Chemistry:N-Ethyl-2C-B

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Short description: Chemical compound

N-Ethyl-2C-B
File:N-Ethyl-2C-B.svg
Clinical data
Other names2C-B-E; 2C-BE; 4-Bromo-N-ethyl-2,5-dimethoxyphenethylamine
Drug classSerotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • In general unscheduled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC12H18BrNO2
Molar mass288.185 g·mol−1
3D model (JSmol)

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]

The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 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-HT2A receptor, with an EC50 of 3.39 nM and an Emax of 106%[5] It was 8-fold more potent as a serotonin 5-HT2A 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]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. 
  2. ↑ 2.0 2.1 AIPSIN. "2C-B-E (N-etyl-2C-B)" (in ru). https://aipsin.com/newsubstance/1022/. 
  3. ↑ 3.0 3.1 3.2 3.3 "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry 37 (13): 1929–1935. June 1994. doi:10.1021/jm00039a004. PMID 8027974. 
  4. ↑ 4.0 4.1 "25B-NBOMe and its precursor 2C-B: modern trends and hidden dangers". Forensic Toxicology 33 (1): 1–11. 2015. 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. ↑ 5.0 5.1 "Comprehensive in vitro profiling of traditional and emerging stimulants at monoamine transporters and the 5-HT2A receptor". Br J Pharmacol. July 2026. doi:10.1111/bph.70587. PMID 42449077. 
  6. ↑ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. 
  7. ↑ "2007 Annual Report on the implementation of Council Decision 2005/387/JHA". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) & Europol. https://www.emcdda.europa.eu/system/files/publications/503/2007_Implementation_report_281403.pdf. 
  8. ↑ "New phenethylamines in Europe". Drug Testing and Analysis 6 (7–8): 808–818. 2014. doi:10.1002/dta.1570. PMID 24574327. 
  9. ↑ "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. 2017. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. "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. ↑ "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. 2018. 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" (in Finnish). Finlex Data Bank. https://finlex.fi/fi/lainsaadanto/2014/1130. 
  12. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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