon.  North Atlantic, 204 p.  ISBN 0-938190-80-6

Lamb, F. Bruce.  1985.  Rio Tigre and beyond: the Amazon jungle medicine
     of Manuel Cordova.  North Atlantic, 256 p.  ISBN 0-938190-59-8
     (describes the life of Cordova after he escaped from the Indians)

Leary, Timothy, Ralph Metzner, and Richard Alpert.  1964.  The
     psychedelic experience.  University Books, New Hyde Park.  Pp. 159.

Masters, R. E. L., and Jean Houston.  1966.  The varieties of
     psychedelic experience.  Dell Publishing Co., New York.  Pp. 326.

Naranjo, Claudio.  1973.  The healing journey, new approaches to
     consciousness.  Ballantine Books, New York, 234 p.

Nimble, Jack B.  1986.  The construction and operation of clandestine drug
     laboratories.  Loompanics Unlimited, P.O. Box 1197, Port Townsend, WA
     98368.  ISBN 0-915197-40-7.

Pynchon, Thomas.  1973.  Gravity's Rainbow.  The Viking Press, N.Y.  Pp. 760.

Schultes, Richard Evans, and Albert Hofmann.  1980.  The botany and
     chemistry of hallucinogens.  Revised and enlarged second edition.
     Charles C. Thomas Publishers, Bannerstone House, 301-327 East
     Lawrence Ave., Springfield, Illinois.  ISBN 0-398-03863-5.

Shulgin, Alexander T.  1978.  Psychotomimetic drugs: structure-activity
     relationships.  In: L. L. Iversen, S. D. Iversen, and S. H. Snyder [eds.]
     ``Handbook of Psychopharmacology, Vol. 11''.  Plenum Press, New York.
     Pp. 243-333.  (an excellent review)

Shulgin, A. T.  1981.  Hallucinogens.  In: Manfred E. Wolff [ed.], ``Burger's
     Medicinal Chemistry, 4th ed., Part III.''  John Wiley \& Sons, Inc.
     Pp. 1109-1137.  (an excellent review, covers the indoles,
     as well as other groups)

Shulgin, A. T.  1983.  Twenty years on an ever-changing quest.  In: Lester
     Grinspoon, James B. Bakalar [eds.], ``Psychedelic Reflections'',
     Human Sciences Press, Inc., New York.  Pp. 205-212.
     (an excellent review)

Shulgin, A. T., L. A. Shulgin.  1991.  PIHKAL, phenethylamines I have
     known and loved, a chemical love story.  Transform Press, Lafayette,
     CA.  Pp. 978.

Shulgin, A. T., L. A. Shulgin, and P. Jacob.  1986.  A protocol for the
     evaluation of new psychoactive drugs.  Methods and Findings in
     Experimental and Clinical Pharmacology 8(5): 313--320.
     (a real eye opener)

Shulgin, A. T., S. Bunnell, and T. Sargent.  1961.  The psychotomimetic
     properties of 3,4,5-trimethoxyamphetamine.  Nature 189: 10011--1012.

Smith, Michael Valentine.  1973.  Psychedelic chemistry.  Rip Off Press
     (``Serving the Revolution since 1969''), P.O. Box 14158, San Francisco,
     CA  94114.

Smith, Michael Valentine.  1981.  Psychedelic chemistry.  Loompanics
     Unlimited, P.O. Box 1197, Port Townsend, WA 98368.  ISBN 0-915179-10-5.
     M. V. Smith was the main character of ``Stranger in a strange land''
     by Robert A. Heinlein, a novel well worth reading.

Snyder, Solomon H., H. Weingartner, and L. A. Faillace.  1970.
     DOET (2,5-dimethoxy-4-ethylamphetamine) and DOM (STP) (2,5-
     dimethoxy-4-methylamphetamine), new psychotropic agents: their
     effects in man.  In: D. H. Efron [ed.], ``Psychotomimetic Drugs'',
     Raven Press, N. Y.  Pp. 247-264.

Snyder, S. H., H. Weingartner, and L. A. Faillace.  1971.
     DOET (2,5-dimethoxy-4-ethylamphetamine), a new psychotropic drug.
     Archives of General Psychiatry 24: 50-55.

Snyder, S. H., S. Unger, R. Blatchley, and C. F. Barfknecht.  1974.
     Stereospecific actions of DOET (2,5-dimethoxy-4-ethylamphetamine) in man.
     Arch. Gen. Psychiatry 31: 103-106.

