BOx, also known asβ-oxygenated- and ring-substituted phenethylamines, are a group ofpsychedelic and otherpsychoactive drugs of thephenethylamine family.[1][2] They have either ahydroxy group ormethoxy group at the β position of thealkylside chain as well as additionalsubstitutions at the 2 through 5 positions of thephenyl ring.[1][2]
Certain BOx drugs likeBOB (β-methoxy-2C-B) have been found to act asserotonin5-HT2A receptoragonists.[3]
The BOx drugs were described in thescientific literature byAlexander Shulgin,Peyton Jacob III, andDarrell Lemaire in 1985.[4] They were subsequently further described by Shulgin in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).[1][2] Additional BOx drugs likeBOH-2C-B (BOHB; β-hydroxy-2C-B) and3C-BOH (β-methoxy-MDA; BOMDA) were later described byDaniel Trachsel in 2013.[5] In addition, BOHB emerged as a noveldesigner drug.[6]
| Compound | Chemical name | Dose | Duration | Effects |
|---|---|---|---|---|
| BOB (β-methoxy-2C-B) | 4-Bromo-2,5,β-trimethoxyphenethylamine | 10–20 mg | 10–20 hours | Altered consciousness, tinnitus, tingling, awareness[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] |
| 3C-BOH (β-methoxy-MDA) | 3,4-Methylenedioxy-β-methoxyamphetamine | 40–70 mg | 3–6 hours | Stimulation, physical effects, body stiffness[5][7] |
| 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][8][1][5] | ||||
On the basis of the preceding findings, of the BOx drugs, BOD is the only drug clearly known to produce psychedelic effects.[1][2]
Other related compounds likeβk-2C-B (β-keto-2C-B),β-methyl-2C-B (BMB), andβ-methyl-DOM (Daphne, Elvira) have also been described.[5]
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.