PIHKAL: A Chemical Love Story

Phenethylamines I Have Known and Loved, Part 2

Part 2: The Chemical Story

By Alexander Shulgin and Ann Shulgin

Index to the Indices

• Index to the Indices
• Copyright Notice
• Introduction
• Cautionary Note
• Info on the HTML version of PiHKAL
• Ordering Information
• Discussion and Background by Lamont Grandquist
• Index of Sasha's Commentaries
• Index to the Phenethylamines

Copyright Notice

Introduction

Please forgive any typos or misprints in this file; further, because of ASCII limitations, many of the typographical symbols in the original book could not be properly represented in these files. -- Simson Garfinkle

Cautionary Note: READ BEFORE PROCEEDING

At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings.... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herin, without being familiar with that drug's action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law. -- Alexander T. Shulgin

Info on the HTML version of PiHKAL

Note: Intermediate chemicals which are used in other syntheses have been written in boldface. This is to make it easier to quickly follow links from one synthesis to another. Unfortunately, it also means that those intermediate chemicals which are used in other syntheses will stand out in boldface for no obviously discernable reason from the immediate context. If someone who is skilled at writing HTML documents knows of a better way to accomplish what i'm trying to do, please drop me a note about it.

PiHKAL was coverted into an HTML document by Lamont Granquist with the permission of the author Alexander Shulgin. Any comments on the HTML version should be sent to me. I can also forward appropriate comments to the author if they are e-mailed to me.

I'd also like to note that if you buy the book you get an extensive commentary on the Shulgin's personal experiences with phenethylamines, the appendicies, diagrams of all the 179 chemicals in book 2, the correct typesettings for the non-ASCII letters and you get a text which is less likely to have typographical errors. Plus if you don't buy it and just leach this copy, your conscience will haunt you till the day you die. BUY IT! BUY IT! BUY IT!!!! ( Dammit, where's my valium? )-- lamontg@u.washington.edu

Ordering Information

Short Discussion and Background

by Lamont Grandquist

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-J or 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

• Essential Amphetamines: Amphetamines derived from essential oils (must read!)
• Phenethylamine: Background on phenethylamine chemistry
• Thio Derivatives: Sulfer-for-Oxygen exchanges
• Classic Ladies: Methyl-for-Hydrogen exchanges in DOM

Index to the Phenethylamines