Titeler, M., R. A. Lyon, and R. A. Glennon.  1988.  Radioligand binding
     evidence implicates the brain 5-HT$_{2}$ receptor as a site of action
     for LSD and phenylisopropylamine hallucinogens.  Psychopharmacology,
     94: 213--216.

Watts, Alan W.  1962.  The joyous cosmology, adventures in the chemistry
     of consciousness.  Vintage Books, a division of Random House, New York.
     Pp. 100.

Weingartner, H., S. H. Snyder, L. A. Faillace, and H. Markley.  1970.
     Altered free associations: some cognitive effects of DOET (2,5-
     dimethoxy-4-ethylamphetamine).  Behavioral Science 15(4): 297-303.

\eXP

\newpage

\begin{center}
{\Large {\bf A Table of 311 Phenethylamines}}\\
\end{center}

Shulgin crossed the diamond with the pearl and gave birth to all forms of
light:

\begin{quote}

``It is early morning now.  Slothrop's breath is white on the air.
He is just up from a dream.  Part I of a poem, with woodcuts accompanying
the text - a woman is attending a dog show which is also, in some way, a
stud service.  She has brought her Pekingese, a female with a sickeningly
cute name, Mimsy or Goo-Goo or something, here to be serviced.  She is
passing the time in a garden setting, with some other middle-class ladies
like herself, when from some enclosure nearby she hears the sound of
her bitch, coming.  The sound goes on and on for much longer than
seems appropriate, and she suddenly realizes that the sound is her own
voice, this interminable cry of dog-pleasure.  The others, politely, are
pretending not to notice.  She feels shame, but is helpless, driven now by
a need to go out and find other animal species to fuck.  She sucks the
penis of a multicolored mongrel who has tried to mount her in the street.
Out in a barren field near a barbed-wire fence, winter fires across
the clouds, a tall horse compels her to kneel, passively, and kiss his
hooves.  Cats and minks, hyenas and rabbits, fuck her inside automobiles,
lost at night in the forests, out beside a waterhole in the desert.

``As Part II begins, she has discovered she's pregnant.  Her husband, a
dumb, easygoing screen door salesman, makes an agreement with her:
her own promise is never stated, but in return, nine months from now,
he will take her where she wants to go.  So it is that close to the end of
her term he is out on the river, and American river, in a rowboat, hauling
on the oars, carrying her on a journey.  The key color in this section is
violet.

``Part III finds her at the bottom of the river.  She has drowned.  But all
forms of life fill her womb.  `Using her as mermaid' (line 7), they
transport her down through these green river-depths.  `It was down, and
out again./  Old Squalidozzi, ploughman of the deep,/  At the end of his
day's sowing/  Sees her verdigris belly among the weeds' (lines 10-13),
and brings her back up.  He is a classically-bearded Neptune figure with
an old serene face.  From out of her body streams a flood now of different
creatures, octopuses, reindeer, kangaroos, `Who can say all the
life/  That left her womb that day?'  Squalidozzi can only catch a
glimpse of the amazing spill as he bears her back toward the surface.
Above, it is a mild and sunlit green lake or pond, grassy at the banks,
shaded by willows.  Insects whine and hover.  The key color now is
green.  `And there as it broke to sun/  Her corpse found sleep in the
water/  And in the summer depths/  The creatures took their way/  Each
to its proper love/  In the height of afternoon/  As the peaceful river
went....'''  Pynchon (1973, p. 446-447)

\end{quote}

\pagebreak

\begin{verbatim}

    STATUS:

      A  active
      T  only threshold levels were tasted
      S  only sub-threshold levels tasted
      U  untasted
      N  not active
      X  signs of toxicity below active level
      P  physical more than mental
      O  other, non-psychedelic activity
      F  synthesis not finished

Abbreviations:

      A   = amphetamine
      PEA = phenethylamine
      B   = butane
      MDP = methylenedioxyphenyl

Note that dosages listed for T, S and N categories indicate what levels
these compounds have been tested to.


