4C-B

4C-B, also known as 4C-DOB or DOB-B, as well as 4-bromo-2,5-dimethoxy-α-ethylphenethylamine, is a lesser-known psychedelic drug of the phenethylamine, phenylisobutylamine, and 4C families related to 2C-B (the 2C analogue) and DOB (the DOx analogue).^[2] It is a reasonably potent 5-HT_2A receptor partial agonist with a K_i of 7.6 nM, but has relatively low efficacy (15% relative to 5-HT).^[3] It is briefly mentioned in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known And Loved), but was never tested by Shulgin.^[4] Subsequently, the drug was tested by Daniel Trachsel and colleagues, and was found to be active in a dose range of 50 to 80 mg with a duration of around 8 hours.^[1] It produced pronounced psychedelic effects, though with generally milder effects than 2C-B or DOB.^[1]

4C-B

Clinical data
Other names	4C-DOB; DOB-B; 4-Bromo-2,5-dimethoxy-α-ethylphenethylamine
Routes of administration	Oral[1]
Drug class	Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	~8 hours[1]
Identifiers
IUPAC name 1-(4-bromo-2,5-dimethoxyphenyl)butan-2-amine
CAS Number	69294-23-1
PubChem CID	12140147
ChemSpider	23256805
ChEMBL	ChEMBL365711
CompTox Dashboard (EPA)	DTXSID101336665
Chemical and physical data
Formula	C12H18BrNO2
Molar mass	288.185 g·mol−1
3D model (JSmol)	Interactive image
Melting point	204 to 206 °C (399 to 403 °F)
SMILES CCC(CC1=CC(=C(C=C1OC)Br)OC)N
InChI InChI=1S/C12H18BrNO2/c1-4-9(14)5-8-6-12(16-3)10(13)7-11(8)15-2/h6-7,9H,4-5,14H2,1-3H3 Key:QQPRORAZQWLMTQ-UHFFFAOYSA-N

See also

• 4C (psychedelics)
• 4C-T-2
• Ariadne (psychedelic) (4C-D)
• ZC-B