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A Structural Tour of PiHKAL

version 1.1/11-Apr-2000 By rkundalini : [email protected], with monkish help.(For information on changes , et cetera, see Changes)

0. Table of Contents

0. Table of Contents

1. Introduction

1.1 PiHKAL and This Document

1.2 Chemistry Primer

2. Tour of the Phenethylamines

2.1 Substances Derived from Mescaline

2.1.1 The TMAs

2.1.2 The 4-Substituted Mescalines

2.1.3 The Escalines

2.1.4 Other Mescaline Derivatives

2.2 The 2,4,5 Phenethylamines

2.2.1 The XXXs

2.2.2 DOM and its 4-Substituted Derivatives

2.2.3 The Classic Ladies and the Gs2.3 Substances Derived from MDA

2.3.1 Simple N-Substituted MDAs

2.3.2 Derivatives of MDMA

2.3.3 MeO-MDAs

2.3.4 Alpha Homologues of MDA

2.3.5 Other MDA Derivatives

2.4 Alternative Groupings and Miscellaneous Compounds

2.4.1 BOXes
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2.4.2 Benzofurans

3.0 Index to the Phenethylamines

Changes

1. Introduction

1.1 PiHKAL and This Document

In 1991, Alexander (Sasha) and Ann Shulgin published what would have to be the greatest s ingle contribution to

pychede lic chemistry, ever. I refer, of course, to PiHKAL, or Phenethylamines I Have Known And Loved. The he fty 978-

page tome is actually two books bound together. Book I, presented in three parts, is a fascinating and intimate look

into the lives Shura and Alice Borodin, two fictional characters who bear more than a pass ing resemblance to Sasha

and Ann Shulgin. Book II is a compilation of syntheses, "trip reports" and notes regarding 179 substances

synthesized, in most cases for the first time, by Sasha Shulgin.

Book II was made available online with the permission of the Shuglins, to faciltate the free spread of this information.

It is currently available at Erowid and at The Lycaeum, which also has all of the structures online. However, it is worthnoting that the Shuglins deserve our support, especially since the U.S. government began persecuting them in 1994.

Buy this book if you can spare the cash (US $18.95), preferably from Mind Books, who also deserve our support.

With such a large inventory of molecules, the naming scheme is necessarily somewhat esoteric. For the casual reader

with no formal chemistry training, such as myself, it is apparent on reading PiKHAL that there is some underlying plan

to the collection of substances Shulgin has synthesized, however the specifics of this are quite e lusive. For this

reason, primarily for my own education, I decided to prepare a kind of "tour" of the substances presented in PiHKAL,

outlining the structural relationships and naming schemes. I thought this could be of value to others so I've written it

up in the form of this document.

For improved readability you may wish to resize the browser until it is just w ide enough to lose its horizontal

scrollbar.

1.2 Chemistry Primer

As I noted above, my level of chemistry knowledge is not great, however I hope it is sufficient for the purposes of this

tour. For those with no chemsitry knowledge, I present he re a quick rundown of what you need to know. Some

people people may wish to skip to the bit where the phenethylamine backbone is introduced, or even skip straight to
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the start of the tour.

First of all, all of the materials in PiHKAL are known as compounds. This means that they are made up of innumerable

tiny components known as molecules, and that said molecules are all identical and are made up of a number of

different atoms. Atoms themselves are made up of a nucleus, which containsprotons and neutrons, and the nucleus is

surrounded by a cloud ofelectrons. Phew, talk about reductionism. For the purposes of chemistry, protons, electrons

and neutrons can be considered to be indivisible. Electrons and protons are attracted to each-other, which is why the

electrons cloud around the nucleus, but they can't get too close or they start being repelled. The esoteric laws of

Quantum mechanics end up dictating that there is a se ries o f allowed energies of electrons in atoms, and that only acertain number of electrons can occupy a given level. This number increases with the energy of the level. The normal

state of an a tom is that all its levels, except perhaps one uppermost layer, are filled, and that the number of

electrons is equal to the number of protons in the nucleus. Atoms are given names according to the number of

protons : one proton is hydrogen, two protons is helium, three is lithium, etc : these are called the elements.

Chemistry, by and large, is about the interactions of atoms, and these interactions usually have something to do with

the electrons in the upper-most occupied energy level. This means that in many situations, different elements may

behave in similar ways in chemical reactions, if they share the same number of electrons, or same number of free

spaces, in their outer shells. The Periodic Table of the Elements provides a graphical representation of this, which we

won't go into too deeply here.

The most important elements in psychdelic chemistry are carbon, hydrogen and nitrogen. In organic molecules the

atoms are joined toge ther with a type of bond known as the covalent bond. In covalent bonding, the atoms more or

less share the electrons of their outer shells in order to fill them completely. Since hydrogen has one electron and one

free space, two hydrogen atoms can bond to form molecular hydrogen, written as H2 (where the subscript "2" means

the molecule has two of these things : this is called an empirical formula). Carbon has four electrons and four empty

slots in its outer level, so it can bind to four hydrogen atoms to form CH4, known as methane. Two carbon atoms

could also share a pa ir of electrons, leaving three free slots in each, which we could fill with three hydrogen atoms

each in a s imilar way to what we did with methane, to form C2H

6, or ethane. Alternatively, we could share two pairs of

electrons, in what is known as a double bond, meaning only two hydrogens are needed for each carbon, to form C2H4,

or ethene : the -ene signifies the presence o f a double bond. Or, we could connect together three carbon atoms with

two single bonds, requiring three hydrogens for each of the two end carbons, and two hydrogens for the middle one:

this is C3H6, orpropane. If we keep adding atoms of single-bonded carbon and hydrogen, we form butane, pentane,

hexane, heptane, octane, and so on. This is called a homologous series. For members of the methane series (the

saturated(all single bonds) aliphatic(in chains) hydrocarbons) above propane, one can find several arrangements

(called isomers) of each collection of atoms : for example, an isomer of pentane could be made with a central carbon,

singly linked to four -CH3 (methyl) groups. This could be called, ambiguous ly, isopentane , or more precisely, 2,2-
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dimethylpropane, that is propane with two methyl groups (-CH3s) attached to the 2nd carbon.

