β-Hydroxymescaline (β-HOM), also known as mescalol or as β-hydroxy-3,4,5-trimethoxyphenethylamine, is a psychoactive drug and alkaloid of the phenethylamine, scaline, and BOx families related to the psychedelic drug mescaline.[1][2][3] It has been reported to be naturally occurring in the Pereskia grandiflora cactus.[2][4] The drug may also be a minor metabolite of mescaline formed by dopamine β-hydroxylase (DBH).[5][3][6][7]
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| Other names | Mescalol; β-Hydroxy-3,4,5-trimethoxyphenethylamine; β-HOM |
| Drug class | Psychoactive drug |
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| Formula | C11H17NO4 |
| Molar mass | 227.260 g·mol−1 |
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It is behaviorally active in the conditioned avoidance response (CAR) test in animals similarly to mescaline, but was 7-fold less potent than mescaline.[8] Due to its hydroxyl group and reduced lipophilicity, β-hydroxymescaline shows lower blood–brain barrier penetration than mescaline and is more peripherally selective.[8] Other biological effects of β-hydroxymescaline have also been reported.[2][1][3]
The chemical synthesis of β-hydroxymescaline has been described.[1][2][9]
β-Hydroxymescaline was first described in the scientific literature by 1944.[10][2][1]
See also
editReferences
edit- 1 2 3 4 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- 1 2 3 4 5 "TroutsNotes". isomerdesign.com.
- 1 2 3 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
- ↑ Doetsch PW, Cassady JM, McLaughlin JL (1980). "Cactus alkaloids". Journal of Chromatography A. 189 (1): 79–85. doi:10.1016/S0021-9673(00)82285-2.
- ↑ Dinis-Oliveira RJ, Pereira CL, da Silva DD (2019). "Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions". Current Molecular Pharmacology. 12 (3): 184–194. doi:10.2174/1874467211666181010154139. PMC 6864602. PMID 30318013.
Similar to some biogenic amines, it has been suggested that mescaline could be bioactivated by dopamine-β-hydroxylase, leading to the formation of β-hydroxymescaline [88]. Nevertheless, the formation of this metabolite has not yet been detected in animal or human models [76].
- ↑ Tang Y, Xu L, Guo Z, Zhao J, Xiao Y, Xiang P, et al. (June 2025). "Metabolism study of two phenethylamine - derived new psychoactive substances using in silico, in vivo, and in vitro approaches". Archives of Toxicology. 99 (6): 2367–2378. doi:10.1007/s00204-025-04010-6. PMID 40064698.
Previous studies have suggested that mescaline could be bioactivated by dopamine-β-hydroxylase, similar to the activation of some biogenic amines, which would lead to the formation of β-hydroxymescaline (Goldstein and Contrera 1962). Taking both the literature results and the actual results from this study into consideration, the reaction position of monohydroxylation of proscaline and methallylescaline was concluded to be on the β-carbon, which was consistent with the fragment ion analysis.
- ↑ Creveling CR, Daly JW, Witkop B, Undenfriend S (October 1962). "Substrates and inhibitors of dopamine-beta-oxidase". Biochimica et Biophysica Acta. 64: 125–134. doi:10.1016/0006-3002(62)90765-5. PMID 14023834.
- 1 2 Cohen I, Fischer JF, Vogel WH (March 1974). "Physiological disposition of beta-phenylethylamine, 2,4,5-trimethoxyphenylethylamine, 2,3,4,5,6-pentamethoxyphenylethylamine and beta-hydroxymescaline in rat brain, liver and plasma". Psychopharmacologia. 36 (1): 77–84. doi:10.1007/BF00441384. PMID 4838506.
- ↑ Friedman OM, Parameswaran KN, Burstein S (May 1963). "Synthesis of Phenethylamines Related to Mescaline as Possible Psychotomimetic Agents 1". Journal of Medicinal Chemistry. 6 (3): 227–229. doi:10.1021/jm00339a002. PMID 14185972.
- ↑ Iwamoto HK, Hartung WH (1944). "Amino Alcohols. XIV. Methoxyl Derivatives of Phenylpropanolamine and 3,5-DIHYDROXYPHENYLPROPANOLAMINE (1)". The Journal of Organic Chemistry. 09 (6): 513–517. doi:10.1021/jo01188a004. ISSN 0022-3263.