BOx (psychedelics)

Not to be confused with Benzoxepin or TFMBOX.

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]

BOD (β-hydroxy-2C-D), a BOx psychedelic.^[1][2]

Certain BOx drugs like BOB (β-methoxy-2C-B) have been found to act as serotonin 5-HT_2A 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

Oral doses, durations, and effects of BOx drugs

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]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Related compounds

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

• Substituted methoxyphenethylamine