BOx, also known asβ-hydroxy- or -methoxy- 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] The BOx drugs weresynthesized and tested byAlexander Shulgin and reported in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).^[1][2]

The BOx drugs include the following, with their effects as reported by Shulgin also specified:^[1][2]

• BOB (4-bromo-2,5,β-trimethoxyphenethylamine) – methoxy BOx analogue of2C-B – altered state of consciousness, tinnitus, tingling, sense of awareness^[1][2]
• BOH-2C-B (β-OH-2C-B) – hydroxy BOx analogue of2C-B – encountered as a noveldesigner drug and presumably a psychedelic
• BOD (4-methyl-2,5,β-trimethoxyphenethylamine) – methoxy BOx analogue of2C-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) – hydroxy BOx analogue of2C-D – marked drop in blood pressure^[1][2]
• BOH (3,4-methylenedioxy-β-methoxyphenethylamine) – methoxy BOx analogue ofMDPEA –slight warmth, mydriasis, anorexia, mild nausea, cold feet, no psychedelic, entactogenic, or euphoriant effects (however nonetheless given a ++ on theShulgin scale)^[1][2]
• BOM (3,4,5,β-tetramethoxyphenethylamine) – methoxy BOx analogue ofmescaline – few or no effects^[1][2]
• DME (3,4-dimethoxy-β-hydroxyphenethylamine) – hydroxy BOx analogue of3,4-dimethoxyamphetamine (3,4-DMA) – few or no effects^[1][2]

Hence, of the BOx drugs, BOD is the only one that produces clear psychedelic effects.^[1][2]

• BOx (psychedelics)
• Chemical classes of psychoactive drugs
• Psychedelic phenethylamines

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