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 BOB's dose range as 10 to 20 mg orally and its duration as 10 to 20 hours.[1] The effects of BOB have been reported to include closed-eye visuals, a sense of awareness, a rich altered place, paranoia, feeling sociopathic, feeling indifferent or emotionless, irritability, neurological overstimulation and instability, tiredness, turmoil, body tingling, and tinnitus.[1]

Interactions

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

Canada

BOB is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[5]

United States

BOB is not an explicitly controlled substance in the United States.[6] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 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. 1 2 3 4 5 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. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  5. ↑ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Retrieved 12 March 2014.
  6. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
source: https://en.wikipedia.org/wiki/BOB_(psychedelic)