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Book II of PiHKAL: A Chemical Love Story, by Alexander & Ann Shulgin #101: MDAL
#101 MDAL: N-Allyl-MDA; 3,4-Methylenedioxy-N-allylamphetamine

#101 MDAL SYNTHESIS: A total of about 20 mL allylamine was introduced under the surface of 20 mL concentrated HCl, and the mixture stripped of volatiles under vacuum The resulting 24 g of wet material did not yield any crystals with either acetone or Et2O. This was dissolved in 75 mL MeOH, treated with 4.45 g 3,4-methylenedioxyphenylacetone (see under MDMA for its preparation), and finally with 1.1 g sodium cyanoborohydride. Concentrated HCl was added as needed over the course of 5 days to keep the pH constant at about 6. The reaction mixture was then added to a large amount of H2O, acidified with HCl, and extracted with 3×100 mL CH2Cl2. The aqueous phase was made basic with 25% NaOH, and extracted with 3×100 mL CH2Cl2. Evaporation of the solvent from these extracts yielded 3.6 g of an amber oil which, on distillation at 90–95 °C at 0.2 mm/Hg, yielded 2.6 g of an off-white oil. This was dissolved in 10 mL IPA, neutralized with about 25 drops of concentrated HCl, and the resulting clear but viscous solution was diluted with Et2O until crystals formed. These were removed by filtration, washed with IPA/Et2O (1:1), then with Et2O, and air dried to constant weight. There was thus obtained 2.5 g of 3,4-methylenedioxy-N-allylamphetamine hydrochloride (MDAL) with a mp of 174–176 °C and a proton NMR spectrum that showed that the allyl group was intact. Anal. (C13H18ClNO2) N.

DOSAGE: greater than 180 mg.

DURATION: unknown.

EXTENSIONS AND COMMENTARY: Here is another inactive probe, like MDPR, that could possibly serve as a primer to LSD. The three carbon chain on the nitrogen seen with MDPR is almost identical to the three carbon chain on the nitrogen atom of MDAL. And yet, where an “inactive” level of 180 milligrams of MDPR is a rather fantastic enhancer of LSD action, the same weight of this compound not only does not enhance, but actually seems to somewhat antagonize the action of LSD. All this difference from just a couple of hydrogen atoms. Identical carbon atoms, identical oxygen atoms, and an identical nitrogen atom. And all in identical places. Simply C13H18ClNO2 rather than C13H20ClNO2.

So, apparently, almost identical is not good enough!

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

510 · 934 · 4930 (voice)
510 · 934 · 5999 (fax)