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EAM-2201

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
EAM-2201
Legal status
Legal status
Identifiers
  • (4-Ethyl-1-naphthalenyl)[1-(5-fluoropentyl)-1H-indol-3-yl]-methanone
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H26FNO
Molar mass387.498 g·mol−1
3D model (JSmol)
  • CCC1=CC=C(C(C2=CN(CCCCCF)C3=C2C=CC=C3)=O)C4=C1C=CC=C4
  • InChI=1S/C26H26FNO/c1-2-19-14-15-23(21-11-5-4-10-20(19)21)26(29)24-18-28(17-9-3-8-16-27)25-13-7-6-12-22(24)25/h4-7,10-15,18H,2-3,8-9,16-17H2,1H3
  • Key:NSCXPXDWLZORPX-UHFFFAOYSA-N

EAM-2201 (4'-ethyl-AM-2201,5"-fluoro-JWH-210,SGT-14) is a drug that presumably acts as a potentagonist for thecannabinoid receptors.[2] It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient insynthetic cannabis smoking blends[3] Like the closely relatedMAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented bydesigner drug suppliers specifically forrecreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compoundsJWH-210 andAM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

Pharmacology

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EAM-2201 acts as afull agonist with abinding affinity of 0.380 nM atCB1 and 0.371 nM atCB2cannabinoid receptors.[4]

Legal status

[edit]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as EAM-2201 areSchedule I Controlled Substances.[5]

EAM-2201 was banned in New Zealand as atemporary class drug from 6 December 2012, after reports of addiction and psychosis associated with use of products containing EAM-2201 as an active ingredient, however this has been protested by some users who claim to have found medical benefits in the treatment of conditions such asphantom limb pain, since medicinal marijuana was not available in New Zealand andsynthetic cannabis products were used as a legal alternative.[6][7]

EAM-2201 is anAnlage II controlled drug in Germany.

As of October 2015 EAM-2201 is a controlled substance in China.[8]

Detection

[edit]

A forensic standard of EAM-2201 is available and commonly used inmass spectrometry.[9]

See also

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References

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  1. ^Anvisa (24 July 2023)."RDC Nº 804 – Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 25 July 2023).Archived from the original on 27 August 2023. Retrieved27 August 2023.
  2. ^Kim JH, Kim HS, Kong TY, Lee JY, Kim JY, In MK, Lee HS (February 2016). "In vitro metabolism of a novel synthetic cannabinoid, EAM-2201, in human liver microsomes and human recombinant cytochrome P450s".Journal of Pharmaceutical and Biomedical Analysis.119 (5):50–8.doi:10.1016/j.jpba.2015.11.023.PMID 26641707.
  3. ^Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (April 2013)."URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products".Forensic Science International.227 (1–3):21–32.doi:10.1016/j.forsciint.2012.08.047.PMID 23063179.
  4. ^Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016)."Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice".Forensic Toxicology.34 (2):329–343.doi:10.1007/s11419-016-0320-2.PMC 4929166.PMID 27429655.
  5. ^21 U.S.C. § 812:Schedules of controlled substances
  6. ^McNeilly H (1 October 2012)."I was possessed by a demon, says ex-legal high user".The New Zealand Herald.
  7. ^"Amputee: K2 'takes away my pain'".The New Zealand Herald. 28 November 2012.
  8. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
  9. ^"EAM-2201". Cayman Chemical. Retrieved21 July 2015.
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