2C-B-AN

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
Drug class	Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Metabolites	2C-B
Duration of action	5–8 hours
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;

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]^[3] It is the derivative of 2C-B with a modified NBOMe-like N-(α′-cyanobenzyl) substitution.^[1]^[2]^[3] The drug is chemically unstable and has been found to be a prodrug of 2C-B in vivo.^[1]^[2]^[3] It is active at a dose of 50 mg orally and has a duration of 5 to 8 hours.^[1]^[2] 2C-B-AN has been described as producing stimulation and certain visual alterations.^[1] 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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 843–843. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
^ ^a ^b ^c ^d ^e ^f ^g ^h Elliott SP, Holdbrook T, Brandt SD (May 2020). "Prodrugs of New Psychoactive Substances (NPS): A New Challenge". Journal of Forensic Sciences. 65 (3): 913–920. doi:10.1111/1556-4029.14268. PMID 31943218.
^ ^a ^b ^c Ponce JD (2024). "The use of prodrugs as drugs of abuse". WIREs Forensic Science. 6 (3). doi:10.1002/wfs2.1514. ISSN 2573-9468. Retrieved 27 October 2025.

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