{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"FJMMDJDPNLZYLA-UHFFFAOYSA-N","prefName":"EG-018","symbol":"EG-018","iupacName":"naphthalen-1-yl-(9-pentylcarbazol-3-yl)methanone","aliases":["naphthalen-1-yl(9-pentyl-9H-carbazol-3-yl)methanone","1-naphthyl-(9-pentylcarbazol-3-yl)methanone"],"cas":null,"pubchemCid":"118796466","chebiId":null,"smiles":"CCCCCN1C2=C(C=C(C=C2)C(=O)C3=CC=CC4=CC=CC=C43)C5=CC=CC=C51","molecularFormula":"C28H25NO","molecularWeight":391.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/118796466"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic route: the molecule is produced by no living organism. It belongs to synthetic chemistry alone: it is a diaryl ketone linking an N-pentylated carbazole core to a naphthyl group through a carbonyl bond.","originNote":"Synthetic molecule, described as such in the sources consulted, with no known link to hemp. The sources consulted do not document the publication of its initial synthesis or its author. It was first identified in the United Kingdom between February 2013 and January 2015, then detected in Japan and the United States (Gamage et al., 2020). It is sold online and has been detected in illicit products and in human samples.","discovered":""},"pharmacology":{"summaryFr":"EG-018 belongs to the carbazoles, a subgroup of synthetic cannabinoids whose carbazole core carries a naphthoyl group and a pentyl chain. Gamage et al. (2020) measured an affinity of 21.8 nM for CB1 and 7.76 nM for CB2, with weak partial activation in [35S]GTPγS binding, an efficacy of about 28% of that of CP55,940 at CB1. In mice, no tetrad effect was observed up to 100 mg/kg given intraperitoneally. An intravenous dose of 56 mg/kg, however, caused hypomotility, catalepsy and hypothermia, the catalepsy being blocked by rimonabant. Its main urinary metabolites were described in 2018 (Mogler et al., 2018). Human data are limited to anecdotal reports and toxicological detections (Gamage et al., 2020).","receptorSummaryFr":"A partial agonist at the CB1 and CB2 receptors, with nanomolar affinity: Ki of 21.8 nM at CB1 and 7.76 nM at CB2, about three times stronger at CB2 (Gamage et al., 2020). Unlike most synthetic agonists, it activates G proteins only weakly: in [35S]GTPγS binding, its efficacy reaches about 28% of that of CP55,940 at CB1 and 40% at CB2, with an EC50 of 37.1 nM at CB1. It is therefore less efficacious than THC at CB1, but more potent in this assay. A later study describes it as a low-efficacy agonist (Finlay et al., 2022). Among 21 synthetic agonists compared, it is the only one showing a preference of about tenfold for G-protein signalling over β-arrestin 2 recruitment (Wouters et al., 2020). In a functional AequoScreen test on CHO-K1 cells, it was inactive (Bäckberg et al., 2023), a result that contrasts with the partial activity described by Gamage et al. (2020).","binding":[{"target":"CB1","efficacy":"partial_agonist","relativeActivity":78,"reported":"Ki 21,8 nM (Gamage et coll., 2020)","confidence":"medium"},{"target":"CB2","efficacy":"partial_agonist","relativeActivity":86,"reported":"Ki 7,76 nM (Gamage et coll., 2020)","confidence":"medium"}],"references":[{"label":"Gamage et coll., évaluation in vitro et in vivo de l'EG-018, Pharmacology Biochemistry and Behavior, 2020","pmid":"32247816","doi":"10.1016/j.pbb.2020.172918","url":"https://pubmed.ncbi.nlm.nih.gov/32247816/"},{"label":"Finlay et coll., déterminants de l'efficacité agoniste au récepteur CB1, analogues de l'EG-018, Pharmacology Research and Perspectives, 2022","pmid":"35041297","doi":"10.1002/prp2.901","url":"https://pubmed.ncbi.nlm.nih.gov/35041297/"},{"label":"Mogler et coll., métabolisme de phase I de l'EG-018, de l'EG-2201 et du MDMB-CHMCZCA, Drug Testing and Analysis, 2018","pmid":"29726116","doi":"10.1002/dta.2398","url":"https://pubmed.ncbi.nlm.nih.gov/29726116/"},{"label":"Wouters et coll., biais de signalisation entre 21 agonistes de synthèse des récepteurs CB1, ACS Pharmacology and Translational Science, 