BOB (psychedelic)

BOB
Clinical data
Other namesβ-Methoxy-2C-B; 4-Bromo-2,5,β-trimethoxyphenethylamine; β-MeO-2C-D
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action10–20 hours[1]
Identifiers
  • 2-(4-bromo-2,5-dimethoxyphenyl)-2-methoxyethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H16BrNO3
Molar mass290.157 g·mol−1
3D model (JSmol)
  • COc1cc(c(cc1Br)OC)C(CN)OC
  • 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)

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]

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-HT2A receptor agonist.[2] Its affinity (Ki) was found to be 2.0 nM and its EC50Tooltip half-maximal effective concentration was 0.12 nM with an EmaxTooltip 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 (BOHB; 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 (BMB), 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

United Kingdom

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

See also

References

  1. ^ a b c d e f g h i j Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. BOB Entry
  2. ^ a b c d e Glennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem. 47 (24): 6034–6041. doi:10.1021/jm040082s. PMID 15537358.
  3. ^ Lemaire D, Jacob P, Shulgin AT (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". J Pharm Pharmacol. 37 (8): 575–577. doi:10.1111/j.2042-7158.1985.tb03072.x. PMID 2864422.
  4. ^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.
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