BOH-2C-B

BOH-2C-B, or BOHB, also known as 4-bromo-2,5-dimethoxy-β-hydroxyphenethylamine or as β-hydroxy-2C-B, is a psychedelic drug of the phenethylamine, 2C, and BOx families.^[2] It is the β-hydroxy derivative of 2C-B.^[2] The drug has been encountered as a novel designer drug.^[3][4]

BOH-2C-B

Clinical data
Other names	BOH-2C-B-; BOHB; β-Hydroxy-4-bromo-2,5-dimethoxyphenethylamine; β-Hydroxy-2C-B; β-OH-2C-B
Routes of administration	Oral[1]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in Netherlands
Pharmacokinetic data
Onset of action	Unknown[1]
Duration of action	Unknown[1]
Identifiers
IUPAC name 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-ol
CAS Number	677277-62-2
PubChem CID	11370394
ChemSpider	9545311
UNII	W6KJ195I24
ChEMBL	ChEMBL191050
CompTox Dashboard (EPA)	DTXSID101342414
Chemical and physical data
Formula	C10H14BrNO3
Molar mass	276.130 g·mol−1
3D model (JSmol)	Interactive image
SMILES NCC(c1cc(OC)c(cc1OC)Br)O
InChI InChI=1S/C10H14BrNO3/c1-14-9-4-7(11)10(15-2)3-6(9)8(13)5-12/h3-4,8,13H,5,12H2,1-2H3 Key:PCSKDXWCLQXURQ-UHFFFAOYSA-N

Use and effects

BOH-2C-B was not included or mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).^[5] Subsequently, Daniel Trachsel listed BOHB's dose as 30 mg or more orally in his book Phenethylamine: von der Struktur zur Funktion (Phenethylamines: From Structure to Function).^[1]

Interactions

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

Pharmacology

Pharmacodynamics

BOH-2C-B acts as a serotonin 5-HT_2A receptor agonist.^[2][4]

Chemistry

BOH-2C-B is a substituted phenethylamine.^[2] It features methoxy substituents at the 2- and 5-position of the ring, as well as a bromine at the 4-position.^[2] A hydroxy group is present at the beta (β) position from the functional amine group connected to the alpha (α) carbon, giving rise to its name.^[2]

Analogues

Analogues of BOH-2C-B include 2C-B, BOB (β-methoxy-2C-B), βk-2C-B (β-keto-2C-B), β-methyl-2C-B, BOHD (β-hydroxy-2C-D), and BOD (β-methoxy-2C-D), among others.^[5]

History

BOH-2C-B was first described in a 2004 study by Richard Glennon and colleagues on β-oxygenated 5-HT_2A serotonin receptor agonists, although it is not mentioned by name.^[2] It was encountered as a novel designer drug in 2019.^[3][4] However, it is said to have been on the market since 2015.^[4]

Society and culture

Legal status

BOH-2C-B is a controlled substance in the following countries:

• Germany: BOH-2C-B is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Possession is illegal but not penalized.^[6]
• Netherlands:: BOH-2C-B is not specifically scheduled in the NL but may be considered a ring-derived analogue of 2-phenethylamine which would make it illegal under updates made to the Dutch Opium Act in February 2024.^[7]
• United Kingdom: BOH-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.^[8]
• United States: BOH-2C-B is unscheduled in the U.S., but may be considered an analogue of 2C-B under the Federal Analogue Act, and thus a Schedule I drug.^[9]

See also

• BOx (psychedelics)
• 2C (psychedelics)