{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"NSCXPXDWLZORPX-UHFFFAOYSA-N","prefName":"EAM-2201","symbol":"EAM-2201","iupacName":"(4-ethylnaphthalen-1-yl)-[1-(5-fluoropentyl)indol-3-yl]methanone","aliases":["4'-Ethyl-AM-2201","(4-ETHYLNAPHTHYL)-AM-2201","5-fluoro-JWH-210","JWH-210 N-(5-FLUOROPENTYL)"],"cas":"1364933-60-7","pubchemCid":"71308187","chebiId":null,"smiles":"CCC1=CC=C(C2=CC=CC=C12)C(=O)C3=CN(C4=CC=CC=C43)CCCCCF","molecularFormula":"C26H26FNO","molecularWeight":387.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/71308187"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway is reported: EAM-2201 is not reported from any hemp chemotype or living organism. It belongs to chemical synthesis alone, within the naphthoylindole class.","originNote":"Synthetic molecule: no natural occurrence is reported in the sources consulted. It has been found in illicit products, notably in Japan, where Uchiyama et al. (2013) list it among twelve newly distributed cannabimimetic compounds.","discovered":""},"pharmacology":{"summaryFr":"EAM-2201 is a synthetic cannabinoid of the naphthoylindole family, the 5-fluorinated analogue of JWH-210. In the study by Marusich et al. (2018), its affinity is 0.41 nM at CB1 and 0.38 nM at CB2, and its maximal stimulation of CB1 exceeds that of CP55,940 (270.3% against 163.3% above basal); Costain et al. (2016) rank it among the full CB1 agonists. In mice, it substitutes for THC in a discrimination task with an ED50 of 0.04 µmol/kg, the most potent of the batch tested, although its dose-response curve is not monotonic. Human data are limited to forensic observations: a death from diabetic ketoacidosis in which eleven synthetic cannabinoids, including EAM-2201, were detected in blood (Hess et al., 2015), and a fatal case of intoxication by a mixture combining EAM-2201 with two other synthetic cannabinoids and α-PVP (Yamagishi et al., 2018). No therapeutic use is documented in the sources consulted, and no controlled clinical trial has been published in them.","receptorSummaryFr":"Agonist at the CB1 and CB2 receptors. In the study by Marusich et al. (2018), which also measures CP55,940, the affinity at CB1 is 0.41 nM (standard error 0.04), against 1.15 nM for CP55,940. At CB1, [35S]GTPγS stimulation gives an EC50 of 46.8 nM and a maximal efficacy of 270.3% above basal, against 163.3% for CP55,940. At CB2, the affinity is 0.38 nM (standard error 0.05) and the maximal efficacy remains lower, at 40.2%, against 55.1% for CP55,940. Costain et al. (2016) rank it among the full CB1 agonists tested in HEK293T cells. No measured effect on another target is reported in the sources consulted.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":95,"reported":"Ki 0,41 ± 0,04 nM (Marusich et coll., 2018) ; CE50 46,8 nM en [35S]GTPγS","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":95,"reported":"Ki 0,38 ± 0,05 nM (Marusich et coll., 2018) ; efficacité maximale de 40,2 % en [35S]GTPγS, contre 55,1 % pour le CP55,940","confidence":"medium"}],"references":[{"label":"Marusich et coll., Neuropharmacology, 2018 : affinités CB1 et CB2, activation de la [35S]GTPγS et substitution au THC pour l'EAM-2201 (tableau 1)","pmid":"29113898","doi":"10.1016/j.neuropharm.2017.10.041","url":"https://pubmed.ncbi.nlm.nih.gov/29113898/"},{"label":"Costain et coll., Eur J Pharmacol, 2016 : caractérisation pharmacologique des cannabinoïdes de synthèse émergents dans des cellules HEK293T","pmid":"27260125","doi":"10.1016/j.ejphar.2016.05.040","url":"https://pubmed.ncbi.nlm.nih.gov/27260125/"},{"label":"Cannaert et coll., Analytical Chemistry, 2016 : activité des cannabinoïdes de synthèse et de leurs métabolites dans un test de bioactivité, dont l'EAM-2201","pmid":"27779402","doi":"10.1021/acs.analchem.6b02600","url":"https://pubmed.ncbi.nlm.nih.gov/27779402/"},{"label":"Kim et coll., J Pharm Biomed Anal, 2016 : métabolisme in vitro de l'EAM-2201 sur microsomes hépatiques humains et CYP recombinants","pmid":"26641707","doi":"10.1016/j.jpba.2015.11.023","url":"https://pubmed.ncbi.nlm.nih.gov/26641707/"},{"label":"Kong et coll., Molecules, 2018 : inhibition in vitro des CYP et des UGT par l'EAM-2201 sur microsomes hépatiques humains","pmid":"29659506","doi":"10.3390/molecules23040920","url":"https://pubmed.ncbi.nlm.nih.gov/29659506/"},{"label":"Yamagishi et coll., Legal Medicine, 2018 : cas mortel associant EAM-2201, AB-PINACA, AB-FUBINACA et α-PVP, avec dosages sanguins et tissulaires","pmid":"30268690","doi":"10.1016/j.legalmed.2018.08.004","url":"https://pubmed.ncbi.nlm.nih.gov/30268690/"},{"label":"Hess et coll., Forensic Science International, 2015 : décès par cétoacidose diabétique et cannabinoïdes de synthèse","pmid":"26363623","doi":"10.1016/j.forsciint.2015.08.012","url":"https://pubmed.ncbi.nlm.nih.gov/26363623/"},{"label":"Uchiyama et coll., Forensic Science International, 2013 : douze cannabimimétiques détectés dans des produits illicites au Japon, dont l'EAM-2201","pmid":"23063179","doi":"10.1016/j.forsciint.2012.08.047","url":"https://pubmed.ncbi.nlm.nih.gov/23063179/"},{"label":"Kakehashi et coll., Forensic Science International, 2020 : concentrations sanguines et urinaires de cannabinoïdes de synthèse chez des conducteurs impliqués dans des accidents","pmid":"31902661","doi":"10.1016/j.forsciint.2019.110106","url":"https://pubmed.ncbi.nlm.nih.gov/31902661/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, famille