We could go on forever making ever more complex organic molecules: this is the beauty of carbon. Organic chemistry

is like playing with Lego. However, these simple hydrocarbons don't make good drugs, unless you want brain

damage, so let's move on. The next thing you need to know about is the benzene ring. Take a CH and singly bond its

carbon to the carbon of another CH. Then doubly bond this carbon to the carbon of another CH. Then singly bond

that carbon to another CH, doubly bond that carbon to the carbon of another CH, singly bond that carbon to the

carbon of another CH, and doubly bond that carbon to the carbon o f the original CH. That was a mouthful, from now

on we w ill simply draw the molecules, like this:

Here, each line represents a covalent bond, and each vertex represents a carbon atom. To keep things simple,hydrogen atoms are often left out o f pictures of s tructures, since it is easy to work out where they must go. In this

case we know that carbon always wants four bonds, so here each carbon must have one hydrogen hanging off it.

Now, it actually turns out that the benzene ring is so small that allof the e lectrons in the depicted s ingle and double

bonds are in fact shared equally among the carbons, so the benzene ring is often drawn like this:

Now, remember before when named a pentane isomer by viewing it as propane w ith two methyl groups attached?

This kind of thing happens quite a bit in organic chemistry, where we can replace one chunk of molecule (in this case

a -H) with another (in this case -CH3) that has the same bonding requirements. The chunks are called functional

groups, and are often referred to as s imply "R", when "R" could be any of several function groups leading to a variety

of different molecules based on a common backbone. As you may have surmised, functional groups have names


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which are often derived from molecules that consist of the functional group plus one or more hydrogens. Hence, -CH 3

is refered to as methyl(often shortened to Me). We could also make use ofethyl(-C2H5, Et),propyl, and so-on. Or,

we could put an oxygen (which wants to have two bonds) between the group and whatever it is to be tacked on to,

to have hydroxy(-OH), methoxy(-OCH3 or MeO), ethoxy, and so-on. Or we could pull the same trick with a sulfur atom

to make methylthio (-MeS), ethylthio (-EtS) and so-on.

One very imporant functional group is the amine (NH2) group. This is based on ammonia, (NH3), and is a feature of

the vast majority of psychoactive substances. If we were to take a benzene ring, use it as a functional group (calledphenyl) to tack on to an ethyl group, and tack on an amine on the other end of the ethyl, we would have beta-

phenethylamine, like so:

This molecule is the basis of all of the substances described in book II of PiHKAL. In order to talk about modifications

to the molecule, it is useful to have a way of referring to each carbon atom. Starting with the benzene ring at the s ite

of the bond to the ethyl, we number this "1", and travelling in either direction, number the rest 2, 3, 4, 5, 6. Note that

one could just as eas ily have looked at the structure from the other side (imagine yourself inside the computer

monitor or behind the page) : this is why the 2-position could also be called the 6-position, as long as what was the

3-position was referred to as the 5-position. The other two carbons are called (alpha) and (beta), starting from

the right. The most interesting compounds are those with the phenyl attached at the beta position (a la beta-

phenethylamine). Some alpha-phenethylamines are discussed in the MDA entry of PiHKAL.

Phenethylamine itself is not active*, where the fun comes in is in tacking various things on to it. The s implest change

is to tack on a methyl in the -position : this gives us amphetamine:


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Adding or removing an alpha-methyl is a commonly used tactic in structural explorations. Shulgin refers to the alpha-

methylated molecule as the three-carbon or 3C- version (or the "amphetamine analogue"), and naturally, when the

alpha-methyl is not present, the substance is the two-carbon, 2C- or "phenethylamine analogue". Amphetamine is an

interesting substance however it is not a psychede lic.

Another substance worth knowing about is dopamine, since it is a neurotransmitter that is intimately involved (along

with serotonin, a tryptamine) in the action of the phenethylamines, among many other drugs. Dopamine is 3,4-

dihydroxyphenthylamine (the di- means two hydroxys):

Two related endogenous phenethylamines are epinephrine (beta-hydroxy-N-methyldopamine) and norepinephrine

(beta-hydroxydopamine), also known as adrenaline and noradrenaline. The difference between these substances is

the N-methyl group, and this structural relationship serves as the model for a number of structural variations of other

substances as we will see below.

Shulgin employed a wide range of functional groups in his creations and it isn't worth bogging ourselves down with

the structure of each here: you already have the most common ones. You might refer to an organic chemistry

textbook, or perhaps you could even find something at Web-ster's Organic Chemistry Site, if you are interested.

*: An anonymous experimenter reports: "Beta-phenethylamine itself is only active when smoked or snuffed not by

injection nor by mouth. This explains why Shulgin found no activity. Both active methods are painful and possibly sensitise
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or otherwise damage the tissues they expose. The stimulation and euphoria produced are pleasant but mainly cerebral.

Dose >100mg in a softhead gave noticeable euphoria for 30 minutes and some stimulation for two hours. The simplest

synthesis is destructive distillation of phenylalanine with soda lime but the product is a bit messy though cheap."

2. Tour of the Phenethylamines

What follows is a tour of the substances described in PiHKAL. When discussing variations to structures, it will be

convenient to talk as if we are able to just add groups, atoms, even neutrons wherever we like. Of course in real lifethis is not the case and a small change in structure w ill sometimes demand an entirely different synthesis s trategy.

2.1 Substances Derived from Mescaline

Let's start with the grand-daddy of them all, mescaline:

Mescaline is 3,4,5-trimethoxyphenethylamine, and is of course a beautiful psychedelic found, among other things, in

peyote (Lophophora williamsii) and a number of species o f columnar cacti of the genus Trichocereus. Let's have atinker.

2.1.1 The TMAs

The most obvious thing to try is to methylate that alpha carbon, turning the phenethylamine bit into amphetamine.

The result in this case is 3,4,5-trimethoxyamphetamine, or s imply TMA. One could also move those methoxys around

to different positions (there are six possibilities), forming both the phenethylamine (PEA) and amphetamine (A)

versions. The following table summarizes these substances:


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MeO @ -A -PEA

3,4,5 TMA mescaline

2,4,5 TMA-2 TMPEA

2,3,4 TMA-3 IM

2,3,5 TMA-4 untested



The PEA versions ofTMA-4, TMA-5 and TMA-6 have been made but haven't been tasted : see the corresponding TMA-

x entries of PiHKAL.

