BOB (psychedelic)

Use and effects

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

Interactions

Pharmacology

Pharmacodynamics

BOB acts as a serotonin 5-HT2A receptor agonist. Its affinity (Ki) was found to be 2.0nM and its was 0.12nM with an 63%. 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). 2C-B was said to have comparable affinity as DOB.

Chemistry

Synthesis

The chemical synthesis of BOB has been described.

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.

History

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

Society and culture

Legal status

Canada

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

United Kingdom

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

United States

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

References

References

1. {{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal013.shtml BOB Entry]
2. (August 1985). "Ring-substituted beta-methoxyphenethylamines: a new class of psychotomimetic agents active in man". J Pharm Pharmacol.
3. (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem.
4. "Controlled Drugs and Substances Act".
5. "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design.
6. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.