{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"CJAVPRNATZCNLN-NBRGKURFSA-N","prefName":"Serinolamide A","symbol":"Serinolamide A","iupacName":"(E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]-N-methyloctadec-4-enamide","aliases":["Serinolamide A","(4E)-N-[(2R)-1-Hydroxy-3-methoxy-2-propanyl]-N-methyl-4-octadecenamide"],"cas":null,"pubchemCid":"56597771","chebiId":"CHEBI:69065","smiles":"CCCCCCCCCCCCC/C=C/CCC(=O)N(C)[C@H](CO)COC","molecularFormula":"C23H45NO3","molecularWeight":383.6,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/56597771","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:CHEBI:69065"}},"classification":{"family":"ecs_tool","familyLabel":"ECS modulator (research)","origin":"synthetic","originLabel":"Synthétique","structuralClassFr":null},"originSynthesis":{"heading":"Origin (research tool)","summaryFr":"No biosynthetic pathway has been demonstrated experimentally. The authors of the isolation put forward a hypothesis: the fatty chain would derive from a polyketide synthase (PKS) pathway, the serinol unit from serine, and the methyl groups would be introduced by S-adenosylmethionine (SAM)-dependent methyltransferases. A total synthesis published in 2019 prepares the molecule in the laboratory by a convergent approach (Ghotekar et al., 2019).","originNote":"Marine cyanobacterium Lyngbya majuscula, collected off New Ireland (Papua New Guinea) in 2005. Serinolamides have also been described from a cyanobacterium of the genus Okeania collected in the Red Sea (Petitbois et al., 2017).","discovered":""},"pharmacology":{"summaryFr":"Serinolamide A is a fatty acid amide isolated in 2011 from the marine cyanobacterium Lyngbya majuscula, collected in Papua New Guinea, by Gutiérrez et al. Its structure, which recalls that of anandamide, led its authors to present it as a cannabinomimetic lipid. It displaces a radioligand from the human CB1 receptor with a Ki of 1.3 µM, a moderate affinity that the authors consider selective for this receptor, and it does not displace half of the radioligand from CB2 at 10 µM. No human or pharmacokinetic data has been published, and a total synthesis was described in 2019.","receptorSummaryFr":"On human CB1 and CB2 receptors, the isolation paper reports only radioligand displacement assays. On CB1, it displaces a reference radioligand with a Ki of 1.3 µM: a moderate affinity that its authors consider selective for this receptor and describe as a moderate agonist effect, with no functional assay described in the paper. On CB2, the concentration needed to displace half of the radioligand exceeds 10 µM. A 2022 study tested the molecule on the S1P1 receptor (sphingosine-1-phosphate), a target with no direct link to the endocannabinoid system (Park et al., 2022).","binding":[{"target":"CB1","efficacy":"full_agonist","relativeActivity":40,"reported":"Ki 1,3 µM (Gutiérrez et coll., 2011), effet agoniste modéré rapporté par les auteurs","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":5,"reported":"IC50 supérieure à 10 µM (Gutiérrez et coll., 2011) ; aucune constante d'affinité publiée","confidence":"medium"}],"references":[{"label":"Gutiérrez et coll., lipide cannabinomimétique d'une cyanobactérie marine (Lyngbya majuscula), Journal of Natural Products 2011","pmid":"21999614","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/21999614/"},{"label":"Montaser et coll., amides d'acides gras de cyanobactéries marines agissant sur les récepteurs cannabinoïdes, ChemBioChem 2012","pmid":"23143757","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23143757/"},{"label":"Ghotekar et coll., synthèse totale des produits naturels marins serinolamide A et columbamide D, ACS Omega 2019","pmid":"31459401","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31459401/"},{"label":"Park et coll., synthèse et évaluation de dérivés de la sérinolamide comme agonistes du récepteur S1P1, Molecules 2022","pmid":"35566164","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35566164/"},{"label":"Petitbois et coll., sérinolamides et lyngbyabellines d'une cyanobactérie Okeania sp. de la mer Rouge, Journal of Natural Products 2017","pmid":"29019684","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29019684/"},{"label":"PubChem CID 56597771 : sérinolamide A (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/56597771"},{"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, Liste verte 2026 (convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}]},"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":15},{"key":"focus","label":"Clarity","description":"Sustained attention and clear thinking; functional lucidity, not euphoria.","intensity":8},{"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":5},{"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":"No harmonised European Union control measure for serinolamide A has been identified in the sources consulted: the EU level sets no harmonised measure for this molecule, and control falls under national law.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Serinolamide A is not named on the French narcotics list (ANSM consolidated list, updated 16 February 2026). Its structure does not meet the generic family definitions of this list: it has no indole, indazole, pyrrole, naphthyl, cyclohexylphenol or thiazole core, nor the benzo[c]chromene nucleus, covered by a clause of the ANSM decision of 22 May 2024. It is also not on the INCB Green List 2026 (1971 Convention).","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Gutiérrez et coll., lipide cannabinomimétique d'une cyanobactérie marine (Lyngbya majuscula), Journal of Natural Products 2011","pmid":"21999614","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/21999614/"},{"label":"Montaser et coll., amides d'acides gras de cyanobactéries marines agissant sur les récepteurs cannabinoïdes, ChemBioChem 2012","pmid":"23143757","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/23143757/"},{"label":"Ghotekar et coll., synthèse totale des produits naturels marins serinolamide A et columbamide D, ACS Omega 2019","pmid":"31459401","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31459401/"},{"label":"Park et coll., synthèse et évaluation de dérivés de la sérinolamide comme agonistes du récepteur S1P1, Molecules 2022","pmid":"35566164","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/35566164/"},{"label":"Petitbois et coll., sérinolamides et lyngbyabellines d'une cyanobactérie Okeania sp. de la mer Rouge, Journal of Natural Products 2017","pmid":"29019684","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/29019684/"},{"label":"PubChem CID 56597771 : sérinolamide A (identifiants)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/56597771"},{"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, Liste verte 2026 (convention de 1971)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"}],"meta":{"slug":"serinolamide-a","url":"https://en.phytogrammes.com/wiki/serinolamide-a","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."}}