BOB, also known as 4-bromo-2,5,ò-trimethoxyphenethylamine or as ò-methoxy-2C-B, is a psychedelic drug of the phenethylamine, 2C, and BOx families. It is the ò-methoxy derivative of 2C-B. BOB was first synthesized by Alexander Shulgin.
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.
BOB acts as a serotonin 5-HT<sub>2A</sub> receptor agonist. Its affinity (K<sub>i</sub>) 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.
The chemical synthesis of BOB has been described.
Analogues of BOB include BOH-2C-B (BOHB; ò-hydroxy-2C-B), òk-2C-B (ò-keto-2C-B), BOD (ò-methoxy-2C-D), BOHD (ò-hydroxy-2C-D), and ò-methyl-2C-B (BMB), among others.
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.
BOB is a controlled substance in Canada under phenethylamine blanket-ban language.
This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.
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.