Shulgin also describes three dimethoxylated TMA analogues: 2,4-DMA, 2,5-DMA, 3,4-DMA, and the beta-hydroxylated

version of3,4-DMA, DME (so named due to its alternative full name, 3,4-dimethoxyphenyl-beta-ethano lamine, which

is grasping at straws if you ask me). The 2C- version of3,4-DMA also has an entry: DMPEA, as does its 4-ethoxy

homologue, MEPEA, and the N-methylated version of2,5-DMA, METHYL-DMA. One s ingly methoxylated ana logue and

its N-methylated version is included: 4-MA and METHYL-MA. Another TMA-related substance in PiHKAL is TA, which is

essentially the superposition ofTMA and TMA-2. The rationale for the naming of this substance eludes me. It is the

tenth o f Shulgin's Ten Essential Amphetamines (see the entry for TMA), so perhaps TA stands for Tenth

Amphetamine??

2.1.2 The 4-Substituted Mescalines

As will be seen later, the 4-position seems to be an important factor in determining the nature and potency of effects

of phenethylamines. Quite a number of 4-substituted mescalines are described in PiHKAL. The following table lists

them according to the 4-substituent:

4-R -PEA -A

MeO mescaline TMA


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trideuteromethoxy 4-D

Me DESOXY

Br 4-Br-3,5-DMA

EtO E

isopropoxy IP

propoxy P

cyclopropylmethoxy CPM

butoxy B

benzyloxy 3C-BZ

phenethyloxy PE

allyloxy AL

methallyloxy MAL

propynyloxy PROPYNYL

methylthio 4-TM

ethylthio 4-TE

butylthio* TB

propylthio TP

* Note: The short index at the start of Book II and the indices available online list this as thiobutoxy.

Starting from the top of the table we have, of course, mescaline. This is followed by 4-D, in which the three hydrogen

atoms of the 4-methoxy group are present as the single neutron isotope, deuterium. Next is DESOXY, so-named since

it is mescaline with the oxygen removed from the 4-methoxy. This is followed by a series of increasingly mass ive

hydrocarbon subs tituents, a number of which also have a lkylthio versions included at the end of the table. The 3,4-


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dimethoxy-5-alkoxy versions ofE and P are a lso included in PiHKAL, as ME and MP -- the "M" s tands for "meta".

Shulgin notes in the entry for PE, and it is worth repeating here, that 3C-BZ (and its untasted phenethylamine

version, BZ) has nothing to do with the agent of chemical warfare also known as BZ (thankfully).

2.1.3 The Escalines

We have already seen escaline (E -- unlike the the common usage of the term, which is short for Ecstacy, which is

supposedly MDMA) in the above section. A number of analogues are possible by replacing combinations of the 3,4,5-methoxys w ith an ethoxy. These are summarized in the following table. The s trange naming ofSB refers to the fact

that it is 3,5-bisescaline and that the ethoxys are symmetrically placed on the ring. ASB is the asymmetric version; it

is this PiHKAL entry in which Shulgin describes the naming. In chemical nomenclature the "s" in "bis" means, to

paraphrase from Shulgin in the ASB entry, that there are two somethings (ethoxys) attached to something

(phenethylamine), rather than three whatevers (biescaline, two escalines). Likewise, TRIS is

3,4,5-triethoxyphenethylamine, or 3,4,5-trisescaline.

Analogues of these have also been made by replacing one or more oxygen (as part of a methoxy or ethoxy) with a

sulfur atom. The following table lists the relevant substances to be found in PiHKAL:

EtO @ -A 3-EtS-A 4-EtS-A 5-EtS-A

4 E 3-TE 4-TE N/A

3 ME* 3-TME 4-TME 5-TME

3,5 SB 3-TSB 4-TSB

3,4 ASB 3-TASB 4-TASB 5-TASB

3,4,5 TRIS 3-TRIS 4-TRIS

* PiHKAL lists metaescaline (ME) as 5-ethoxy-3,4-methoxyphenethylamine, however the sulfur analogues are listed

with the ethylthio or ethoxy in the 3-position. It is only a matter of naming, anyway.

The 3C- version ofE is given a separate entry in PiHKAL, as 3C-E.

2.1.4 Other Mescaline Derivatives


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TMA proved about twice as potent as mescaline. Shulgin reasoned that pe rhaps even longer carbon side-chains at

the alpha position would further increase potency. The result, alpha-ethylmescaline (AEM), proved inactive at the

hundreds of milligrams level. A number of longer homologues are discussed in the same PiHKAL entry, and are

assumed to be inactive.

The methylthio analogues ofmescaline and IM (isomescaline) have their own entries: 3-TM and 4-TM, and 2-TIM, 3-

TIM and 4-TIM.

Two other derivatives of mescaline are included in PiHKAL: The addition of neutrons to the beta-hydrogens (making

them deuteriums) gives beta-D, and addition of a methoxy at the beta pos ition gives BOM.

2.2 The 2,4,5 Phenethylamines

The exploration of the TMA isomers led to the discovery of the magic of the 2,4,5 configuration. As described above,

the inspiration for this was mescaline, however the family tree of the 2,4,5-s is so rich that it dese rves its own

section.

2.2.1 The XXXs

TMA-2 proved to be positive in effects, at high potency. Shulgin decided to explore modifications of the three methoxy

groups, firstly by forming ethoxy homologues. The naming system of these substances reflects the substitutions: for

example, MEM is 2-methoxy-3-ethoxy-5-methoxyamphetamine (2,5-dimethoxy-4-ethoxy-amphetamine, MEM).

Naturally, there are e ight such structures: MMM (TMA-2), MME, MEM, MEE, EMM, EME, EEM and EEE.

Of these, MEM was the most interesting and the 4-position was chosen as the site of a large range of substitutions,

leading to a large range o f now-famous compounds. The first substitution is the next in the homologous series, 2,5-

dimethoxy-4-propoxyamphetamine (MPM). Shulgin also made versions with isopropoxy, butoxy and amyl groups in

the 4-position : these are described in the PiHKAL entry for MPM. All were abandoned due to reduced potency.

2.2.2 DOM and its 4-Substituted Derivatives

Clearly the 4-position is important to the activity of these substances. To test whether TMA-2 and MEM were

intrinsically active, or whether some metabolite was the active substance, Shulgin replaced the 4-MeO ofTMA-2 with

the more resilient methyl group to form a "DesOxy Methylated" version, DOM : see p. 53 of Book I for the story. DOM,

2,5-dimethoxy-4-methylamphetamine was found to be a very potent psychedelic and forms the prototype for many

structural explorations.


