BOM (drug)
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| Other names | 3,4,5,β-Tetramethoxyphenethylamine; β-Methoxymescaline; β-MeO-mescaline; β-MeO-3,4,5-TMPEA; β-Methoxy-3,4,5-TMPEA; β-MeO-TMPEA |
| Routes of administration | Oral [1] |
| Drug class | Psychoactive drug |
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| Chemical and physical data | |
| Formula | C12H19NO4 |
| Molar mass | 241.287g·mol−1 |
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BOM, also known as 3,4,5,β-tetramethoxyphenethylamine or as β-methoxymescaline, is a psychoactive drug of the phenethylamine, scaline, and BOx families related to mescaline.[1] It is the β-methoxy derivative of mescaline.[1]
Use and effects
[edit ]In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOM's dose as greater than 200mg orally and its duration as unknown.[1] Some indications of threshold central effects were observed at doses of 120 and 180mg orally, but higher doses were not explored.[1] BOx drugs are known to be less potent than their non-β-substituted counterparts, so BOM might be active in the range of 200 to 400mg orally according to Shulgin, but this remains unknown.[1]
Chemistry
[edit ]Synthesis
[edit ]The chemical synthesis of BOM has been described.[1] [2]
Analogues
[edit ]Analogues of BOM include β-hydroxymescaline (β-HOM; mescalol), BOH (β-methoxy-MDPEA), BOD (β-methoxy-2C-D), and DME (β-hydroxy-3,4-DMPEA), among others.[1] [3] [4]
History
[edit ]BOM was briefly mentioned by Abram Hoffer and Humphrey Osmond in their 1967 book The Hallucinogens.[5] Subsequently, it was described in greater detail by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985.[6] In addition, it was described in further detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
[edit ]Legal status
[edit ]Canada
[edit ]BOM is not a controlled substance in Canada as of 2025.[7]
United Kingdom
[edit ]This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[8]
See also
[edit ]References
[edit ]- 1 2 3 4 5 6 7 8 9 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. BOM Entry
- ↑ Torres MA, Cassels B, Rezende MC (1995). "The Preparation of Potentially Psychoactive β-Alkoxyphenethylamines". Synthetic Communications. 25 (8): 1239–1247. doi:10.1080/00397919508012687. ISSN 0039-7911 . Retrieved 16 November 2025.
- ↑ Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ↑ Friedman OM, Parameswaran KN, Burstein S (May 1963). "Synthesis of Phenethylamines Related to Mescaline as Possible Psychotomimetic Agents1". Journal of Medicinal Chemistry. 6 (3): 227–229. doi:10.1021/jm00339a002. PMID 14185972.
- ↑ Hoffer A, Osmond H (1967). "Plant β-Phenethylamines". The Hallucinogens. Elsevier. pp. 1–81. doi:10.1016/b978-1-4832-3296-6.50004-5. ISBN 978-1-4832-3296-6 . Retrieved 16 November 2025.
- ↑ Lemaire D, Jacob P, Shulgin AT (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". The Journal of Pharmacy and Pharmacology. 37 (8): 575–577. doi:10.1111/j.2042-7158.1985.tb03072.x. PMID 2864422.
- ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
- ↑ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.