2C-B-AN

2C-B-AN, also known as 4-bromo-N-(α′-cyanobenzyl)-2,5-dimethoxyphenethylamine or as brolphetaminil, is a psychedelic drug of the phenethylamine, 2C, and N-benzylphenethylamine families related to 2C-B.^[1][2][4] It is the derivative of 2C-B with a modified NBOMe-like N-(α′-cyanobenzyl) substitution.^[1][2][4] The drug is chemically unstable and has been found to be a prodrug of 2C-B in vivo.^[1][2][4] It is active at a dose of 50 mg orally and has a duration of 5 to 8 hours.^[1][2][3] However, a wider dose range of 30 to 100 mg or more has also been reported.^[3] 2C-B-AN has been described as producing stimulation and certain visual alterations.^[1][3] It was described in the scientific literature by Daniel Trachsel in 2013, who cited personal communication with P. Rausch in 2009 as the source for the information.^[1] 2C-B-AN was encountered as a novel designer drug in Europe by 2016.^[2][3] It may be a controlled substance in Canada under phenethylamine blanket-ban language.^[5] The drug is not an explicitly controlled substance in the United States.^[6]

Other names2CB-AN; 2C-B-Aminonitrile; Brolphetaminil; 4-Bromo-N-(α′-cyanobenzyl)-2,5-dimethoxyphenethylamine; 4-Bromo-N-(cyano(phenyl)methyl)-2,5-dimethoxyphenethylamine

Routes of
administrationOral^[1][2][3]

Drug classSerotonin 5-HT₂ receptor agonist; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

ATC code

• None

Quick facts Clinical data, Other names ...

2C-B-AN

Clinical data
Other names	2CB-AN; 2C-B-Aminonitrile; Brolphetaminil; 4-Bromo-N-(α′-cyanobenzyl)-2,5-dimethoxyphenethylamine; 4-Bromo-N-(cyano(phenyl)methyl)-2,5-dimethoxyphenethylamine
Routes of administration	Oral[1][2][3]
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Metabolites	2C-B[2][3]
Onset of action	1 hour[3]
Duration of action	5–8 hours[1][2][3]
Identifiers
IUPAC name 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethylamino]-2-phenylacetonitrile
PubChem CID	165412129
UNII	F6VF6U8BHV
Chemical and physical data
Formula	C18H19BrN2O2
Molar mass	375.266 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCNC(C#N)C2=CC=CC=C2)OC)Br
InChI InChI=1S/C18H19BrN2O2/c1-22-17-11-15(19)18(23-2)10-14(17)8-9-21-16(12-20)13-6-4-3-5-7-13/h3-7,10-11,16,21H,8-9H2,1-2H3 Key:ZQUGFGBAFZUJFB-UHFFFAOYSA-N

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