{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"LYDDINAZVHIBGP-UHFFFAOYSA-N","prefName":"EG-2201","symbol":"EG-2201","iupacName":"[9-(5-fluoropentyl)carbazol-3-yl]-naphthalen-1-ylmethanone","aliases":["EG2201","EG2201 RM","NA-5F-PCZMO","[9-(5-fluoropentyl)carbazol-3-yl]-naphthalen-1-ylmethanone"],"cas":null,"pubchemCid":"118796499","chebiId":null,"smiles":"C1=CC=C2C(=C1)C=CC=C2C(=O)C3=CC4=C(C=C3)N(C5=CC=CC=C54)CCCCCF","molecularFormula":"C28H24FNO","molecularWeight":409.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/118796499"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: EG-2201 belongs to synthetic chemistry alone, produced by acylation of an N-alkylated carbazole with a naphthoyl group. No source consulted describes its presence in a living organism.","originNote":"Entirely synthetic molecule: no source consulted describes it as a natural product, either in hemp or in any other organism. It has been identified as a constituent of Spice-type herbal blends sold on the illicit market (Schoeder et al., 2018), and its metabolites have been sought in the urine of users (Mogler et al., 2018).","discovered":""},"pharmacology":{"summaryFr":"EG-2201 is a synthetic cannabinoid with a carbazole core, from the same subclass as EG-018, bearing a 5-fluoropentyl chain. Schoeder et al. (2018) report an affinity of 22.4 nM at CB1 and 4.36 nM at CB2, and an activation of 94% at CB1 and 77% at CB2 relative to CP55,940. Mogler et al. (2018) describe its in vitro metabolism, marked by oxidative defluorination of the chain, and report only one case of consumption (n = 1) in their urine samples. No clinical study, case series or therapeutic indication is published in the sources consulted.","receptorSummaryFr":"Agonist at the CB1 and CB2 receptors. On human receptors expressed in CHO cells, Schoeder et al. (2018) measured an affinity of 22.4 nM at CB1 and 4.36 nM at CB2, by displacement of [3H]CP55,940. In a cyclic AMP accumulation assay, the molecule reaches 94% of the maximal effect of CP55,940 at CB1 (EC50 of 15.6 nM) and 77% at CB2 (EC50 of 5.65 nM). Schoeder et al. (2018) also tested the molecule on the orphan receptors GPR55 and GPR18 (beta-arrestin assay): it showed no measurable activity up to 10 µM.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":78,"reported":"Ki 22,4 nM (Schoeder et coll., 2018)","confidence":"medium"},{"target":"CB2","efficacy":"full_agonist","relativeActivity":89,"reported":"Ki 4,36 nM (Schoeder et coll., 2018)","confidence":"medium"}],"references":[{"label":"Schoeder et coll., affinités et efficacités CB1 et CB2 de constituants du Spice à noyaux indole, indazole, benzimidazole et carbazole, Forensic Toxicology, 2018","pmid":"29963207","doi":"10.1007/s11419-018-0415-z","url":"https://pubmed.ncbi.nlm.nih.gov/29963207/"},{"label":"Mogler et coll., métabolisme de phase I de l'EG-018, de l'EG-2201 et du MDMB-CHMCZCA dans les urines humaines, Drug Testing and Analysis, 2018","pmid":"29726116","doi":"10.1002/dta.2398","url":"https://pubmed.ncbi.nlm.nih.gov/29726116/"},{"label":"Potts et coll., classification et nomenclature des agonistes des récepteurs cannabinoïdes de synthèse, Clinical Toxicology, 2020","pmid":"31524007","doi":"10.1080/15563650.2019.1661425","url":"https://pubmed.ncbi.nlm.nih.gov/31524007/"},{"label":"Tang et coll., détection de l'EG-2201 par sonde fluorescente à transfert de charge, Analytical Methods, 2026","pmid":"42029041","doi":"10.1039/d6ay00189k","url":"https://pubmed.ncbi.nlm.nih.gov/42029041/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV : EG-018 nommé, EG-2201 absent ; familles génériques)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des conventions de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 118796499 (identifiants et masse moléculaire)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/118796499"}]},"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":10},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":15},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":10}],"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":"unscheduled","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 control measure at European Union level was identified in the sources consulted: control currently falls under the national legislation of member states. EG-2201 is also not listed in the INCB Green List 2026, which reproduces the substances of the 1971 conventions.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"EG-2201 is not named in the consolidated list of substances classified as narcotics, updated 16 February 2026. Its pentyl analogue, EG-018, is named instead in annex IV, under the order of 31 March 2017. Its structure does not meet the conditions of the generic families: the indol-3-yl methanone and indazol-3-yl methanone families require a carbonyl group carried by position 3 of an indole or indazole ring, whereas here the carbonyl is carried by the lateral benzene ring of the carbazole. The naphthoylpyrrole and naphthylmethylindole families do not apply either. The molecule is therefore not, at the date of this list, classified as a narcotic in France.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Schoeder et coll., affinités et efficacités CB1 et CB2 de constituants du Spice à noyaux indole, indazole, benzimidazole et carbazole, Forensic Toxicology, 2018","pmid":"29963207","doi":"10.1007/s11419-018-0415-z","url":"https://pubmed.ncbi.nlm.nih.gov/29963207/"},{"label":"Mogler et coll., métabolisme de phase I de l'EG-018, de l'EG-2201 et du MDMB-CHMCZCA dans les urines humaines, Drug Testing and Analysis, 2018","pmid":"29726116","doi":"10.1002/dta.2398","url":"https://pubmed.ncbi.nlm.nih.gov/29726116/"},{"label":"Potts et coll., classification et nomenclature des agonistes des récepteurs cannabinoïdes de synthèse, Clinical Toxicology, 2020","pmid":"31524007","doi":"10.1080/15563650.2019.1661425","url":"https://pubmed.ncbi.nlm.nih.gov/31524007/"},{"label":"Tang et coll., détection de l'EG-2201 par sonde fluorescente à transfert de charge, Analytical Methods, 2026","pmid":"42029041","doi":"10.1039/d6ay00189k","url":"https://pubmed.ncbi.nlm.nih.gov/42029041/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe IV : EG-018 nommé, EG-2201 absent ; familles génériques)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (substances des conventions de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 118796499 (identifiants et masse moléculaire)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/118796499"}],"meta":{"slug":"eg-2201","url":"https://en.phytogrammes.com/wiki/eg-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."}}