{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"NSOGAHPJIFTUHV-YINRMENDSA-N","prefName":"Levonantradol","symbol":"CP 50,556-1","iupacName":"[(6S,6aR,9R,10aR)-9-hydroxy-6-methyl-3-[(2R)-5-phenylpentan-2-yl]oxy-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl] acetate;hydrochloride","aliases":["Levonantradol","Levonantradol HCl","Levonantradol hydrochloride","CP-50556-1","CP 50556-1 hydrochloride","DA-52090"],"cas":null,"pubchemCid":"5361880","chebiId":null,"smiles":"C[C@H]1[C@@H]2CC[C@H](C[C@H]2C3=C(N1)C=C(C=C3OC(=O)C)O[C@H](C)CCCC4=CC=CC=C4)O.Cl","molecularFormula":"C27H36ClNO4","molecularWeight":474,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/5361880"}},"classification":{"family":"scra","familyLabel":"Synthetic cannabinoid (SCRA)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (pharmaceutical research → illicit market)","summaryFr":"No biosynthetic pathway: a synthetic chemical compound of the octahydrophenanthridine family, with no published natural equivalent in the sources consulted.","originNote":"Levonantradol (CP 50,556-1) is a synthetic cannabinoid of the nantradol family, a structurally novel compound related to cannabinoids (Milne et al., 1979). It forms an enantiomeric pair with dextronantradol, which is inactive in mice (Little et al., 1988). An encyclopedic source attributes its development to Pfizer (tertiary reference, Wikipedia); no primary source consulted confirms this.","discovered":""},"pharmacology":{"summaryFr":"Levonantradol (CP 50,556-1) is a synthetic cannabinoid of the nantradol family, whose levorotatory enantiomer is the active form. In mice, given intravenously, it is active between 0.123 and 1.5 mg/kg, whereas the dextrorotatory enantiomer is inactive (Little et al., 1988). It has an affinity (Ki) of 2.9 nM for rat CB1, a value listed in ChEMBL. Tested in chemotherapy and postoperative pain patients during the 1980s, it notably caused drowsiness, dizziness, hypotension and pain at the injection site as side effects; no data on non-medical use are published in the sources consulted.","receptorSummaryFr":"Levonantradol binds to the CB1 receptor. In mice given intravenously, it is active between 0.123 and 1.5 mg/kg, its dextrorotatory enantiomer being inactive; its effects (reduced spontaneous activity, antinociception, hypothermia, catalepsy) are described as cannabinoid-induced, and their stereoselectivity suggests a specific, receptor-type mechanism (Little et al., 1988). In neuroblastoma cell membranes, it inhibits adenylate cyclase at micromolar concentrations, stereoselectively (Howlett and Fleming, 1984). Its Ki at rat CB1 is 2.9 nM, a value listed in ChEMBL and drawn from Han et al., 2013. No CB2 affinity value was found in the sources consulted.","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":90,"reported":"Ki 2,9 nM sur le CB1 de rat, déplacement de [3H]SR141716A (valeur répertoriée par ChEMBL, issue de Han et coll., 2013)","confidence":"medium"}],"references":[{"label":"Little et coll., stéréosélectivité de cannabinoïdes structurellement nouveaux chez la souris, J Pharmacol Exp Ther 1988","pmid":"2849657","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2849657/"},{"label":"Howlett et Fleming, inhibition de l'adénylate cyclase dans des membranes de neuroblastome, Mol Pharmacol 1984","pmid":"6092901","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/6092901/"},{"label":"Han et coll., utilité thérapeutique des agonistes sélectifs du CB2, J Med Chem 2013","pmid":"23865723","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23865723/"},{"label":"Shepard, pharmacocinétique du levonantradol chez l'animal et l'humain, J Clin Pharmacol 1981","pmid":"7298868","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7298868/"},{"label":"Tyson et coll., essai de phase I du levonantradol dans les nausées induites par la chimiothérapie, Am J Clin Oncol 1985","pmid":"4083271","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4083271/"},{"label":"Citron et coll., efficacité antiémétique du levonantradol comparée au delta-9-THC, Cancer Treat Rep 1985","pmid":"2981616","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2981616/"},{"label":"Joss et coll., levonantradol, antiémétique à taux élevé d'effets indésirables, Cancer Chemother Pharmacol 1982","pmid":"7139853","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7139853/"},{"label":"Stambaugh et coll., évaluation de doses croissantes de levonantradol intramusculaire, J Clin Pharmacol 1984","pmid":"6392353","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/6392353/"},{"label":"Jain et coll., levonantradol intramusculaire et placebo dans la douleur postopératoire aiguë, J Clin Pharmacol 1981","pmid":"7028791","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7028791/"},{"label":"Sheshenev et coll., synthèse asymétrique et analyse structurale du levonantradol, Chem Commun 2013","pmid":"23535893","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23535893/"},{"label":"Milne et coll., activité analgésique stéréospécifique du