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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, main index, and chemical glossary 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.


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