BOx (psychedelics)
BOx, also known as β-oxygenated- and ring-substituted phenethylamines, are a group of psychedelic and other psychoactive drugs of the phenethylamine family.[1][2] They have either a hydroxy group or methoxy group at the β position of the alkyl side chain as well as additional substitutions at the 2 through 5 positions of the phenyl ring.[1][2]
Certain BOx drugs like BOB (β-methoxy-2C-B) have been found to act as serotonin 5-HT2A receptor agonists.[3]
The BOx drugs were described in the scientific literature by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985.[4] They were subsequently further described by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2] Additional BOx drugs like BOH-2C-B (BOHB; β-hydroxy-2C-B) and 3C-BOH (β-methoxy-MDA; BOMDA) were later described by Daniel Trachsel in 2013.[5] In addition, BOHB emerged as a novel designer drug.[6]
Use and effects
[edit]| Compound | Chemical name | Dose | Duration | Effects |
|---|---|---|---|---|
| BOB (β-methoxy-2C-B) | 4-Bromo-2,5,β-trimethoxyphenethylamine | 10–20 mg | 10–20 hours | Visuals, altered state, tingling, tinnitus[1][2] |
| BOHB (β-hydroxy-2C-B) | 4-Bromo-2,5-dimethoxy-β-hydroxyphenethylamine | ≥30 mg | Unknown | Novel designer drug, presumable psychedelic[3][6] |
| BOD (β-methoxy-2C-D) | 4-Methyl-2,5,β-trimethoxyphenethylamine | 15–25 mg | 8–16 hours | Visuals, enhanced conversation, nausea, lethargy[1][2] |
| BOED (β-ethoxy-2C-D) | 4-Methyl-2,5-dimethoxy-β-ethoxyphenethylamine | 70–75 mg | 10 hours | Intoxication, no visuals, appetite loss, diuresis[2] |
| BOHD (β-hydroxy-2C-D) | 4-Methyl-2,5-dimethoxy-β-hydroxyphenethylamine | >50 mg | Unknown | Marked drop in blood pressure[1][2] |
| BOH (β-methoxy-MDPEA) | 3,4-Methylenedioxy-β-methoxyphenethylamine | 80–120 mg | 6–8 hours | Warmth, mydriasis, anorexia, nausea, cold feet[1][2] |
| BOHH (β-hydroxy-MDPEA) | 3,4-Methylenedioxy-β-hydroxyphenethylamine | >100 mg | Unknown | Few or no effects[2][7] |
| 3C-BOH (β-methoxy-MDA) | 3,4-Methylenedioxy-β-methoxyamphetamine | 40–70 mg | 3–6 hours | Stimulation, physical effects, body stiffness[5][8] |
| BOM (β-methoxymescaline) | 3,4,5,β-Tetramethoxyphenethylamine | >200 mg | Unknown | Few or no effects[1][2] |
| β-HOM (β-hydroxymescaline) | 3,4,5-Trimethoxy-β-hydroxyphenethylamine | Unknown | Unknown | Unknown[1] |
| DME (β-hydroxy-3,4-DMPEA) | 3,4-Dimethoxy-β-hydroxyphenethylamine | >115 mg | Unknown | Few or no effects[1][2] |
| Refs: [2][7][1][5] | ||||
On the basis of the preceding findings, of the BOx drugs, BOB and BOD are the only drugs clearly known to produce psychedelic effects.[1][2]
Interactions
[edit]Related compounds
[edit]Other related compounds like βk-2C-B (β-keto-2C-B), β-methyl-2C-B (BMB), and β-methyl-DOM (Daphne, Elvira) have also been described.[5]
See also
[edit]- Substituted methoxyphenethylamine
- Butaxamine (β-hydroxy-N-tert-butyl-2,5-DMA)
- Desglymidodrine (β-hydroxy-2C-H)
- Dimetofrine (β-hydroxy-N-methyl-4-O-desmethylmescaline)
- Methoxamine (β-hydroxy-2,5-DMA)
- Midodrine (β-hydroxy-N-(aminoethanonyl)-2C-H)
References
[edit]- 1 2 3 4 5 6 7 8 9 10 11 12 13 Shulgin, A.; Manning, T.; Daley, P.F. (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 6 7 8 9 10 11 12 13 14 Alexander T. Shulgin; Ann Shulgin (1991). PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OCLC 25627628.
- 1 2 Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem. 47 (24): 6034–6041. doi:10.1021/jm040082s. PMID 15537358.
- ↑ Lemaire D, Jacob P, Shulgin AT (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". J Pharm Pharmacol. 37 (8): 575–577. doi:10.1111/j.2042-7158.1985.tb03072.x. PMID 2864422.
- 1 2 3 4 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. pp. 583, 833–834. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
- 1 2 https://isomerdesign.com/bitnest/external/EMCDDA/1-June-2020 "As of 16 June 2020, a total of 14 new psychoactive substances have been formally notified by the Member States so far this year. These comprise: • Arylalkylamines: 2 (BOH-PHP, BOH-2C-B)" [...] "14.BOH-2C-B (2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanol) — arylalkylamine, customs seizure, Sweden, 9 April 2020 (also seized by Danish customs on 6 December 2019). Notified: 9 June 2020. EU-EWS-RCS-FN-2020-0014"
- 1 2 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025.
- ↑ Kolaczynska KE, Ducret P, Trachsel D, Hoener MC, Liechti ME, Luethi D (June 2022). "Pharmacological characterization of 3,4-methylenedioxyamphetamine (MDA) analogs and two amphetamine-based compounds: N,α-DEPEA and DPIA". Eur Neuropsychopharmacol. 59: 9–22. doi:10.1016/j.euroneuro.2022.03.006. PMID 35378384.
3C-BOH has been described to have amphetamine-like effects in humans at doses of 40–70 mg, with a duration of 3–6 h (Trachsel et al., 2013). 3C-BOH can exist as four stereoisomers; the pharmacological assessment of each individual isomer is therefore necessary to gain insight into their effects.