N-Methyl-DOM · 2,5-Dimethoxy-4,N-dimethylamphetamine
SYNTHESIS: A fused sample of 5.0 g of white, crystalline free base 2,5-dimethoxy-4-methylamphetamine,
To a stirred suspension of 4.0 g LAH in 250 mL anhydrous Et2O at reflux and under an inert atmosphere, there was added, by the shunted Soxhlet technique, 4.2 g of 2,5-dimethoxy-N-formyl-4-methylamphetamine as rapidly as its solubility in hot Et2O would allow. The mixture was held at reflux for 24 h and then stirred at room temperature for several additional days. The excess hydride was destroyed with the addition of dilute H2SO4 (20 g in 500 mL water) followed by the additional dilute H2SO4 needed to effect a clear solution. The Et2O was separated, and the aqueous phase extracted with 100 mL Et2O and then with 2×250 mL CH2Cl2. Following the addition of 100 g potassium sodium tartrate, the mixture was made basic with 25% NaOH. The clear aqueous phase was extracted with 3×250 mL CH2Cl2 These extracts were pooled, and the solvent removed under vacuum. The residual amber oil was dissolved in 400 mL anhydrous Et2O, and saturated with hydrogen chloride gas. The white crystals that formed were removed by filtration, washed with Et2O, and air dried to constant weight. There was obtained 4.2 g of product with a mp of 131.5–133.5 °C. This product was recrystallized from 175 mL boiling ethyl acetate to give 3.5 g 2,5-dimethoxy-4,N-dimethylamphetamine hydrochloride (BEATRICE) as pale pink crystals with a mp of 136–137 °C. A sample obtained from a preparation that employed the methyl sulfate methylation of the benzaldehyde adduct of
DOSAGE: above 30 mg.
DURATION: 6–10 h.
QUALITATIVE COMMENTS: (with 20 mg) “There was a gentle and demanding rise from the one to the three hour point that put me into an extremely open, erotic, and responsive place. I had to find a familiar spot to orient myself, and the kitchen served that need. As the experience went on, it showed more and more of a stimulant response, with tremor, restlessness, and a bit of trouble sleeping. But there was no anorexia! An OK experience.”
(with 30 mg) “There is a real physical aspect to this, and I am not completely happy with it. There is diarrhea, and I am restless, and continuously aware of the fact that my body has had an impact from something. The last few hours were spent in talking, and I found myself still awake some 24 hours after the start of the experiment. The mental was not up there to a +++, and yet the physical disruption was all that I might care to weather, and exceeds any mental reward. When I did sleep, my dreams were OK, but not rich. Why go higher?”
EXTENSIONS AND COMMENTARY: This is another example of the N-methyl homologues of the psychedelics. None of them seem to produce stuff of elegance. It is clear that the adding of an N-methyl group onto
In browsing through my notes I discovered that I had made another N-substitution product of 16H23NO3) C,H,N. This reduced smoothly to the corresponding amine,
N-cyclopropyl-2,5-dimethoxy-4-methylamphetamine which formed a hydrochloride salt melting at 153–156 °C. I can’t remember the reasoning that led to this line of synthesis, but it must not have been too exciting, as I never tasted the stuff.
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 history 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,
Berkeley, CA 94701
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