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Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #59: DMMDA-2
#59 DMMDA-2: 2,3-Dimethoxy-4,5-methylenedioxyamphetamine

#59 DMMDA-2 DOSAGE: about 50 mg.

DURATION: unknown.

QUALITATIVE COMMENTS: (with 50 mg) “I am into it; it is much like MDA.”

EXTENSIONS AND COMMENTARY: This is pretty sparse information upon which to build a picture of biological activity. First, the synthesis was done by someone else and, as I have not been able to find where the notes are, this will be the one recipe in the footnote without explicit directions incorporated. The procedure used was exactly the same as that described for DMMDA, except that the starting material was dillapiole rather than apiole. The dillapiole was obtained by the careful fractionation of Oil of Dill (as opposed to the isolation of apiole from the careful fractionation of Oil of Parsley). Isomerization to isodillapiole, nitration with tetranitromethane to give 1-(2,3-dimethoxy-4,5-methylenedioxyphenyl)-2-nitropropene, and its reduction with LAH in ether to give 2,3-dimethoxy-4,5-methylenedioxyamphetamine hydrochloride (DMMDA-2) proceeded in a precisely analogous manner to the preparation of DMMDA.

And the pharmacological part is rather thin as well. I was not the taster, and can only quote what I had been given. This same observer found a threshold at 28 milligrams. Under other circumstances, this comment on DMMDA-2 would have been tucked into the commentary on DMMDA where it belongs, but the activity level was called for in a large review article, and on the basis of the above, both its initials and the value of 5× the potency of mescaline were permanently enshrined in the published literature. What is it really like? I don’t know. Its structure is an appealing amalgamation of that of MMDA and MMDA-2, and it might be quite a winner if the dosage and the duration were known. It is, after all, one of the ten essential amphetamines, since dillapiole is one of the ten essential oils.

At the time that DMMDA and DMMDA-2 were synthesized, I had visions of doing the same thorough study with these as I had set up with the TMA’s (six possible, six done) and the MMDA’s (six possible, five done). Here, too, with a pair of methoxy groups on an amphetamine skeleton, with a methylenedioxy ring thrown in, six isomers are possible but only these two have been prepared. The unknown ones will certainly be called DMMDA-3, -4, -5 and -6, but the assignments of code to structure haven’t even been thought out yet. The remarkable and totally unexpected activity of DOM was discovered at about this time and it was a much more tempting direction to follow. The remaining four possible DMMDA’s have been left to that famous time, a future “rainy day.”

Page updated 30 March 2012 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·

About PiHKAL • info

This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Still others remain to be added.

I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore most of the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice, and in the hope of aligning with more readers’ searches. Typically the change is little more than expanding a prefix and setting it in italics. The errata and changes page has further details.

Cautionary Note

“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 herein, 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

Copyright Notice

The copyright for Book I of PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering Information

PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.

Although Sasha and Ann have put Book II of PiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them—and there’s still nothing quite like holding a real book in your hands.

PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.

Transform Press,
Box 13675
Berkeley, CA 94701

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