  #  Code     Status Dosage  Compact chemical name
-------------------------------------------------------------------------------
  1 AEM           S   220   alpha-Ethyl-3,4,5-trimethoxy-PEA
  1 APM           U         alpha-Propyl-3,4,5-trimethoxy-PEA
  1 ABM           U         alpha-Butyl-3,4,5-trimethoxy-PEA
  1 AAM           U         alpha-Amyl-3,4,5-trimethoxy-PEA
  2 AL            A  20-35  4-Allyloxy-3,5-dimethoxy-PEA
  3 ALEPH         A  5-10   4-Methylthio-2,5-dimethoxy-A
  4 ALEPH-2       A   4-8   4-Ethylthio-2,5-dimethoxy-A
  5 ALEPH-4       A  7-12   4-Isopropylthio-2,5-dimethoxy-A
  6 ALEPH-6       A   >40   4-Phenylthio-2,5-dimethoxy-A
  7 ALEPH-7       A   4-7   4-Propylthio-2,5-dimethoxy-A
  8 ARIADNE       O  12-32  2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA
  8 ?             U         1-(2,5-dimethoxyphenyl)-2-aminobutane
  8 ?             U         1-(3,4-dimethoxyphenyl)-2-aminobutane
  8 ?             U         1-(2,5-dimethoxy-4-bromophenyl)-2-aminobutane
  8 ?             U         N,N-dimethyl-1-(2,4-dimethoxyphenyl)-2-aminobutane
  8 ?             U         N,N-dimethyl-1-(2,5-dimethoxyphenyl)-2-aminobutane
  8 ?             U         N,N-dimethyl-1-(3,5-dimethoxyphenyl)-2-aminobutane
  8 ?             U         1-(2,5-dimethoxy-4-methylphenyl)-N-hydroxy-2-aminoB
  8 ?             U         1-(2,4,6-trimethoxyphenyl)-2-aminobutane
  8 ?             U         3,6-dimethoxy-2,4-dimethyl-A
  9 ASB           A 200-280 3,4-Diethoxy-5-methoxy-PEA
 10 B             P  >150   4-Butoxy-3,5-dimethoxy-PEA
 11 BEATRICE      P   >30   2,5-Dimethoxy-4,N-dimethyl-A
 11 ?             U         N-Cyclopropyl-2,5-dimethoxy-4-methyl-A
 12 BIS-TOM       X   160   2,5-Bismethylthio-4-methyl-A
 13 2C-BIS-TOM    U         2,5-Bis-(methylthio)-4-methylphenethylamine
 13 BOB           P  10-20  4-Bromo-2,5,beta-trimethoxy-PEA
 14 BOD           A  15-25  2,5,beta-Trimethoxy-4-methyl-PEA
 14 BOED          A  70-75  2,5-Dimethoxy-beta-ethoxy-4-methyl-PEA
 15 BOH           P 80-120  beta-Methoxy-3,4-methylenedioxy-PEA
 16 BOHD          X   50    2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA
 17 BOM           S   200   3,4,5,beta-Tetramethoxy-PEA
 18 4-Br-3,5-DMA  O  4-10   4-Bromo-3,5-dimethoxy-A
 19 2-Br-4,5-MDA  S   350   2-Bromo-4,5-methylenedioxy-A
 20 2C-B          A  12-24  4-Bromo-2,5-dimethoxy-PEA
 20 2CB-2ETO      A  15-50  4-Bromo-2-ethoxy-5-methoxy-PEA
 20 2CB-2,5-DIETO S   50    4-Bromo-2,5-diethoxy-PEA
 20 6-BR-DMPEA    A  60iv   2-Bromo-4,5-dimethoxy-PEA
 20 ?             A  >60iv  N-Methyl-2-bromo-4,5-dimethoxy-PEA
 21 3C-BZ         A 25-200  4-Benzyloxy-3,5-dimethoxy-A
 21 3C-FBZ        S    4    3,5-Dimethoxy-4-(4-fluorobenzyloxy)amphetamine
 22 2C-C          A  20-40  4-Chloro-2,5-dimethoxy-PEA
 22 2C-CN         U         2,5-Dimethoxy-4-cyano-PEA
 22 2C-COOH       U         2,5-Dimethoxy-4-carboxy-PEA
 23 2C-D          A  20-60  4-Methyl-2,5-dimethoxy-PEA
 23 ?             U         4,N-dimethyl-2,5-dimethoxy-PEA
 23 ?             U         4,N,N-trimethyl-2,5-dimethoxy-PEA
 23 2CD-2ETO      A   60    2-Ethoxy-5-methoxy-4-methyl-PEA
