BOB (psychedelic)
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| 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 |
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| Duration of action | 10–20 hours[1] |
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| Formula | C11H16BrNO3 |
| Molar mass | 290.157 g·mol−1 |
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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
Pharmacology
Pharmacodynamics
BOB acts as a serotonin 5-HT2A receptor agonist.[2] Its affinity (Ki) was found to be 2.0 nM and its EC50 was 0.12 nM with an Emax 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
Legal status
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.