2020","pmid":"32296768","doi":"10.1021/acsptsci.9b00069","url":"https://pubmed.ncbi.nlm.nih.gov/32296768/"},{"label":"Bäckberg et coll., activité in vitro des agonistes de synthèse sur CB1 (stratégie suédoise), Forensic Science International, 2023","pmid":"37116244","doi":"10.1016/j.forsciint.2023.111691","url":"https://pubmed.ncbi.nlm.nih.gov/37116244/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, cannabinoïdes de synthèse","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Légifrance, arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 (liste des stupéfiants, cannabinoïdes de synthèse)","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"INCB, Liste verte 2026 (conventions de 1961 et 1971), consultée","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 118796466 (EG-018)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/118796466"}]},"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":"controlled-named","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 control measure taken at Union level has been found in the sources consulted for EG-018, so control currently falls under the national law of each Member State. The molecule is not listed in the international conventions of 1961 and 1971 (INCB Green List 2026 consulted). Regimes outside the Union were not checked for this record.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"A narcotic classified in France and cited by name in annex IV of the ANSM consolidated list of substances classified as narcotics (updated 16 February 2026), which compiles the decree of 22 February 1990 establishing the list of substances classified as narcotics and the ANSM decisions. It appears in the block of synthetic cannabinoids attached to the decree of 31 March 2017 that amends that decree. The text names EG-018 under its chemical designation, naphthalen-1-yl (9-pentyl-9H-carbazol-3-yl) methanone, together with their isomers, stereoisomers, esters, ethers and salts. The classification falls under Article L. 5132-7 of the French Public Health Code.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Gamage et coll., évaluation in vitro et in vivo de l'EG-018, Pharmacology Biochemistry and Behavior, 2020","pmid":"32247816","doi":"10.1016/j.pbb.2020.172918","url":"https://pubmed.ncbi.nlm.nih.gov/32247816/"},{"label":"Finlay et coll., déterminants de l'efficacité agoniste au récepteur CB1, analogues de l'EG-018, Pharmacology Research and Perspectives, 2022","pmid":"35041297","doi":"10.1002/prp2.901","url":"https://pubmed.ncbi.nlm.nih.gov/35041297/"},{"label":"Mogler et coll., métabolisme de phase I de l'EG-018, de l'EG-2201 et du MDMB-CHMCZCA, Drug Testing and Analysis, 2018","pmid":"29726116","doi":"10.1002/dta.2398","url":"https://pubmed.ncbi.nlm.nih.gov/29726116/"},{"label":"Wouters et coll., biais de signalisation entre 21 agonistes de synthèse des récepteurs CB1, ACS Pharmacology and Translational Science, 2020","pmid":"32296768","doi":"10.1021/acsptsci.9b00069","url":"https://pubmed.ncbi.nlm.nih.gov/32296768/"},{"label":"Bäckberg et coll., activité in vitro des agonistes de synthèse sur CB1 (stratégie suédoise), Forensic Science International, 2023","pmid":"37116244","doi":"10.1016/j.forsciint.2023.111691","url":"https://pubmed.ncbi.nlm.nih.gov/37116244/"},{"label":"ANSM, liste consolidée des substances classées comme stupéfiants (mise à jour du 16 février 2026), annexe IV, cannabinoïdes de synthèse","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"Légifrance, arrêté du 31 mars 2017 modifiant l'arrêté du 22 février 1990 (liste des stupéfiants, cannabinoïdes de synthèse)","pmid":null,"doi":null,"url":"https://www.legifrance.gouv.fr/jorf/id/JORFARTI000034372042"},{"label":"INCB, Liste verte 2026 (conventions de 1961 et 1971), consultée","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 118796466 (EG-018)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/118796466"}],"meta":{"slug":"eg-018","url":"https://en.phytogrammes.com/wiki/eg-018","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."}}