 23 2CD-5ETO      A  40-50  5-Ethoxy-2-methoxy-4-methyl-PEA
 23 2CD-2,5-DIETO T   55    2,5-Diethoxy-4-methyl-PEA
 24 2C-E          A  10-25  4-Ethyl-2,5-dimethoxy-PEA
 24 2CE-5ETO      A  10-15  5-Ethoxy-4-ethyl-2-methoxy-PEA
 25 3C-E          A  30-60  4-Ethoxy-3,5-dimethoxy-A
 26 2C-F          S   250   4-Fluoro-2,5-dimethoxy-PEA
 26 DOF           U         4-Fluoro-2,5-dimethoxy-A
 27 2C-G          A  20-35  3,4-Dimethyl-2,5-dimethoxy-PEA
 28 2C-G-3        A  12-24  3,4-Trimethylene-2,5-dimethoxy-PEA
 29 2C-G-4        I         3,4-Tetramethylene-2,5-dimethoxy-PEA
 30 2C-G-5        A  10-16  3,4-Norbornyl-2,5-dimethoxy-PEA
 31 2C-G-N        A  20-40  1,4-Dimethoxynaphthyl-2-ethylamine
 32 2C-H          U         2,5-Dimethoxy-PEA
 33 2C-I          A  14-22  4-Iodo-2,5-dimethoxy-PEA
 33 2CI-2ETO      A  5-50   2-Ethoxy-4-iodo-5-methoxy-PEA
 34 2C-N          A 100-150 4-Nitro-2,5-dimethoxy-PEA
 35 2C-O-4        T   60    4-Isopropoxy-2,5-dimethoxy-PEA
 36 2C-P          A  6-10   4-Propyl-2,5-dimethoxy-PEA
 37 CPM           A  60-80  4-Cyclopropylmethoxy-3,5-dimethoxy-PEA
 38 2C-SE         T  50-70  4-Methylseleno-2,5-dimethoxy-PEA
 39 2C-T          A 60-100  4-Methylthio-2,5-dimethoxy-PEA
 39 2CT-2ETO      T   50    2-Ethoxy-5-methoxy-4-methylthio-PEA
 39 2CT-5ETO      A   30    5-Ethoxy-2-methoxy-4-methylthio-PEA
 40 2C-T-2        A  12-25  4-Ethylthio-2,5-dimethoxy-PEA
 40 2CT2-2ETO     A   50    2-Ethoxy-4-ethylthio-5-methoxy-PEA
 40 2CT2-5ETO     A   20    5-Ethoxy-4-ethylthio-2-methoxy-PEA
 40 2CT2-2,5DIETO A  10-50  2,5-Diethoxy-4-ethylthio-PEA
 41 2C-T-4        A  8-20   4-Isopropylthio-2,5-dimethoxy-PEA
 41 2CT4-2ETO     A  10-25  2-Ethoxy-5-methoxy-4-(i)-propylthio-PEA
 42 pseudo-2C-T-4 T  8-12   4-Isopropylthio-2,6-dimethoxy-PEA
 43 2C-T-7        A  10-30  4-Propylthio-2,5-dimethoxy-PEA
 43 2CT7-2ETO     A   20    2-Ethoxy-5-methoxy-4-(n)-propylthio-PEA
 43 METHYL-2C-T-7 U         2,5-Dimethoxy-4-(n)-propyl-N-methyl-PEA
 44 2C-T-8        A  30-50  4-Cyclopropylmethylthio-2,5-diimethoxy-PEA
 45 2C-T-9        A 60-100  4-(t)-Butylthio-2,5-dimethoxy-PEA
 46 2C-T-13       A  25-40  4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA
 47 2C-T-15       T   30    4-Cyclopropylthio-2,5-dimethoxy-PEA
 48 2C-T-17       A 60-100  4-(s)-Butylthio-2,5-dimethoxy-PEA
 49 2C-T-21       A  8-12   4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA
 50 4-D           A 200-400 4-Trideuteromethyl-3,5-dimethoxy-PEA
 51 beta-D        A 200-400 beta,beta-Dideutero-3,4,5-trimethoxy-PEA
 52 DESOXY        T 40-120  4-Me-3,5-Dimethoxy-PEA
 53 2,4-DMA       T   60    2,4-Dimethoxy-A
 54 2,5-DMA       P 80-160  2,5-Dimethoxy-A
 54 ?             S   150   2,5-Dimethyl-A
 54 ?             O   10    3,4-Dimethyl-A
 54 ?             O 75-150  2-Methyl-A
 54 ?             O 75-150  3-Methyl-A
 54 ?             P 75-150  4-Methyl-A
 54 2,5-DNNA      U         2,5-Dimethoxy-N,N-dimethyl-A
 54 IDNNA         U         4-Iodo-2,5-dimethoxy-N,N-dimethyl-A
 54 FDNNA         U         4-Fluoro-2,5-dimethoxy-N,N-dimethyl-A
 54 2,5-DMNNA     U         2,5,N,N-Tetramethyl-A
 54 ?             U         4-Fluoro-2,5,N,N-tetramethyl-A
