The BOx drugs include the following, with their effects as reported by Shulgin also specified:[1][2]
BOB (4-bromo-2,5,β-trimethoxyphenethylamine; β-methoxy-2C-B) – methoxy BOx analogue of 2C-B – altered state of consciousness, tinnitus, tingling, sense of awareness[1][2]
BOH-2C-B (BOHB; 4-bromo-2,5-dimethoxy-β-hydroxyphenethylamine; β-hydroxy-2C-B) – hydroxy BOx analogue of 2C-B – encountered as a novel designer drug and presumably a psychedelic[3][4]
BOD (4-methyl-2,5,β-trimethoxyphenethylamine; β-methoxy-2C-D) – methoxy BOx analogue of 2C-D – mild open-eye and moderate closed-eye visuals, enhanced conversation and humor, nausea and lethargy[1][2]
BOHD (4-methyl-2,5-dimethoxy-β-hydroxyphenethylamine; β-hydroxy-2C-D) – hydroxy BOx analogue of 2C-D – marked drop in blood pressure[1][2]
BOH (3,4-methylenedioxy-β-methoxyphenethylamine; β-methoxy-MDPEA) – methoxy BOx analogue of MDPEA – slight warmth, mydriasis, anorexia, mild nausea, cold feet, no psychedelic, entactogenic, or euphoriant effects (however nonetheless given a ++ on the Shulgin scale)[1][2]
3C-BOH (BOMDA; 3,4-methylenedioxy-β-methoxyamphetamine; β-methoxy-MDA) – methoxy BOx analogue of 3,4-methylenedioxyamphetamine (MDA) – "amphetamine-like effects", physical side effects, temporary body stiffness[5][6]
BOM (3,4,5,β-tetramethoxyphenethylamine; β-methoxymescaline) – methoxy BOx analogue of mescaline – few or no effects[1][2]
DME (3,4-dimethoxy-β-hydroxyphenethylamine; β-hydroxy-3,4-DMA) – hydroxy BOx analogue of 3,4-dimethoxyamphetamine (3,4-DMA) – few or no effects[1][2]
On the basis of the preceding findings, of the BOx drugs, BOD is the only one known to produce clear psychedelic effects.[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. PMID15537358.
^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"
^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. PMID35378384. 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.
