BOx, also known as β-hydroxy- or -methoxy- 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] The BOx drugs were synthesized and tested by Alexander Shulgin and reported in his 1991 book PiHKAL (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 of 2C-B – altered state of consciousness, tinnitus, tingling, sense of awareness^[1][2]
• BOH-2C-B (β-OH-2C-B) – hydroxy BOx analogue of 2C-B – encountered as a novel designer drug and presumably a psychedelic
• BOD (4-methyl-2,5,β-trimethoxyphenethylamine) – 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) – hydroxy BOx analogue of 2C-D – marked drop in blood pressure^[1][2]
• BOH (3,4-methylenedioxy-β-methoxyphenethylamine) – 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]
• BOM (3,4,5,β-tetramethoxyphenethylamine) – methoxy BOx analogue of mescaline – few or no effects^[1][2]
• DME (3,4-dimethoxy-β-hydroxyphenethylamine) – hydroxy BOx analogue of 3,4-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]