 55 3,4-DMA       A  >160   3,4-Dimethoxy-A
 55 2,6-DNNA      U         2,6-Dimethoxy-N,N-dimethyl-A
 55 3,5-DNNA      U         3,5-Dimethoxy-N,N-dimethyl-A
 56 DMCPA         A  15-20  2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine
 56 TMT           S   13    Trans-2-(3,4,5-trimethoxyphenyl)cyclopropylamine
 57 DME           S   115   3,4-Dimethoxy-beta-hydroxy-PEA
 57 BOHH          S   100   3,4-Methylenedioxy-beta-hydroxy-PEA
 58 DMMDA         A  30-75  2,5-Dimethoxy-3,4-methylenedioxy-A
 58 ?             T   80    threo-2-Amino-3-(2,5-dimethoxy-3,4-MDP)butane
 58 ?             S   10    erythro-2-Amino-3-(2,5-dimethoxy-3,4-MDP)butane
 59 DMMDA-2       A   50    2,3-Dimethoxy-4,5-methylenedioxy-A
 60 DMPEA         N  1000   3,4-Dimethoxy-PEA
 60 ?             N   500   N-Acetyl-3,4-dimethoxy-PEA
 61 DOAM          T   10    4-Amyl-2,5-dimethoxy-A
 62 DOB           A   1-3   4-Bromo-2,5-dimethoxy-A
 63 DOBU          T   2.8   4-Butyl-2,5-dimethoxy-A
 63 DOIB          A  10-15  2,5-Dimethoxy-4-(2-methylpropyl)-A
 63 DOSB          A  25-30  2,5-Dimethoxy-4-(1,1-dimethylethyl)-A
 63 DOTB          S   25    2,5-Dimethoxy-4-(1-methylpropyl)-A
 64 DOC           A  1.5-3  4-Chloro-2,5-dimethoxy-A
 64 DOA           U         2,5-dimethoxy-4-amino-A
 64 DOAA          U         2,5-dimethoxy-4-acetamido-A
 65 DOEF          A  2-3.5  4-(2-Fluoroethyl)-2,5-dimethoxy-A
 66 DOET          A   2-6   4-Ethyl-2,5-dimethoxy-A
 67 DOI           A  1.5-3  4-Iodo-2,5-dimethoxy-A
 67 ?             S    4    1-(2,5-dimethoxy-4-iodophenyl)-2-aminobutane
 68 DOM           A  3-10   4-Methyl-2,5-dimethoxy-A
 68 5-DOM         S   20    2,4-Dimethoxy-5-methyl-A
 68 2-DOM         U         4,5-Dimethoxy-2-methyl-A
 69 pseudo-DOM    A  15-25  4-Methyl-2,6-dimethoxy-A
 69 Z-7.1         ?         2,4-Dimethoxy-6-methyl-A
 69 Z-7.2         U         4-Methyl-2,3,6-trimethoxy-A
 70 DON           A  3-4.5  4-Nitro-2,5-dimethoxy-A
 71 DOPR          A  2.5-5  4-Propyl-2,5-dimethoxy-A
 71 hydroxy-DOPR  S   0.2   2,5-Dimethoxy-4-(1-hydroxypropyl)-A
 71 DOIP          T  20-30  2,5-Dimethoxy-4-(i)-propyl-A
 72 E             A  40-60  4-Ethoxy-3,5-dimethoxy-PEA
 73 EEE           U         2,4,5-Triethoxy-A
 74 EEM           U         2,4-Diethoxy-5-methoxy-A
 75 EME           U         2,5-Diethoxy-4-methoxy-A
 76 EMM           S   50    2-Ethoxy-4,5-dimethoxy-A
 77 ETHYL-J       T   90    N,alpha-diethyl-3,4-methylenedioxy-PEA
 78 ETHYL-K       S   40    N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA
 79 F-2           S   15    Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)
 79 F             S   30    Benzofuran-2,3-dihydro-5-methoxy-6-(2-aminopropane)
 80 F-22          S   15    Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)
 81 FLEA          A 100-160 N-Hydroxy-N-methyl-3,4-methylene-A
 82 G-3           A  12-18  3,4-Trimethylene-2,5-dimethoxy-A
 83 G-4           I         3,4-Tetramethylene-2,5-dimethoxy-A
 84 G-5           A  14-20  3,4-Norbornyl-2,5-dimethoxy-A
 85 GANESHA       A  20-32  3,4-Dimethyl-2,5-dimethoxy-A
 86 G-N           S    2    1,4-Dimethoxynaphthyl-2-isopropylamine
