Book II of PiHKAL: A Chemical Love Story. Alexander & Ann Shulgin #58: DMMDA
SYNTHESIS: essential oil 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by careful fractional distillation. It is the fraction that boils at 165–167 °C at 27 mm/Hg. A solution of 19.8 g apiole in a mixture of 43 g KOH and 60 mL hot EtOH was heated in the steam bath for 24 h. With vigorous stirring, it was diluted with H2O, at a rate which the crystals that formed spontaneously could accumulate from the turbidity that was generated. When no more H2O could be added (there was persistent oiling out of material) the reaction mixture was filtered to give 12.1 g of an amber solid material. This was recrystallized from 20 mL boiling hexane, which was filtered while hot to remove insolubles. From the cooled filtrate, there was obtained 9.3 g of 2,5-dimethoxy-3,4-methylenedioxy-1-propenylbenzene,
A stirred solution of 8.8 g 2,5-dimethoxy-3,4-methylenedioxy-1-propenylbenzene and 3.9 g pyridine in 45 mL acetone was cooled to ice-bath temperatures, and treated with 7.9 g tetranitromethane. This extremely dark reaction was stirred at 0 °C for 5 min, then quenched with a solution of 2.6 g KOH in 45 mL H2O. With continued stirring, there appeared yellow crystals of 1-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene which, after filtering, washing with 50% acetone and air drying, weighed 8.0 g and had a mp of 110–111 °C.
To a well-stirred and gently refluxing suspension of 6.3 g LAH in 500 mL anhydrous Et2O, under an inert atmosphere, there was added 7.5 g 1-(2,5-dimethoxy-3,4-methylenedioxyphenyl)-2-nitropropene by leaching out the nitrostyrene from a thimble in a modified Soxhlet condenser apparatus. The addition took 1.5 h, and the refluxing was maintained for an additional 3 h. After cooling, the excess hydride was destroyed by the cautious addition of 300 mL of 1.5 N H2SO4. The aqueous phase was brought to a pH of 6 with Na2CO3. This was heated to 80 °C and clarified by filtration though paper. The addition of a stochiometric amount of picric acid in boiling EtOH gave rise to precipitation of the product picrate as globs that did not crystallize. These were washed with cold H2O, then dissolved in 30 mL 5% NaOH. Extraction with 2×75 mL Et2O, and the stripping of the solvent from the pooled extracts, gave 3.1 g of an oily residue which, upon dissolving in 250 mL Et2O and saturation with anhydrous HCl gas, gave white crystals. These were removed by filtration, Et2O-washed, and air dried, to give 2.9 g of 2,5-dimethoxy-3,4-methylenedioxyamphetamine hydrochloride (DMMDA) that melted in the 165–175 °C range.
DOSAGE: 30–75 mg.
DURATION: 6–8 h.
QUALITATIVE COMMENTS: (with 25 mg) “The intoxication was there at an hour and a quarter, and I was hit with nausea with no particular warning. I am shaky, a little dilated in the eyes, and there is a modest depersonalization (reminding me of
(with 32 mg) “I am up to a 2 1/2 plus at something after two hours, with no apparent visuals, no push, no erotic. And a few hours later it is quietly slipping away. It felt completely safe, and without any conspicuous psychedelic action, at least at this level.”
(with 50 mg) “I took graded doses of 10 milligrams every thirty minutes for a total of 50 milligrams, and there were no effects at all.”
(with 50 mg) “In the middle of this all, I found myself getting into abstract thinking, and maybe some imagery as well. The effects were disappointingly light.”
(with 75 mg) “This was equal to somewhere between 75 and 100 micrograms of
EXTENSIONS AND COMMENTARY: DMMDA was the first of the tetraoxygenated amphetamine derivatives that was ever explored in man, back in 1962. And it is not easy to find an acceptable single phrase to describe its action or an acceptable number to describe its potency. I have put the value of 10
The essential oil that corresponds to DMMDA is, of course, essential oils and DMMDA is one of the ten essential amphetamines.
Several people have asked me what I thought about the potential activity of a compound with a methyl group added to DMMDA. One of these possibilities would be the N-methylated derivative, 2,5-dimethoxy-N-methyl-3,4-methylenedioxyamphetamine, or METHYL-DMMDA (or
The placement of an added methyl group onto the beta-position of DMMDA, rather than on the nitrogen atom, produces a pair of stereoisomeric homologues. These are the threo- (or-trans-) and erythro- (or cis)-2,5-dimethoxy-β-methyl-3,4-methylenedioxyamphetamines. They have never been assigned trivial names (my original codes for them were
The only other beta-methyl homologue of an active material that was explored chemically, was related to
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. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The errata and changes page has further details.
“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.”
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.
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.
Though 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,
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