des indol-3-yl méthanones","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Liste verte 2026 des substances sous contrôle international (tableaux de la convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 71308187 (EAM-2201) : formule, masse moléculaire moyenne et InChIKey","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/71308187"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"profile":[{"key":"calm","label":"Calm","description":"Relaxation of body and mind; reduced mental noise without marked drowsiness.","intensity":5},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":5},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":8},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":8},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":8}],"doseRanges":null,"humanDataCharacterised":false},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":true,"bannerTextFr":"Aucune dose humaine caractérisée : données animales / in vitro uniquement. Profil d'effet, marge de sécurité et toxicité aiguë non documentés en clinique humaine.","toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"Unscheduled","frScheduleStatus":"controlled-clause","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"No harmonised European Union control measure has been identified in the sources consulted, so control rests on national law. At international level, EAM-2201 is not on the INCB green list for 2026, which reproduces the schedules of the 1971 Convention.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"A narcotic in France, by generic clause and not by name. EAM-2201 is not named in the consolidated list of narcotics published by the ANSM, updated to 16 February 2026. It falls under the indol-3-yl methanone family of annex IV of the ANSM consolidated list, which covers any molecule bearing on the indole nitrogen an alkyl or haloalkyl substituent, and on the carbon of the methanone bridge a naphthyl group, substituted or not. EAM-2201 meets both conditions point by point: a fluorinated pentyl chain on the nitrogen, and a naphthyl bearing an ethyl group on the methanone bridge. JWH-210, from which it differs only by that fluorine, is named in the same annex. This molecule has no place in the CBD trade.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Marusich et coll., Neuropharmacology, 2018 : affinités CB1 et CB2, activation de la [35S]GTPγS et substitution au THC pour l'EAM-2201 (tableau 1)","pmid":"29113898","doi":"10.1016/j.neuropharm.2017.10.041","url":"https://pubmed.ncbi.nlm.nih.gov/29113898/"},{"label":"Costain et coll., Eur J Pharmacol, 2016 : caractérisation pharmacologique des cannabinoïdes de synthèse émergents dans des cellules HEK293T","pmid":"27260125","doi":"10.1016/j.ejphar.2016.05.040","url":"https://pubmed.ncbi.nlm.nih.gov/27260125/"},{"label":"Cannaert et coll., Analytical Chemistry, 2016 : activité des cannabinoïdes de synthèse et de leurs métabolites dans un test de bioactivité, dont l'EAM-2201","pmid":"27779402","doi":"10.1021/acs.analchem.6b02600","url":"https://pubmed.ncbi.nlm.nih.gov/27779402/"},{"label":"Kim et coll., J Pharm Biomed Anal, 2016 : métabolisme in vitro de l'EAM-2201 sur microsomes hépatiques humains et CYP recombinants","pmid":"26641707","doi":"10.1016/j.jpba.2015.11.023","url":"https://pubmed.ncbi.nlm.nih.gov/26641707/"},{"label":"Kong et coll., Molecules, 2018 : inhibition in vitro des CYP et des UGT par l'EAM-2201 sur microsomes hépatiques humains","pmid":"29659506","doi":"10.3390/molecules23040920","url":"https://pubmed.ncbi.nlm.nih.gov/29659506/"},{"label":"Yamagishi et coll., Legal Medicine, 2018 : cas mortel associant EAM-2201, AB-PINACA, AB-FUBINACA et α-PVP, avec dosages sanguins et tissulaires","pmid":"30268690","doi":"10.1016/j.legalmed.2018.08.004","url":"https://pubmed.ncbi.nlm.nih.gov/30268690/"},{"label":"Hess et coll., Forensic Science International, 2015 : décès par cétoacidose diabétique et cannabinoïdes de synthèse","pmid":"26363623","doi":"10.1016/j.forsciint.2015.08.012","url":"https://pubmed.ncbi.nlm.nih.gov/26363623/"},{"label":"Uchiyama et coll., Forensic Science International, 2013 : douze cannabimimétiques détectés dans des produits illicites au Japon, dont l'EAM-2201","pmid":"23063179","doi":"10.1016/j.forsciint.2012.08.047","url":"https://pubmed.ncbi.nlm.nih.gov/23063179/"},{"label":"Kakehashi et coll., Forensic Science International, 2020 : concentrations sanguines et urinaires de cannabinoïdes de synthèse chez des conducteurs impliqués dans des accidents","pmid":"31902661","doi":"10.1016/j.forsciint.2019.110106","url":"https://pubmed.ncbi.nlm.nih.gov/31902661/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, famille des indol-3-yl méthanones","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Liste verte 2026 des substances sous contrôle international (tableaux de la convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 71308187 (EAM-2201) : formule, masse moléculaire moyenne et InChIKey","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/71308187"}],"meta":{"slug":"eam-2201","url":"https://en.phytogrammes.com/wiki/eam-2201","lastVerified":"2026-05-01","dataUpdatedAt":"2026-10-13","confidence":"high","dataCompletenessPct":90,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}