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The following table lists the substances described in PiHKAL that a re derived from DOM by substitution at the 4-

position. Phenethylamine analogues, versions with methylthio rather than methoxy in either the 2- or 5-position, and

beta-substituted PEA versions are also listed.

4-R -A -A, 2-MeS -A, 5-MeS -PEA -R-PEA : name

H 2,5-DMA 2C-H

Me DOM 2-TOM 5-TOM 2C-B MeO : BOD; OH : BOHD

Et DOET 2-TOET 5-TOET 2C-E

propyl DOPR 2C-P

butyl DOBU

amyl DOAM

ethylfluoro DOEF

fluoro DOF; see 2C-F 2C-F

chloro DOC 2C-C

bromo DOB 2C-B MeO : BOB

iodo DOI 2C-I

nitro DON 2C-N

methoxy TMA-2 TMPEA

ethoxy MEM

propoxy MPM

isopropoxy 2C-O-4


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MeSe 2C-SE

MeS ALEPH 2C-T

EtS ALEPH-2 2C-T-2

isopropylthio ALEPH-4 2C-T-4

phenylthio ALEPH-6

propylthio ALEPH-7 2C-T-7

cyclopropylmethylthio 2C-T-8

butylthio 2C-T-9

methoxyethylthio 2C-T-13

cyclopropylthio 2C-T-15

butylthio 2C-T-17

2-fluoroethylthio 2C-T-21

As you can see, a lot of fun has been had working with the 2,4,5 pattern! There are several further derivatives not

included in the table. Versions o f these compounds with the substitution in the 5-position instead of the 4-position

are called the "meta" series. Two such compounds have entries in PiHKAL: META-DOB and META-DOT (DOT is a

synonym ofALEPH). Likewise, ORTHO-DOT is the 2-methylthio version ofTMA-2. The 2,5-bismethylthio (two MeS

groups) version ofDOM is included in PiHKAL as BIS-TOM.

Adding two hydroxys to the amine nitrogen in 2C-T-2, 2C-T-7 and 2C-T-17 gave HOT-2, HOT-7 and HOT-17. The

potency was seemingly unaffected by this substitution, indicating that perhaps the OH is removed metabolically (or

that one is added metabolically to the 2-T series); see the entry for FLEA for an interesting discussion of this.

Placing two methyls on the amine nitrogen o fDOI gave IDNNA. The N-methyl version ofDOB is also included, as

METHYL-DOB. Changing the ethylamine ofDOM to cyclopropylamine yields DMCPA. Building a methylenedioxy ring

across 3,4 gives DMMDA, although this could equally be considered a derivative of MDA.


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As an experiment to investigate an extreme reaction to 5-TOM in "George" (described in chapter 36 of Book I), a

compound called TOMSO was made by putting a methylsulfinyl group in the 5-position ofDOM (or 5-TOM).

Since these compounds were inspired by the 2,4,5-substitued TMA-2, the 2,4,6-substitued TMA-6 which showed

similar promise to TMA-2 ought a lso to act as a model for a family of compounds. Only two of these are described in

PiHKAL : 4-methyl-2,6-dimethoxyampheamine, or pseudo-DOM, and 4-isopropyl-2,6-dimethoxyphenethyamine,

pseudo-2C-T-4. These substances are often written with - as the prefix: this is the greek letter psi, not gamma as

used in the online PiHKAL indices. The entry for pseudo-DOM makes for interesting reading.

2.2.3 The Classic Ladies and the Gs

The alpha-ethyl homologue ofDOM and 2C-B, called ARIADNE is the first of Shulgin's "Classic Ladies" series. This

series, described in the ARIADNE entry, consists of the ten unique homologues of DOM obtained by subsituting

hydrogens (one at a time) with methyls. Not all of these have been synthesized and tried in humans. The Ladies

(with links for those which have been tasted) are: ARIADNE, BEATRICE, CHARMIAN, DAPHNE, ELVIRA, FLORENCE,

GANESHA, HECATE (DOET), IRIS and JUNO. There are suggestions of anti-depressant activity from ARIADNE and a

large number of derivatives of this substance are mentioned her PiHKAL entry.

A number of modifications o fGANESHA are described in PiHKAL. Making a ring with the 3,4 carbons using trimethylene,tetramethylene, or norbornyl gives G-3, G-4, or G-5. One more carbon produces the double-benzene-ringed napthyl

group : the compound is then 1,4-dimethoxynapthyl-2-isopropylamine, or G-N. Phenethylamine analogues of these

are also described : 2C-G-3, 2C-G-4, 2C-G-5 and 2C-G-N (1,4-dimethoxynapthyl-2-ethylamine).

2.3 Substances Derived from MDA

Another psychedelic phenethylamine of importance is MDA. This consists of an amphetamine backbone w ith a

methylenedioxy (-O-CH2-O-) joining the 3,4 phenyl carbons to form a ring:


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A large number of the substances described in PiHKAL are derived from this basic structure. Even after categorizing

them all below, I still find it difficult to go from the names of these substances to their structure : too many Ms and

Ds! It is worth listing them here for reference, anyway.

2.3.1 Simple N-Substituted MDAs

A large proportion of the MDA-derived substances in PiHKAL have one or more substituents on the amine nitrogen

atom. The singly-substituted amphetamines a re as follows:

N-R -A

H MDA

OH MDOH

MeO MDMEO

Me MDMA

Et MDE

2-OH-Et MDHOET

2-MeO-Et MDMEOT

propyl MDPR

isopropyl MDIP

butyl MDBU

benzyl MDBZ

cyclopropylmethyl MDCPM

allyl MDAL

propargyl MDPL


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Only one of the above has its 2C- version listed in PiHKAL: this is MDPEA, the phenethylamine analogue ofMDA. A

number of N-substituted compounds are a lso listed in the next section, and in section 2.3.4.