 87 HOT-2         A  10-18  2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA
 88 HOT-7         A  15-25  2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA
 89 HOT-17        A 70-120  2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA
 90 IDNNA         S   2.6   2,5-Dimethoxy-N,N-dimethyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-benzyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-benzyl-4-iodo-N-methyl-A
 90 ?             U         2,5-Dimethoxy-N-cyanomethyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-cyclopropylmethyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N,N-diethyl-A
 90 ?             U         2,5-Dimethoxy-N,N-diethyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-(3-dimethylaminopropyl)-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N,N-dimethyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-dodecyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-N-(n)-hexyl-4-iodo-A
 90 ?             U         2,5-Dimethoxy-4-iodo-N-methyl-A
 90 ?             U         2,5-Dimethoxy-4-iodo-N-methyl-N-(i)-propyl-A
 90 ?             U         2,5-Dimethoxy-4-iodo-N-(i)-propyl-A
 91 IM            N   400   2,3,4-Trimethoxy-PEA
 92 IP            A  40-80  3,5-Dimethoxy-4-isopropoxy-PEA
 93 IRIS          S    9    5-Ethoxy-2-methoxy-4-methyl-A
 94 J             A 150-230 alpha-Ethyl-3,4-methylenedioxy-PEA
 95 LOPHOPHINE    S   250   3-Methoxy-4,5-methylenedioxy-PEA
 96 M             A 200-400 3,4,5-Trimethoxy-PEA
 96 ?             N 300-750 N-Acetyl-3,4,5-trimethoxy-PEA
 96 ?             S   25    N-Methyl-3,4,5-trimethoxy-PEA
 96 ?             N   500   N,N-Dimethyl-3,4,5-trimethoxy-PEA
 96 TMPEA         N   750   3,4,5-Trimethoxyphenylacetic acid
 96 ?             N 10-300  2-(3,4,5-Trimethoxyphenoxy)ethylamine
 96 ?             N 10-400  N,N-Dimethyl-2-(3,4,5-trimethoxyphenoxy)ethylamine
 97 4-MA          P  50-80  4-Methoxy-A
 97 2-MA          U         2-Methoxy-A
 97 3-MA          S   50    3-Methoxy-A
 97 Orthoxine     O   200   N-Methyl-2-methoxy-A
 98 MADAM-6       N   280   2,N-Dimethyl-4,5-methylenedioxy-A
 99 MAL           A  40-65  3,5-Dimethoxy-4-methallyloxy-PEA
100 MDA           A 80-160  3,4-Methylenedioxy-A
100 ALPHA         A 10-140  1-Amino-1-(3,4-methylenedioxyphenyl)propane
100 M-ALPHA       A   60    1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
100 GAMMA         T   200   1-Amino-3-(3,4-methylenedioxyphenyl)propane
100 EDA           T   150   3,4-Ethylidenedioxy-A
100 IDA           U         3,4-Isopropylidenedioxy-A
100 ORTHO-MDA     O   50    2,3-Methylenedioxy-A
101 MDAL          S   180   N-Allyl-3,4-methylenedioxy-A
102 MDBU          S   40    N-Butyl-3,4-methylenedioxy-A
103 MDBZ          S   150   N-Benzyl-3,4-methylenedioxy-A
103 MDIB          U         3,4-Methylenedioxy-N-(i)-butyl-A
103 MDTB          U         3,4-Methylenedioxy-N-(t)-butyl-A
103 MDAM          U         3,4-Methylenedioxy-N-amyl-A
103 MDHE          U         3,4-Methylenedioxy-N-(n)-hexyl-A
103 MDOC          U         3,4-Methylenedioxy-N-(n)-octyl-A
103 MDDE          U         3,4-Methylenedioxy-N,N-diethyl-A
103 MDCM          U         3,4-Methylenedioxy-N-cyanomethyl-A
