BOB (psychedelic)

BOB, also known as 4-bromo-2,5,β-trimethoxyphenethylamine or as β-methoxy-2C-B, is a psychedelic drug of the phenethylamine, 2C, and BOx families.^[1] It is the β-methoxy derivative of 2C-B.^[1] BOB was first synthesized by Alexander Shulgin.^[1]

BOB

Clinical data
Other names	β-Methoxy-2C-B; 4-Bromo-2,5,β-trimethoxyphenethylamine; β-MeO-2C-D
Routes of administration	Oral[1]
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	10–20 hours[1]
Identifiers
IUPAC name 2-(4-bromo-2,5-dimethoxyphenyl)-2-methoxyethan-1-amine
CAS Number	98537-42-9 Y
PubChem CID	15185771
ChemSpider	21106261 Y
UNII	89A0HNR42S
ChEMBL	ChEMBL191051 Y
CompTox Dashboard (EPA)	DTXSID60569805
Chemical and physical data
Formula	C11H16BrNO3
Molar mass	290.157 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(c(cc1Br)OC)C(CN)OC
InChI InChI=1S/C11H16BrNO3/c1-14-9-5-8(12)10(15-2)4-7(9)11(6-13)16-3/h4-5,11H,6,13H2,1-3H3 Y Key:FYTLQNZPDWLGNU-UHFFFAOYSA-N Y
(verify)

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range as 10 to 20 mg orally and its duration as 10 to 20 hours.^[1] BOB produces an altered state of consciousness, tinnitus, a pleasant tingling throughout the body, and a sense of awareness.^[1]

Interactions

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

Pharmacology

Pharmacodynamics

BOB acts as a serotonin 5-HT_2A receptor agonist.^[2] Its affinity (K_i) was found to be 2.0 nM and its EC₅₀Tooltip half-maximal effective concentration was 0.12 nM with an E_maxTooltip maximal efficacy 63%.^[2] Its affinity was 20-fold lower than that of DOB, its activational potency was half that of DOB and its efficacy was slightly higher than that of DOB (63% and 38%, respectively).^[2] 2C-B was said to have comparable affinity as DOB.^[2]

Chemistry

Synthesis

The chemical synthesis of BOB has been described.^[1]

Analogues

Analogues of BOB include BOH-2C-B (β-hydroxy-2C-B), βk-2C-B (β-keto-2C-B), BOD (β-methoxy-2C-D), BOHD (β-hydroxy-2C-D), and β-methyl-2C-B, among others.^[1]

History

BOB was first described in the scientific literature by Alexander Shulgin, Peyton Jacob III, and Darrell Lemaire in 1985.^[3] Subsequently, it was described in greater detail by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).^[1] The drug's pharmacology was studied by Richard Glennon and colleagues in 2004.^[2]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.^[4]

See also

• BOx (psychedelics)
• 2C (psychedelics)