N,O-DMS · nor-5-MeO-DMT · Tryptamine, 5-methoxy-N-methyl · Indole, 5-methoxy-3-[2-(methylamino)ethyl] · Serotonin, N,O-dimethyl · 5-Methoxy-N-methyltryptamine · 5-Methoxy-3-[2-(methylamino)ethyl]indole · N,O-Dimethylserotonin
#42 5-MeO-NMT SYNTHESIS: (from ). To a solution of 0.10 g 5-methoxy-N,N-dimethyl tryptamine 5-methoxy-N,N-dimethyltryptamine (see 5-MeO-DMT) in 5 mL benzene there was added 0.5 g 2,2,2-trichloroethyl chloroformate, and the resulting solution was held at reflux temperature for 2 days. After cooling there was added 5 mL Et2O and the organic phase washed with 2×20 mL 3 N HCl followed by 20 mL H2O. The solvent was then removed under vacuum. The residue (N-(2,2,2-trichloroethoxycarbonyl)-N-methyl-5-methoxytryptamine, 0.12 g) was dissolved in 2 mL acetic acid and treated with 0.15 g powdered zinc. After stirring for 4 h at room temperature, the reaction mixture was filtered and the filtrate made basic with 3 N NaOH. This was extracted with 3×20 mL Et2O, the extracts pooled, and the solvent removed under vacuum. The residue was purified by preparative TLC, using a n-BuOH/AcOH/H2O (12/3/5) solvent for development. There was thus obtained 0.013 g of 5-methoxy-N-methyltryptamine (5-MeO-NMT) as a solid with a mp of 90–93 °C.
(from ) A solution of 0.086 g 5-methoxytryptamine (5-MeO-T) in 1 mL dioxane containing 0.5 mL of 2 N NaOH was cooled to 0 °C and well-stirred. There was added, at the same time, 0.2 mL benzyl chloroformate and 0.25 mL 4 N NaOH. This was allowed to come to room temperature and the stirring was continued for an additional 10 min. There was added concentrated HCl, followed by 10 mL H2O. This mixture was extracted with 3×20 mL Et2O, the extracts pooled, and the solvent removed under vacuum. The crude carbamate was purified by silica-gel column chromatography using n-hexane/CH2Cl2 (1/9) as an eluting solvent. After removal of the chromatographic solvent under vacuum, the residue was dissolved in 10 mL anhydrous THF and added slowly to a ice-cold, well-stirred suspension of 0.178 g LAH in 10 mL anhydrous THF. After being brought to reflux and held there for 4 h, the mixture was cooled and acidified with 1 N HCl. The THF was removed under vacuum, and the aqueous residue washed with Et2O. This was then treated with solid NaHCO3 and extracted with 3×50 mL Et2O. The solvent from the combined extract was removed under vacuum, and the residue purified by preparative TLC as described above. There was thus obtained 0.016 g of 5-MeO-NMT with a mp of 88–91 °C.
DOSAGE: (not known)
DURATION: (not known)
EXTENSIONS AND COMMENTARY: This base is the botanically and pharmacologically famous , missing one of its two N-methyl groups. Sort of a nor-5-MeO-DMT. Its human exploration has just been started, but the expected vulnerability of it to metabolic oxidative deamination makes it a good guess that it (as seen with the dimethyl homologue) will only be active parenterally, or when the body’s destructive enzymes are held at bay by effective monoamine oxidase inhibition. This base has been found in several Virola species but, as it is always accompanied by 5-MeO-DMT, its contribution to the psychoactivity of the resulting snuff is completely unknown. It has also been found in the skin of the Bufo alvarius at the trivial level of 20–23 micrograms per gram, compared to skin levels of 1.0 to 3.5 mg/g of 5-MeO-DMT.
A fascinating cyclization product of this “nor-compound” is a cyclic dehydrogenation product where there is a direct coupling of the tryptamine nitrogen to the 4-position of the indole ring. This tricyclic material, O-methylnordehydrobufotenine, proved to be of comparable activity to in rat studies, but has not apparently been studied in man.
13 May 2016 · Creative Commons BY-NC-SA ·

About TiHKAL · info

This version of Book II of TiHKAL is based on the Erowid online version created by Bo Lawler with the help of Erowid, from content generously provided in electronic format by the Authors.
The Erowid online version does not always align precisely with the printed version. Text appears to have been inserted, deleted, or changed at various points. Where the two are seen to diverge both the Erowid and print versions are given. Sharp-eyed readers are encouraged to report novel discrepancies.
As with PiHKAL, I’ve again attempted to reproduce the typographic style of the printed edition. I’ve again 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.

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

Ordering information

TiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of tryptamines. 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 TiHKAL 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.
TiHKAL (ISBN 0-9630096-9-9) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.
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