2.3.2 Derivatives of MDMA

MDMA, of course, is famous for its unique action and has seen extens ive (now underground) use in psychotherapy, as

well as becoming popular among dance enthusiasts and a media favourite "evil designer drug". Shulgin investigated

a number of modifications to the structure in an effort to mediate the undesirable bodily effects ofMDMA (see theentry for FLEA, which also contains other interesting stuff). The doubly N-methylated version ofMDMA is presented as

MDDM. MDMP is the phentermine analogue ofMDMA: this has an extra methyl group attached to the alpha carbon.

Removing the N-methyl from MDMP gives MDPH. The naming gets more esoteric than that, though. Addition of a

methoxy in the 6-position gives MADAM-6, a cheeky name that takes advantage of the nickname ofMDMA, ADAM. The

N-hydroxylated version is called FLEA (as in HADAM/"had 'em")! One wonders if the cook tasted his creations shortly

before naming them. Finally, J (see section 2.3.4) is a fairly close isomer ofMDMA.

2.3.3 MeO-MDAs

A number of substances in PiHKAL are derived from MDA with the addition of one or more methoxy groups. With the

exception ofMDMEO, which is N-methoxy-MDA, all methoxylation takes place on the benzene ring. The follow ing table

lists the amphetamine versions of these. Note that the methoxy position listed refers to a position in MDA; when

named according to the proper rules of nomenclature (e.g. in the PiHKAL Short Index), some substances have their

methylenedioxy at 4,5 instead of 3,4 and hence 2-MeO and 6-MeO are interchanged, and 5-MeO becomes 3-MeO.

MeO @ -A

5 MMDA

6 MMDA-2

2 MMDA-3a

2,5 DMMDA

5,6 DMMDA-2

Several derivatives of these amphetamines are included in PiHKAL LOPHOPHINE (so named due to its expected


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Several derivatives of these amphetamines are included in PiHKAL. LOPHOPHINE (so-named due to its expected

presence in trace quantites in peyote, Lophophora williamsii) is the 2C- version ofMMDA. MEDA is the result of

changing the methylenedioxy ring ofMMDA to an ethylenedioxy. METHYL-MMDA-2 is the N-methylated version of

MMDA-2, whilst 4T-MMDA-2 is its methylenethiooxy analogue. 2T-MMDA-3a is the MeS version ofMMDA-3a. MMDA-3b is

the isomer ofMMDA-3a obtained by switching the 4-position end o f the methylenedioxy group and the 2-methoxy

group, to obtain 4-methoxy-2,3-methylenedioxyamphetamine.

2.3.4 Alpha Homologues of MDA

As an amphetamine, MDA has a methyl group at the alpha position. PiHKAL includes a number of derivatives with

other groups attached to the alpha group. MDMP and MDPH both have an extra methyl at the alpha pos ition, as we

have already seen in section 2.3.2.

The alpha-ethyl and alpha-propyl homologues ofMDA are known as J and K (see METHYL-K) respectively. Their N-

methylated versions are METHYL-J and METHYL-K; the N-ethylated versions are ETHYL-J and ETHYL-K. See the entries

for METHYL-J and J for the bizarre story of the naming of these compounds.

2.3.5 Other MDA Derivatives

A further two compounds in PiHKAL utilise the methylenedioxy ring. 2-Br-4,5-MDA has its structure well-specified by

the name, and is untasted. BOH is beta-methoxy-MDA : see section 2.4.1.

2.4 Alternative Groupings and Miscellaneous Compounds

2.4.1 BOXes

Shulgin lists a number of compounds with a methoxy or hydroxy group attached at the beta position. All of these

have been discussed above as de rivatives ofmescaline (BOM, DME), DOM (BOD, BOHD, BOB) or MDA (BOH : the "H"refers to "homopiperonylamine" [i.e. MDPEA], see the entry for METHYL-J). The idea w ith these substances was to

emulate the relationship between dopamine and norepinephrine (beta-hydroxydopamine): see the entries for BOD,

DME and BOH for discussion.

2.4.2 Benzofurans

As an excuse to attend a marijuana conference in Sweden (see chapter 10 of book I, and the entry for F-2), Shulgin

synthesized two amphetamines w ith (mono and di-) methylated furan rings fused to the benzene ring. These were

supposed to vaguely resemble THC and were called F-2 and F-22


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supposed to vaguely resemble THC, and were called F 2 and F 22.

3.0 Index to the Phenethylamines

The following is a list of a ll the P iKHAL substances. Included are links to the most relevant section of the tour

presented above, and to the PiHKAL entries supplied by Erowid and The Lycaeum. As noted in the introduction, the

Lycaeum has the structural formulae available online.

1 AEM 2.1.4 Erowid Lycaeum a-Ethyl-3,4,5-trimethoxy-PEA

2 AL 2.1.2 Erowid Lycaeum 4-Allyloxy-3,5-dimethoxy-PEA

3 ALEPH 2.2.2 Erowid Lycaeum 4-Methylthio-2,5-dimethoxy-A

4 ALEPH-2 2.2.2 Erowid Lycaeum 4-Ethylthio-2,5-dimethoxy-A

5 ALEPH-4 2.2.2 Erowid Lycaeum 4-Isopropylthio-2,5-dimethoxy-A

6 ALEPH-6 2.2.2 Erowid Lycaeum 4-Phenylthio-2,5-dimethoxy-A

7 ALEPH-7 2.2.2 Erowid Lycaeum 4-Propylthio-2,5-dimethoxy-A

8 ARIADNE 2.2.3 Erowid Lycaeum 2,5-Dimethoxy-a-ethyl-4-methyl-PEA

9 ASB 2.1.3 Erowid Lycaeum 3,4-Diethoxy-5-methoxy-PEA

10 B 2.1.2 Erowid Lycaeum 4-Butoxy-3,5-dimethoxy-PEA

11 BEATRICE 2.2.3 Erowid Lycaeum 2,5-Dimethoxy-4,N-dimethyl-A

12 BIS-TOM 2.2.2 Erowid Lycaeum 2,5-Bismethylthio-4-methyl-A

13 BOB 2.2.2 Erowid Lycaeum 4-Bromo-2,5,beta-trimethoxy-PEA

14 BOD 2.2.2 Erowid Lycaeum 2,5,beta-Trimethoxy-4-methyl-PEA

15 BOH 2.4.1 Erowid Lycaeum beta-Methoxy-3,4-methylenedioxy-PEA

16 BOHD 2 2 2 Erowid Lycaeum 2 5-Dimethoxy-beta-hydroxy-4-methyl-PEA
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16 BOHD 2.2.2 Erowid Lycaeum 2,5 Dimethoxy beta hydroxy 4 methyl PEA