103 MDBA          U         3,4-Methylenedioxy-N-(t)-butylamino-A
104 MDCPM         S   10    N-Cyclopropylmethyl-3,4-methylenedioxy-A
105 MDDM          S   150   N,N-Dimethyl-3,4-methylenedioxy-A
106 MDE           A 100-200 N-Ethyl-3,4-methylenedioxy-A
106 ?             T   500   3,4-methylenedixoy-N-(2,2,2-trifluoroethyl)-A
107 MDHOET        S   50    N-(2-Hydroxyethyl)-3,4-methylenedioxy-A
108 MDIP          T   250   N-Isopropyl-3,4-methylenedioxy-A
109 MDMA          A 80-150  N-Methyl-3,4-methylenedioxy-A
110 MDMC          T 150-250 N-Methyl-3,4-ethylenedioxy-A
111 MDMEO         S   180   N-Methoxy-3,4-methylenedioxy-A
112 MDMEOET       S   180   N-(2-Methoxyethyl)-3,4-methylenedioxy-A
113 MDMP          T   110   alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA
114 MDOH          A 100-160 N-Hydroxy-3,4-methylenedioxy-A
115 MDPEA         N   300   3,4-Methylenedixoy-PEA
115 METHYL-MDPEA  O   30    N-Methyl-3,4-methylenedixoy-PEA
116 MDPH          A 160-240 alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA
117 MDPL          S   150   N-Propargyl-3,4-methylenedioxy-A
118 MDPR          N   200   N-Propyl-3,4-methylenedioxy-A
119 ME            A 200-350 3,4-Dimethoxy-5-ethoxy-PEA
120 MEDA          N   200   3,4-Ethylenedioxy-5-methoxy-A
120 MTDA          S    8    3-Methoxy-4,5-trimethylenedioxy-A
121 MEE           S   4.6   2-Methoxy-4,5-diethoxy-A
122 MEM           A  20-50  2,5-Dimethoxy-4-ethoxy-A
123 MEPEA         A   300   3-Methoxy-4-ethoxy-PEA
124 META-DOB      T 50-100  5-Bromo-2,4-dimethoxy-A
124 ORTHO-DOB     U         2-Bromo-4,5-dimethoxy-A
125 META-DOT      T   35    5-Methylthio-2,4-dimethoxy-A
126 METHYL-DMA    T   250   N-Methyl-2,5-dimethoxy-A
126 METHYL-TMA    T   240   N-Methyl-3,4,5-trimethoxy-A
126 METHYL-TMA-2  S   120   N-Methyl-2,4,5-trimethoxy-A
126 METHYL-TMA-6  S   30    N-Methyl-2,4,6-trimethoxy-A
127 METHYL-DOB    P    8    4-Bromo-2,5-dimethoxy-N-methyl-A
128 METHYL-J      A 180-210 N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA
129 METHYL-K      S   100   N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA
129 K             U         2-Amino-1-(3,4-methylenedioxyphenyl)pentane
129 L             U         2-Amino-1-(3,4-methylenedioxyphenyl)hexane
129 METHYL-L      U         2-Methylamino-1-(3,4-methylenedioxyphenyl)hexane
129 ETHYL-L       U         2-Ethylamino-1-(3,4-methylenedioxyphenyl)hexane
130 METHYL-MA     P   100   N-Methyl-4-methoxy-A
130 4-MNNA        ?         4-Methoxy-N,N-dimethyl-A
130 2-MNNA        ?         2-Methoxy-N,N-dimethyl-A
131 METHYL-MMDA-2 S   70    N-Methyl-2-methoxy-4,5-methylenedioxy-A
131 DMMDMA        U         2,5-Dimethoxy-N-methyl-3,4-methylenedioxy-A
132 MMDA          A 100-250 3-Methoxy-4,5-methylenedioxy-A
133 MMDA-2        A  25-50  2-Methoxy-4,5-methylenedioxy-A
133 2C-2          S   2.6   2-Methoxy-4,5-methylenedioxy-PEA
133 4C-2          U         1-(2-Methoxy-4,5-methylenedioxyphenyl)-2-aminoB
133 EMDA-2        A 135-185 2-Ethoxy-4,5-methylenedioxy-A
134 MMDA-3a       A  20-80  2-Methoxy-3,4-methylenedioxy-A
135 MMDA-3b       T  60-80  4-Methoxy-2,3-methylenedioxy-A
135 MMDA-5        T   30
