Quick Index to PiHKAL
By Lamont Granquist
This is the Quick Index to Alexander and Ann Shulgin's Phenethylamine's
i Have Known and Loved. It is not a comprehensive list, but
hopefully points out the major chemicals and things which people "should"
be familiar with. I'm quite sure i've overlooked someone's favorite
chemical in here and that grave injustices have been done. Such is the
nature of trying to provide a condensed version.
See the ordering instructions, copyright and main
index for more complete information.
Active Chemicals
2C-B: 2,5-dimethoxy-4-bromophenethylamine, bromomescaline, CBr
2C-D: 2,5-dimethoxy-4-methylphenethylamine, LE-25
2C-T-2: 2,5-dimethoxy-4-ethylthiophenethylamine
2C-T-7: 2,5-dimethoxy-4-propylthiophenethylamine
DOB: 2,5-dimethoxy-4-bromoamphetamine
DOI: 2,5-dimethoxy-4-iodoamphetamine
DOM: 2,5-dimethoxy-4-methyamphetamine, STP
M: 3,4,5-trimethoxyphenthylamine, Mescaline
MDA: 3,4-methylenedioxyamphetamine
MDE: N-ethyl-3,4-methylenedioxyamphetamine
MDMA: N-methyl-3,4-methylenedioxyamphetamine
MDOH: N-hydroxy-3,4-methylenedioxyamphetamine
MEM: 2,5-dimethoxy-4-ethoxyamphetamine
Methyl-J: N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, MBDB, Eden
MMDA: 3-methoxy-4,5-methylenedioxyamphetamine
TMA: 3,4,5-trimethoxyamphetamine
TMA-2: 2,4,5-trimethoxyamphetamine
TMA-6: 2,4,6-trimethoxyamphetamine
Short Discussion and Background
Mescaline is probably the chemical skeleton
which the bulk of the chemicals in Book II of PiHKAL are based on. It has
the 2-carbon chain phenethylamine (vs. the 3-carbon chain amphetamine)
structure, with the 3,4,5-methoxy- substitution pattern on the phenyl
ring. The 3-carbon amphetamine analog of mescaline
TMA(3,4,5-trimethoxyamphetamine) is an active and more potent drug than
mescaline itself. A
rearrangement of the substitutents on the phenyl ring gives TMA-2 and TMA-6 which
are about 5 times more potent than TMA (Others:
TMA-3,TMA-4,
TMA-5). The 2,4,5-trimethoxy pattern
of TMA-2 (it being the most potent) was further investigated by trying
ethoxy- instead of methoxy- substitutents and in all combinations. The
4-substituted 2,5-dimethoxy-4-ethyoxyamphetamine (
MEM) was found to be the most potent of these analogs (Others:
EMM, MME,
EEM, EME,
MEE). The potency of MEM led to attempts
to try different modifications to the 4-position of TMA-2. The
4-bromo- (DOB), 4-iodo- (DOI) and 4-methyl- (DOM)
substituted amphetamines are probably the most interesting and highly
potent chemicals
(Others: DOAM, DOBU,
DOC, DOEF,
DOET, DON,
DOPR). Radioactively labelled DOB and DOI
are used as neurochemical probes and DOB is the most potent
phenethylamine in this book. DOM wound up on the street market as "STP"
in the late 60's. There are also sulfer containing modifications to the
4-position of the amphetamines (ALEPH,
ALEPH-2, ALEPH-4,
ALEPH-6, ALEPH-7)
some of which are highly potent, but which seem to produce states lacking in
empathy. The 2-carbon phenethylamine analogs of DOB and DOM are,
respectively, 2C-B and
2C-D (Other similar 2-carbon analogs of
amphetamines: 2C-C,
2C-E, 2C-F,
2C-I, 2C-N,
2C-O-4, 2C-P,
2C-SE). Both 2C-B and 2C-D are
very potent. 2C-B is useful in conjunction with MDMA and it has achieved
enough attention in the market to have been placed
in Schedule I by the U.S. DEA. The 4-substituted
sulfer-containing 2-carbon analogs of the ALEPHs contain
2C-T-2 and
2C-T-7 which are useful adjuncts to
MDMA therapy similar to 2C-B, 2C-T-21 is also
strongly active (Others: 2C-T,
2C-T-4,
2C-T-8, 2C-T-9,
2C-T-13, 2C-T-15,
2C-T-17).
Changing gears somewhat, the joining of two of the methoxy- substitutents
of TMA into a methylenedioxy- ring gives MMDA.
(Using other TMAs Gives: MMDA-2,
MMDA-3a, MMDA-3b
, MMDA-4, MMDA-5). MMDA is simply 3-methoxy-MDA and is sort of the
bridge between Mescaline and the MDA family of chemicals.
MDA is the parent chemical and
MDMA and MDE
are N-methyl- and N-ethyl-MDA, respectively. MDMA is, of course, "Ecstasy"
or "Adam" which has gotten a substantial amount of attention. MDE or MDA
are often sold as "Ecstasy" instead of MDMA. Also occasionally seen on the
market is
MDOH which is N-hydroxy-MDA. Extending the
3-carbon chain of MDMA to a 4-carbon chain produces Methyl-Jor MBDB. Other interesting chemicals
are the "classic ladies" which are DOM analogs that have been systematically
methylated at each possible hydrogen in DOM, and in particular the
Ganesha 3,4-substituted- 2,5-dimethoxyamphetamines and their 2-carbon
counterparts, and then there are the various N-substituted analogs of
many chemicals and some chemicals which represent minor variations
in the book rather than a theme. I'll let you find those for yourself.
Sasha's Commentaries
A Quick Chemical Glossary
I can't hope to teach anyone chemistry in a short space, but hopefully
this glossary will help to give some meaning to the syntheses for those
who have only a little chemistry.
- CH2Cl2: Dichloromethane; Methylene Chloride. Solvent. Related
to chloroform (trichloromethane).
- CH3CN:
- Et2O: (C2H5)2O; Diethyl Ether. Solvent. Peroxidizes on exposure
to air, dangerous.
- EtOH: C2H5OH; Ethanol; Ethyl Alcohol. Solvent.
- H2O: Hydrogen oxide; Water. Solvent.
- H2SO4: Sulfuric Acid. Strong Acid.
- HCl: Hydrochloric Acid; Muriatic Acid. Strong acid.
- He: Helium gas. Inert Atmosphere.
- IPA: C3H7OH; Isopropanol; Isopropyl Alcohol. Solvent.
- KOH: Potassium Hydroxide. Strong Base.
- K2CO3: Potassium Carbonate; Potash. Weak Base.
- LAH: LiAlH4; Lithium Aluminum Hydride. Reducing Agent.
Explodes on contact with water -- used only under N2
atmosphere. Extremely dangerous.
- MeOH: CH3OH; Methanol; Methyl Alcohol. Solvent.
- N2: Nitrogen gas. Inert Atmosphere.
- NaBH3CN: Sodium Cyanoborohydride. Reducing Agent.
- Na2CO3: Sodium Carbonate; Soda Ash. Weak Base.
- NMR: Proton Nuclear Magnetic Resonance Spectroscopy. Analytical
technique to determine structure of a compound.
- NaOH: Sodium Hydroxide; Lye. Strong Base.
- POCl3: Phosphorous Oxychloride. Reducing Agent.
- THF: C4H8O; Tetrahydrofuran (cyclized diethyl ether). Solvent.
Peroxidizes on exposure to air, perhaps slightly more
dangerous than Et2O.
- TLC: Thin-Layer Chromatography. Analytical technique to
determine composition of a sample.
October 31, 1994 | lamont@hyperreal.com