17 BOM 2.1.4 Erowid Lycaeum 3,4,5,beta-Tetramethoxy-PEA

18 4-Br-3,5-DMA 2.1.2 Erowid Lycaeum 4-Bromo-3,5-dimethoxy-A

19 2-Br-4,5-MDA 2.3.5 Erowid Lycaeum 2-Bromo-4,5-methylenedioxy-A

20 2C-B 2.2.2 Erowid Lycaeum 4-Bromo-2,5-dimethoxy-PEA

21 3C-BZ 2.1.2 Erowid Lycaeum 4-Benzyloxy-3,5-dimethoxy-A

22 2C-C 2.2.2 Erowid Lycaeum 4-Chloro-2,5-dimethoxy-PEA

23 2C-D 2.2.2 Erowid Lycaeum 4-Methyl-2,5-dimethoxy-PEA

24 2C-E 2.2.2 Erowid Lycaeum 4-Ethyl-2,5-dimethoxy-PEA

25 3C-E 2.1.3 Erowid Lycaeum 4-Ethoxy-3,5-dimethoxy-A

26 2C-F 2.2.2 Erowid Lycaeum 4-Fluoro-2,5-dimethoxy-PEA

27 2C-G 2.2.3 Erowid Lycaeum 3,4-Dimethyl-2,5-dimethoxy-PEA

28 2C-G-3 2.2.3 Erowid Lycaeum 3,4-Trimethylene-2,5-dimethoxy-PEA

29 2C-G-4 2.2.3 Erowid Lycaeum 3,4-Tetramethylene-2,5-dimethoxy-PEA

30 2C-G-5 2.2.3 Erowid Lycaeum 3,4-Norbornyl-2,5-dimethoxy-PEA

31 2C-G-N 2.2.3 Erowid Lycaeum 1,4-Dimethoxynaphthyl-2-ethylamine

32 2C-H 2.2.2 Erowid Lycaeum 2,5-Dimethoxy-PEA

33 2C-I 2.2.2 Erowid Lycaeum 4-Iodo-2,5-dimethoxy-PEA

34 2C-N 2.2.2 Erowid Lycaeum 4-Nitro-2,5-dimethoxy-PEA

35 2C-O-4 2.2.2 Erowid Lycaeum 4-Isopropoxy-2,5-dimethoxy-PEA

36 2C-P 2.2.2 Erowid Lycaeum 4-Propyl-2,5-dimethoxy-PEA
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36 2C P 2.2.2 Erowid Lycaeum 4 Propyl 2,5 dimethoxy PEA

37 CPM 2.1.2 Erowid Lycaeum 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA

38 2C-SE 2.2.2 Erowid Lycaeum 4-Methylseleno-2,5-dimethoxy-PEA

39 2C-T 2.2.2 Erowid Lycaeum 4-Methylthio-2,5-dimethoxy-PEA

40 2C-T-2 2.2.2 Erowid Lycaeum 4-Ethylthio-2,5-dimethoxy-PEA

41 2C-T-4 2.2.2 Erowid Lycaeum 4-Isopropylthio-2,5-dimethoxy-PEA

42 -2C-T-4 2.2.2 Erowid Lycaeum 4-Isopropylthio-2,6-dimethoxy-PEA

43 2C-T-7 2.2.2 Erowid Lycaeum 4-Propylthio-2,5-dimethoxy-PEA

44 2C-T-8 2.2.2 Erowid Lycaeum 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA

45 2C-T-9 2.2.2 Erowid Lycaeum 4-(t)-Butylthio-2,5-dimethoxy-PEA

46 2C-T-13 2.2.2 Erowid Lycaeum 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA

47 2C-T-15 2.2.2 Erowid Lycaeum 4-Cyclopropylthio-2,5-dimethoxy-PEA

48 2C-T-17 2.2.2 Erowid Lycaeum 4-(s)-Butylthio-2,5-dimethoxy-PEA

49 2C-T-21 2.2.2 Erowid Lycaeum 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA

50 4-D 2.1.1 Erowid Lycaeum 4-Trideuteromethyl-3,5-dimethoxy-PEA

51 beta-D 2.1.4 Erowid Lycaeum beta,beta-Dideutero-3,4,5-trimethoxy-PEA

52 DESOXY 2.1.2 Erowid Lycaeum 4-Methyl-3,5-Dimethoxy-PEA

53 2,4-DMA 2.1.1 Erowid Lycaeum 2,4-Dimethoxy-A



56 DMCPA 2 2 2 E id L2-(2,5-Dimethoxy-4-methylphenyl)


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56 DMCPA 2.2.2 Erowid Lycaeum( , y y p y )

-cyclopropylamine

57 DME 2.1.1 Erowid Lycaeum 3,4-Dimethoxy-beta-hydroxy-PEA

58 DMMDA 2.3.3 Erowid Lycaeum 2,5-Dimethoxy-3,4-methylenedioxy-A

59 DMMDA-2 2.3.3 Erowid Lycaeum 2,3-Dimethoxy-4,5-methylenedioxy-A

60 DMPEA 2.1.1 Erowid Lycaeum 3,4-Dimethoxy-PEA

61 DOAM 2.2.2 Erowid Lycaeum 4-Amyl-2,5-dimethoxy-A

62 DOB 2.2.2 Erowid Lycaeum 4-Bromo-2,5-dimethoxy-A

63 DOBU 2.2.2 Erowid Lycaeum 4-Butyl-2,5-dimethoxy-A

64 DOC 2.2.2 Erowid Lycaeum 4-Chloro-2,5-dimethoxy-A

65 DOEF 2.2.2 Erowid Lycaeum 4-(2-Fluoroethyl)-2,5-dimethoxy-A

66 DOET 2.2.2 Erowid Lycaeum 4-Ethyl-2,5-dimethoxy-A

67 DOI 2.2.2 Erowid Lycaeum 4-Iodo-2,5-dimethoxy-A

68 DOM 2.2.2 Erowid Lycaeum 4-Methyl-2,5-dimethoxy-A

69 -DOM 2.2.2 Erowid Lycaeum 4-Methyl-2,6-dimethoxy-A

70 DON 2.2.2 Erowid Lycaeum 4-Nitro-2,5-dimethoxy-A

71 DOPR 2.2.2 Erowid Lycaeum 4-Propyl-2,5-dimethoxy-A

72 E 2.1.3 Erowid Lycaeum 4-Ethoxy-3,5-dimethoxy-PEA

73 EEE 2.2.1 Erowid Lycaeum 2,4,5-Triethoxy-A

74 EEM 2.2.1 Erowid Lycaeum 2,4-Diethoxy-5-methoxy-A

75 EME 2.2.1 Erowid Lycaeum 2,5-Diethoxy-4-methoxy-A

76 EMM 2 2 1 Erowid Lycaeum 2-Ethoxy-4 5-dimethoxy-A


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76 EMM 2.2.1 Erowid Lycaeum 2-Ethoxy-4,5-dimethoxy-A

