N-Ethyl-2C-B

N-Ethyl-2C-B, also known as 2C-B-E, is a psychedelic drug of the phenethylamine and 2C families related to 2C-B.^[1]^[2] It is the N-ethyl derivative of 2C-B.^[1]^[2]

Other names2C-B-E; 2C-BE; 4-Bromo-N-ethyl-2,5-dimethoxyphenethylamine

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

Legal status

In general unscheduled

CAS Number

155639-24-0^Y

Quick facts Clinical data, Other names ...

N-Ethyl-2C-B
Clinical data


Other names	2C-B-E; 2C-BE; 4-Bromo-N-ethyl-2,5-dimethoxyphenethylamine
Drug class	Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	In general unscheduled
Identifiers
IUPAC name 2-(4-bromo-2,5-dimethoxyphenyl)-N-ethylethanamine
CAS Number	155639-24-0^Y
PubChem CID	10379339
ChemSpider	8554782
UNII	JC6CK9H75Z
ChEMBL	ChEMBL57147
CompTox Dashboard (EPA)	DTXSID601336903
Chemical and physical data
Formula	C₁₂H₁₈BrNO₂
Molar mass	288.185 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC(CCNCC)=C(OC)C=C1Br
InChI InChI=1S/C12H18BrNO2/c1-4-14-6-5-9-7-12(16-3)10(13)8-11(9)15-2/h7-8,14H,4-6H2,1-3H3 Key:FTXAZQUDSNEXMB-UHFFFAOYSA-N

The drug shows affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 40–330 nM and 1,930 nM, respectively).^[3]^[1] Its affinities for these receptors were 10–40-fold and 54-fold lower than those of 2C-B, respectively.^[3]^[4] N-Ethyl-2C-B has been reported to be a potent full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 3.39 nM and an E_maxTooltip maximal efficacy of 106%^[5] It was 8-fold more potent as a serotonin 5-HT_2A receptor agonist in vitro than LSD in the same study.^[5]

The chemical synthesis of N-ethyl-2C-B has been described.^[3] Analogues of N-ethyl-2C-B include 2C-B, N-methyl-2C-B, N-methyl-2C-I, N-methyl-DOB, N-benzyl-2C-B, and 25B-NBOMe, among others.^[1]^[6]^[4]

N-Ethyl-2C-B was first described in the scientific literature by Richard Glennon and colleagues by 1994.^[3] It was encountered as a novel designer drug in Finland in 2007.^[7]^[8]^[9]^[10] The drug is a controlled substance in Finland.^[11] In addition, it is a controlled substance in Canada under phenethylamine blanket-ban language.^[12]

References

[1]
Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
[2]
AIPSIN. "2C-B-E (N-etyl-2C-B)". АИПСИН (in Russian). Retrieved 1 January 2026.
[3]
Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID 8027974.
[4]
Papoutsis I, Nikolaou P, Stefanidou M, Spiliopoulou C, Athanaselis S (2015). "25B-NBOMe and its precursor 2C-B: modern trends and hidden dangers". Forensic Toxicology. 33 (1): 1–11. doi:10.1007/s11419-014-0242-9. ISSN 1860-8965. Nowadays, 2C-B, although a controlled substance worldwide, remains popular among young people who use it in dance clubs and at rave parties [14]. Moreover, new N-substituted derivatives of it have emerged on the drug abuse market. The use or possession and supply of these derivatives remains legal until national or international drug laws prohibit them. The simplest among them are the alkyl derivatives; N-methyl2C-B, N,N-dimethyl-2C-B, and N-ethyl-2C-B. However, these substances are considerably less potent than 2C-B, with affinities for the 5-HT2A receptor being up to 40 times lower [5].
[5]
Stalberga D, Kronstrand R, Schranz B, van Zijl N, Karlman S, Aref S, et al. (July 2026). "Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5-HT2A receptor". Br J Pharmacol. doi:10.1111/bph.70587. PMID 42449077.
[6]
Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
[7]
"2007 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) & Europol.
[8]
King LA (2014). "New phenethylamines in Europe". Drug Testing and Analysis. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
[9]
Schifano F, Orsolini L, Papanti D, Corkery J (2017). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. PMID 27272067. Other popular compounds of this class include 2C-D (2,5-dimethoxy-4-methylphenethylamine), 2C-E (2,5-dimethoxy-4-ethylphenethylamine), 2C-N (2,5-dimethoxy-4-nitrophenethylamine), 2C-H (2,5-dimethoxyphenethylamine), and N-ethyl-2C-B (N-ethyl-2C-B) [2].
[10]
Corkery JM, Orsolini L, Papanti D, Schifano F (2018). "CHAPTER 8. Novel Psychoactive Substances (NPS) and Recent Scenarios: Epidemiological, Anthropological and Clinical Pharmacological Issues". Comprehensive Series in Photochemical & Photobiological Sciences. Cambridge: Royal Society of Chemistry. pp. 207–256. doi:10.1039/9781788010344-00207. ISBN 978-1-78262-768-5. The first and the most common compound of this group is the 2-CB (aka 'Nexus'/'Venus'/'Bees'/'Bromo Mescaline'/'Toonies'/-'Bromo'/ 'Erox'/'Synergy'/'XTC'). After its scheduling by the Drug Enforcement Agency (DEA) in 1995, a large range of new 2C compounds were synthesised and marketed, such as 2C-D, 2C-E, 2C-B, 2C-N, 2C-H, N-ethyl-2C-B, etc. 6
[11]
"Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government Decree on Psychoactive Substances Banned from the Consumer Market]. Finlex Data Bank (in Finnish).
[12]
"Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

See also

References

External links

Related Articles