BOM (drug)

BOM
Clinical data
Other names3,4,5,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 classPsychoactive drug
ATC code
  • None
Identifiers
  • 2-methoxy-2-(3,4,5-trimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO4
Molar mass241.287 g·mol−1
3D model (JSmol)
  • COc1c(cc(cc1OC)C(CN)OC)OC
  • InChI=1S/C12H19NO4/c1-14-9-5-8(11(7-13)16-3)6-10(15-2)12(9)17-4/h5-6,11H,7,13H2,1-4H3 Y
  • Key:GAKIJEPUVBHWCK-UHFFFAOYSA-N Y
  (verify)

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

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BOM's dose as greater than 200 mg orally and its duration as unknown.[1] Some indications of threshold central effects were observed at doses of 120 and 180 mg 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 400 mg orally according to Shulgin, but this remains unknown.[1]

Chemistry

Synthesis

The chemical synthesis of BOM has been described.[1][2]

Analogues

Analogues of BOM include β-hydroxymescaline (β-HOM), BOH (β-methoxy-MDPEA), BOD (β-methoxy-2C-D), and DME (β-hydroxy-3,4-DMPEA), among others.[1][3][4]

History

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

Canada

BOM is not a controlled substance in Canada as of 2025.[7]

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[8]

See also

References

  1. ^ a b c d e f g h i Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. BOM Entry
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  8. ^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.
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