nantradol, NIDA Res Monogr 1979","pmid":"121368","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/121368/"},{"label":"ANSM, liste consolidée des stupéfiants, mise à jour du 16 février 2026","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (conventions de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 5361880 (chlorhydrate de levonantradol)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/5361880"},{"label":"ChEMBL, CHEMBL2111116 (données d'activité CB1)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL2111116/"},{"label":"Wikipédia, Levonantradol (repère tertiaire)","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/Levonantradol"}]},"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":55},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":10},{"key":"sleep","label":"Sleep","description":"Sedative effect: aids sleep onset and the continuity of deep sleep.","intensity":25},{"key":"appetite","label":"Appetite","description":"Stimulation of hunger and of taste appreciation (the “munchies” effect).","intensity":10},{"key":"uplift","label":"High","description":"Euphoria and sensory intensity; altered perception of time and space.","intensity":5}],"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":"At European Union level, no harmonised control measure has been identified for this molecule in the sources consulted; control falls under national law.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Levonantradol is not named in the ANSM consolidated list of narcotics (update of 16 February 2026) and does not appear in the INCB Green List 2026 (1971 Convention schedules). Its structure does not meet the definition of cyclohexylphenols or 2-(3-hydroxycyclohexyl)phenol derivatives, because the substituent at position 5 of the phenol ring is an ether (O-alkyl) rather than an alkyl group bonded directly to the ring. It also does not meet the tetrahydrocannabinol definition (ministerial order of 22 February 1990) or the benzo[c]chromene definition (decision of 22 May 2024), its core being nitrogenous.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Little et coll., stéréosélectivité de cannabinoïdes structurellement nouveaux chez la souris, J Pharmacol Exp Ther 1988","pmid":"2849657","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2849657/"},{"label":"Howlett et Fleming, inhibition de l'adénylate cyclase dans des membranes de neuroblastome, Mol Pharmacol 1984","pmid":"6092901","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/6092901/"},{"label":"Han et coll., utilité thérapeutique des agonistes sélectifs du CB2, J Med Chem 2013","pmid":"23865723","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23865723/"},{"label":"Shepard, pharmacocinétique du levonantradol chez l'animal et l'humain, J Clin Pharmacol 1981","pmid":"7298868","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7298868/"},{"label":"Tyson et coll., essai de phase I du levonantradol dans les nausées induites par la chimiothérapie, Am J Clin Oncol 1985","pmid":"4083271","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/4083271/"},{"label":"Citron et coll., efficacité antiémétique du levonantradol comparée au delta-9-THC, Cancer Treat Rep 1985","pmid":"2981616","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/2981616/"},{"label":"Joss et coll., levonantradol, antiémétique à taux élevé d'effets indésirables, Cancer Chemother Pharmacol 1982","pmid":"7139853","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7139853/"},{"label":"Stambaugh et coll., évaluation de doses croissantes de levonantradol intramusculaire, J Clin Pharmacol 1984","pmid":"6392353","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/6392353/"},{"label":"Jain et coll., levonantradol intramusculaire et placebo dans la douleur postopératoire aiguë, J Clin Pharmacol 1981","pmid":"7028791","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/7028791/"},{"label":"Sheshenev et coll., synthèse asymétrique et analyse structurale du levonantradol, Chem Commun 2013","pmid":"23535893","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23535893/"},{"label":"Milne et coll., activité analgésique stéréospécifique du nantradol, NIDA Res Monogr 1979","pmid":"121368","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/121368/"},{"label":"ANSM, liste consolidée des stupéfiants, mise à jour du 16 février 2026","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"INCB, Green List 2026 (conventions de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem, CID 5361880 (chlorhydrate de levonantradol)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/5361880"},{"label":"ChEMBL, CHEMBL2111116 (données d'activité CB1)","pmid":null,"doi":null,"url":"https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL2111116/"},{"label":"Wikipédia, Levonantradol (repère tertiaire)","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/Levonantradol"}],"meta":{"slug":"cp-50-556-1","url":"https://en.phytogrammes.com/wiki/cp-50-556-1","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."}}