77 ETHYL-J 2.3.4 Erowid Lycaeum N,a-diethyl-3,4-methylenedioxy-PEA

78 ETHYL-K 2.3.4 Erowid Lycaeum N-Ethyl-a-propyl-3,4-methylenedioxy-PEA

79 F-2 2.4.2 Erowid LycaeumBenzofuran-2-methyl-5-methoxy

-6-(2-aminopropane)

80 F-22 2.4.2 Erowid Lycaeum Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)

81 FLEA 2.3.2 Erowid Lycaeum N-Hydroxy-N-methyl-3,4-methylenedioxy-A

82 G-3 2.2.3 Erowid Lycaeum 3,4-Trimethylene-2,5-dimethoxy-A

83 G-4 2.2.3 Erowid Lycaeum 3,4-Tetramethylene-2,5-dimethoxy-A

84 G-5 2.2.3 Erowid Lycaeum 3,4-Norbornyl-2,5-dimethoxy-A

85 GANESHA 2.2.3 Erowid Lycaeum 3,4-Dimethyl-2,5-dimethoxy-A

86 G-N 2.2.3 Erowid Lycaeum 1,4-Dimethoxynaphthyl-2-isopropylamine

87 HOT-2 2.2.2 Erowid Lycaeum2,5-Dimethoxy-N-hydroxy

-4-ethylthio-PEA


-4-(n)-propylthio-PEA


-4-(s)-butylthio-PEA

90 IDNNA 2.2.2 Erowid Lycaeum 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A

91 IM 2.1.1 Erowid Lycaeum 2,3,4-Trimethoxy-PEA

92 IP 2.1.2 Erowid Lycaeum 3,5-Dimethoxy-4-isopropoxy-PEA

93 IRIS 2.2.3 Erowid Lycaeum 5-Ethoxy-2-methoxy-4-methyl-A
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94 J 2.3.4 Erowid Lycaeum a-Ethyl-3,4-methylenedioxy-PEA

95 LOPHOPHINE 2.3.3 Erowid Lycaeum 3-Methoxy-4,5-methylenedioxy-PEA

96 M (mescaline) 2.1 Erowid Lycaeum 3,4,5-Trimethoxy-PEA

97 4-MA 2.1.1 Erowid Lycaeum 4-Methoxy-A

98 MADAM-6 2.3.2 Erowid Lycaeum 2,N-Dimethyl-4,5-methylenedioxy-A

99 MAL 2.1.2 Erowid Lycaeum 3,5-Dimethoxy-4-methallyloxy-PEA

100 MDA 2.3 Erowid Lycaeum 3,4-Methylenedioxy-A

101 MDAL 2.3.1 Erowid Lycaeum N-Allyl-3,4-methylenedioxy-A

102 MDBU 2.3.1 Erowid Lycaeum N-Butyl-3,4-methylenedioxy-A

103 MDBZ 2.3.1 Erowid Lycaeum N-Benzyl-3,4-methylenedioxy-A

104 MDCPM 2.3.1 Erowid Lycaeum N-Cyclopropylmethyl-3,4-methylenedioxy-A

105 MDDM 2.3.2 Erowid Lycaeum N,N-Dimethyl-3,4-methylenedioxy-A

106 MDE 2.3.1 Erowid Lycaeum N-Ethyl-3,4-methylenedioxy-A

107 MDHOET 2.3.1 Erowid Lycaeum N-(2-Hydroxyethyl)-3,4-methylenedioxy-A

108 MDIP 2.3.1 Erowid Lycaeum N-Isopropyl-3,4-methylenedioxy-A

109 MDMA 2.3.1 Erowid Lycaeum N-Methyl-3,4-methylenedioxy-A

110 MDMC 2.3.1 Erowid Lycaeum N-Methyl-3,4-ethylenedioxy-A

111 MDMEO 2.3.1 Erowid Lycaeum N-Methoxy-3,4-methylenedioxy-A

112 MDMEOET 2.3.1 Erowid Lycaeum N-(2-Methoxyethyl)-3,4-methylenedioxy-A

113 MDMP 2.3.2 Erowid Lycaeum a,a,N-Trimethyl-3,4-methylenedioxy-PEA
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114 MDOH 2.3.1 Erowid Lycaeum N-Hydroxy-3,4-methylenedioxy-A