136 MME           T   40    2,4-Dimethoxy-5-ethoxy-A
137 MP            N   240   3,4-Dimethoxy-5-propoxy-PEA
138 MPM           T   30    2,5-Dimethoxy-4-propoxy-A
138 MIPM          U         2,5-Dimethoxy-4-(i)-propoxy-A
138 MBM           S   12    4-(n)-Butoxy-2,5-dimethoxy-A
138 MAM           S   12    4-(n)-Amyl-2,5-dimethoxy-A
139 ORTHO-DOT     S   25    2-Methylthio-4,5-dimethoxy-A
140 P             A  30-60  3,5-Dimethoxy-4-propoxy-PEA
141 PE            S   150   3,5-Dimethoxy-4-phenethyloxy-PEA
142 PEA           N  1600   PEA
142 MPEA          N   400   4-Methoxy-PEA
142 4-Cl-PEA      N   500   4-Chloro-PEA
143 PROPYNYL      T   80    4-Propynyloxy-3,5-dimethoxy-PEA
144 SB            N   240   3,5-Diethoxy-4-methoxy-PEA
145 TA            T   35    2,3,4,5-Tetramethoxy-A
146 3-TASB        A   160   4-Ethoxy-3-ethylthio-5-methoxy-PEA
147 4-TASB        P 60-100  3-Ethoxy-4-ethylthio-5-methoxy-PEA
148 5-TASB        P 120-160 3,4-Diethoxy-5-methylthio-PEA
149 TB            T 60-120  4-Thiobutoxy-3,5-dimethoxy-PEA
150 3-TE          A  60-80  4-Ethoxy-5-methoxy-3-methylthio-PEA
151 4-TE          A  20-30  3,5-Dimethoxy-4-ethylthio-PEA
152 2-TIM         N   240   2-Methylthio-3,4-dimethoxy-PEA
153 3-TIM         N   240   3-Methylthio-2,4-dimethoxy-PEA
154 4-TIM         S   160   4-Methylthio-2,3-dimethoxy-PEA
155 3-TM          A 60-100  3-Methylthio-4,5-dimethoxy-PEA
156 4-TM          A  20-40  4-Methylthio-3,5-dimethoxy-PEA
157 TMA           A 100-250 3,4,5-Trimethoxy-A
158 TMA-2         A  20-40  2,4,5-Trimethoxy-A
159 TMA-3         S   100   2,3,4-Trimethoxy-A
160 TMA-4         A   80    2,3,5-Trimethoxy-A
161 TMA-5         A   30    2,3,6-Trimethoxy-A
161 2C-TMA-5      U         2,3,6-Trimethoxy-PEA
162 TMA-6         A  25-50  2,4,6-Trimethoxy-A
162 2C-TMA-6      U         2,4,6-Trimethoxy-PEA
163 3-TME         A 60-100  4,5-Dimethoxy-3-ethylthio-PEA
164 4-TME         A 60-100  3-Ethoxy-5-methoxy-4-methylthio-PEA
165 5-TME         N   200   3-Ethoxy-4-methoxy-5-methylthio-PEA
166 2T-MMDA-3a    S   12    2-Methylthio-3,4-methylenedioxy-A
167 4T-MMDA-2     S   25    4,5-Thiomethylenexoy-2-methoxy-A
168 TMPEA         N   300   2,4,5-Trimethoxy-PEA
169 2-TOET        T   65    4-Ethyl-5-methoxy-2-methylthio-A
170 5-TOET        A  12-25  4-Ethyl-2-methoxy-5-methylthio-A
170 2C-5-TOET     U         4-Ethyl-2-methoxy-5-methylthio-PEA
171 2-TOM         A 60-100  5-Methoxy-4-methyl-2-methylthio-A
171 2C-2-TOM      U         5-Methoxy-4-methyl-2-methylthio-PEA
172 5-TOM         A  30-50  2-Methoxy-4-methyl-5-methylthio-A
172 2C-5-TOM      U         2-Methoxy-4-methyl-5-methylthio-PEA
173 TOMSO         A   150   5-Methoxy-4-methyl-5-methylsulfinyl-A
174 TP            A  20-25  4-Propylthio-3,5-dimethoxy-PEA
175 TRIS          N   240   3,4,5-Triethoxy-PEA
176 3-TSB         N   200   3-Ethoxy-5-ethylthio-4-methoxy-PEA
177 4-TSB         N   240   3,5-Diethoxy-4-methylthio-PEA
178 3-T-TRIS      S   160   4,5-Diethoxy-3-ethylthio-PEA
179 4-T-TRIS      N   200   3,5-Diethoxy-4-ethylthio-PEA
\end{verbatim}

\end{document}

%Tyrone Slothrop
--

                                              John Berryhill