EAM-2201

{{Short description|Chemical compound}}

{{Use dmy dates|date=December 2024}}

{{Infobox drug

| IUPAC_name = (4-Ethyl-1-naphthalenyl)[1-(5-fluoropentyl)-1H-indol-3-yl]-methanone

| image = EAM-2201_structure.png

| width = 150

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 – Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule II

| legal_UK = PSA

| legal_US = Schedule I

| legal_DE = Anlage II

| legal_NZ = Temporary Class

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 1364933-60-7

| ATC_prefix =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = OO52S1U9ET

| ATC_suffix =

| PubChem = 71308187

| ChemSpiderID = 29341514

| C=26 | H=26 | F=1 | N=1 | O=1

| smiles = CCC1=CC=C(C(C2=CN(CCCCCF)C3=C2C=CC=C3)=O)C4=C1C=CC=C4

| StdInChI = 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

| StdInChIKey = NSCXPXDWLZORPX-UHFFFAOYSA-N

}}

EAM-2201 (4'-ethyl-AM-2201, 5"-fluoro-JWH-210, SGT-14) is a drug that presumably acts as a potent agonist for the cannabinoid receptors.{{cite journal | vauthors = Kim JH, Kim HS, Kong TY, Lee JY, Kim JY, In MK, Lee HS | title = In vitro metabolism of a novel synthetic cannabinoid, EAM-2201, in human liver microsomes and human recombinant cytochrome P450s | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 119 | issue = 5 | pages = 50–8 | date = February 2016 | pmid = 26641707 | doi = 10.1016/j.jpba.2015.11.023 }} 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 in synthetic cannabis smoking blends{{cite journal | vauthors = Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y | title = URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products | journal = Forensic Science International | volume = 227 | issue = 1–3 | pages = 21–32 | date = April 2013 | pmid = 23063179 | doi = 10.1016/j.forsciint.2012.08.047 | url = http://www.fsijournal.org/article/S0379-0738%2812%2900434-3/abstract | url-access = subscription }} Like the closely related MAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by designer drug suppliers specifically for recreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds JWH-210 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.