115 MDPEA 2.3.1 Erowid Lycaeum 3,4-Methylenedioxy-PEA

116 MDPH 2.3.2 Erowid Lycaeum a,a-Dimethyl-3,4-methylenedioxy-PEA

117 MDPL 2.3.1 Erowid Lycaeum N-Propargyl-3,4-methylenedioxy-A

118 MDPR 2.3.1 Erowid Lycaeum N-Propyl-3,4-methylenedioxy-A

119 ME 2.1.3 Erowid Lycaeum 3,4-Dimethoxy-5-ethoxy-PEA

120 MEDA 2.3.3 Erowid Lycaeum 3,4-Ethylenedioxy-5-methoxy-A

121 MEE 2.2.1 Erowid Lycaeum 2-Methoxy-4,5-diethoxy-A

122 MEM 2.2.1 Erowid Lycaeum 2,5-Dimethoxy-4-ethoxy-A

123 MEPEA 2.1.1 Erowid Lycaeum 3-Methoxy-4-ethoxy-PEA

124 META-DOB 2.2.2 Erowid Lycaeum 5-Bromo-2,4-dimethoxy-A

125 META-DOT 2.2.2 Erowid Lycaeum 5-Methylthio-2,4-dimethoxy-A

126 METHYL-DMA 2.1.1 Erowid Lycaeum N-Methyl-2,5-dimethoxy-A

127 METHYL-DOB 2.2.2 Erowid Lycaeum 4-Bromo-2,5-dimethoxy-N-methyl-A

128 METHYL-J 2.3.4 Erowid Lycaeum N-Methyl-a-ethyl-3,4-methylenedioxy-PEA

129 METHYL-K 2.3.4 Erowid Lycaeum N-Methyl-a-propyl-3,4-methylenedioxy-PEA

130 METHYL-MA 2.1.1 Erowid Lycaeum N-Methyl-4-methoxy-A

131 METHYL-MMDA-2 2.3.3 Erowid Lycaeum N-Methyl-2-methoxy-4,5-methylenedioxy-A

132 MMDA 2.3.3 Erowid Lycaeum 3-Methoxy-4,5-methylenedioxy-A

133 MMDA-2 2.3.3 Erowid Lycaeum 2-Methoxy-4,5-methylenedioxy-A


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134 MMDA-3a 2.3.3 Erowid Lycaeum 2-Methoxy-3,4-methylenedioxy-A

135 MMDA-3b 2.3.3 Erowid Lycaeum 4-Methoxy-2,3-methylenedioxy-A

136 MME 2.2.1 Erowid Lycaeum 2,4-Dimethoxy-5-ethoxy-A

137 MP 2.1.2 Erowid Lycaeum 3,4-Dimethoxy-5-propoxy-PEA

138 MPM 2.2.1 Erowid Lycaeum 2,5-Dimethoxy-4-propoxy-A

139 ORTHO-DOT 2.2.2 Erowid Lycaeum 2-Methylthio-4,5-dimethoxy-A

140 P 2.1.2 Erowid Lycaeum 3,5-Dimethoxy-4-propoxy-PEA

141 PE 2.1.2 Erowid Lycaeum 3,5-Dimethoxy-4-phenethyloxy-PEA

142 PEA 1.2 Erowid Lycaeum PEA

143 PROPYNYL 2.1.2 Erowid Lycaeum 4-Propynyloxy-3,5-dimethoxy-PEA

144 SB 2.1.3 Erowid Lycaeum 3,5-Diethoxy-4-methoxy-PEA

145 TA 2.1.1 Erowid Lycaeum 2,3,4,5-Tetramethoxy-A

146 3-TASB 2.1.3 Erowid Lycaeum 4-Ethoxy-3-ethylthio-5-methoxy-PEA

147 4-TASB 2.1.3 Erowid Lycaeum 3-Ethoxy-4-ethylthio-5-methoxy-PEA

148 5-TASB 2.1.3 Erowid Lycaeum 3,4-Diethoxy-5-methylthio-PEA

149 TB 2.1.2 Erowid Lycaeum 4-Butylthio*-3,5-dimethoxy-PEA

150 3-TE 2.1.2 Erowid Lycaeum 4-Ethoxy-5-methoxy-3-methylthio-PEA

151 4-TE 2.1.2 Erowid Lycaeum 3,5-Dimethoxy-4-ethylthio-PEA

152 2-TIM 2.1.4 Erowid Lycaeum 2-Methylthio-3,4-dimethoxy-PEA



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155 3-TM 2.1.4 Erowid Lycaeum 3-Methylthio-4,5-dimethoxy-PEA

156 4-TM 2.1.4 Erowid Lycaeum 4-Methylthio-3,5-dimethoxy-PEA

157 TMA 2.1.1 Erowid Lycaeum 3,4,5-Trimethoxy-A

158 TMA-2 2.1.1 Erowid Lycaeum 2,4,5-Trimethoxy-A





163 3-TME 2.1.2 Erowid Lycaeum 4,5-Dimethoxy-3-ethylthio-PEA

164 4-TME 2.1.2 Erowid Lycaeum 3-Ethoxy-5-methoxy-4-methylthio-PEA

165 5-TME 2.1.2 Erowid Lycaeum 3-Ethoxy-4-methoxy-5-methylthio-PEA

166 2T-MMDA-3a 2.3.3 Erowid Lycaeum 2-Methylthio-3,4-methylenedioxy-A

167 4T-MMDA-2 2.3.3 Erowid Lycaeum 4,5-Thiomethyleneoxy-2-methoxy-A

168 TMPEA 2.1.1 Erowid Lycaeum 2,4,5-Trimethoxy-PEA

169 2-TOET 2.2.2 Erowid Lycaeum 4-Ethyl-5-methoxy-2-methylthio-A

170 5-TOET 2.2.2 Erowid Lycaeum 4-Ethyl-2-methoxy-5-methylthio-A

171 2-TOM 2.2.2 Erowid Lycaeum 5-Methoxy-4-methyl-2-methylthio-A

172 5-TOM 2.2.2 Erowid Lycaeum 2-Methoxy-4-methyl-5-methylthio-A

173 TOMSO 2.2.2 Erowid Lycaeum 2-Methoxy-4-methyl-5-methylsulfinyl-A


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174 TP 2.1.2 Erowid Lycaeum 4-Propylthio-3,5-dimethoxy-PEA

175 TRIS 2.1.2 Erowid Lycaeum 3,4,5-Triethoxy-PEA

176 3-TSB 2.1.2 Erowid Lycaeum 3-Ethoxy-5-ethylthio-4-methoxy-PEA

177 4-TSB 2.1.2 Erowid Lycaeum 3,5-Diethoxy-4-methylthio-PEA

178 3-T-TRIS 2.1.2 Erowid Lycaeum 4,5-Diethoxy-3-ethylthio-PEA

179 4-T-TRIS 2.1.2 Erowid Lycaeum 3,5-Diethoxy-4-ethylthio-PEA

* Note: The short index at the start of Book II and the indices available online list this as thiobutoxy.

Changes

This file is copyright 2000 rkundalini. Please distribute (unmodified) freely. Given the number of chemicals referenced

in this document, there a re bound to be mistakes, improvements, etc that must be made. To keep things organized,please do not modify this document yourself. Corrections, suggestions and so on are we lcomed, send them to

[email protected].

Version 1.0 (17 Mar 00): Initial revision.

Version 1.1 (11 Apr 00): Expanded introductory PEA material after monkish suggestions.

This text was taken from The Forbidden Fruit
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