{"schemaVersion":"cwiki-fiche-1.0","identifiers":{"inchiKey":"OORFXDSWECAQLI-UHFFFAOYSA-N","prefName":"Parahexyl","symbol":"Synhexyl","iupacName":"3-hexyl-6,6,9-trimethyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-ol","aliases":["Synhexyl","Parahexyl","Pyrahexyl","3-Homotetrahydrocannabinol"],"cas":"117-51-1","pubchemCid":"8334","chebiId":null,"smiles":"CCCCCCC1=CC2=C(C3=C(CCC(C3)C)C(O2)(C)C)C(=C1)O","molecularFormula":"C22H32O2","molecularWeight":328.5,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/8334"}},"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 described: the compound is obtained by chemical synthesis, and a 1968 study (Hollister et al.) describes it as semisynthetic.","originNote":"Synthetic molecule, created in the laboratory to study homologues of tetrahydrocannabinol. No natural occurrence is recorded.","discovered":""},"pharmacology":{"summaryFr":"Synhexyl, also called parahexyl, is a homologue of tetrahydrocannabinol with a hexyl side chain, linked to the work of Roger Adams and his collaborators on THC homologues published in 1941. Several publications, between 1948 and 1970, describe it in humans, including a direct comparison with THC in 1968. No affinity constant for CB1 or CB2 is published, and no measurement of its activity at these receptors has been found. It is named as a narcotic in the French list of narcotics, annex III, and appears in Schedule I of the 1971 Convention on Psychotropic Substances.","receptorSummaryFr":"No published affinity constant for CB1 or CB2 was found, neither in PubMed nor in ChEMBL, and no functional measurement is reported. CB1 activity is presumed by analogy with THC, without confirmation by measurement.","binding":[{"target":"CB1","efficacy":"modulator","relativeActivity":8,"reported":"Aucune constante d'affinité publiée ; aucune mesure d'activité retrouvée","confidence":"medium"},{"target":"CB2","efficacy":"modulator","relativeActivity":8,"reported":"Aucune constante d'affinité publiée ; aucune mesure d'activité retrouvée","confidence":"medium"}],"references":[{"label":"Adams R., Loewe S., Jelinek C. et Wolff H., Homologues du tétrahydrocannabinol à activité marihuana, IX, Journal of the American Chemical Society, 1941","pmid":null,"doi":"10.1021/ja01852a052","url":"https://doi.org/10.1021/ja01852a052"},{"label":"Williams E. G. et Himmelsbach C. K., Études sur la marihuana et le composé pyrahexyl, Public Health Reports, 1946","pmid":"20992145","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/20992145/"},{"label":"Pond D. A., Effets psychologiques du synhexyl chez des patients dépressifs, Journal of Neurology, Neurosurgery and Psychiatry, 1948","pmid":"18894648","doi":"10.1136/jnnp.11.4.271","url":"https://pubmed.ncbi.nlm.nih.gov/18894648/"},{"label":"Thompson L. J. et Proctor R. C., Emploi du pyrahexyl dans les états de sevrage alcoolique et médicamenteux, North Carolina Medical Journal, 1953","pmid":"13099650","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/13099650/"},{"label":"Hollister L. E., Richards R. K. et Gillespie H. K., Comparaison du tétrahydrocannabinol et du synhexyl chez l'humain, Clinical Pharmacology and Therapeutics, 1968","pmid":"5721981","doi":"10.1002/cpt196896783","url":"https://pubmed.ncbi.nlm.nih.gov/5721981/"},{"label":"Hollister L. E., Moore F., Kanter S. et Noble E., Δ1-tétrahydrocannabinol, synhexyl et extrait de marihuana administrés par voie orale chez l'humain : catécholamines, cortisol et sérotonine plaquettaire, Psychopharmacologia, 1970","pmid":"5523370","doi":"10.1007/BF00404241","url":"https://pubmed.ncbi.nlm.nih.gov/5523370/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe III, parahexyl)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"OICS, Liste verte (Green List) des substances psychotropes sous contrôle international, tableau I, code PP 001 (parahexyl)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem CID 8334 : synhexyl (identifiants et masse moléculaire)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/8334"},{"label":"Parahexyl, article Wikipedia (repère tertiaire)","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/Parahexyl"}]},"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":"controlled-named","scheduleLabel":"Narcotic: named in schedule","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":"At European Union level there is no harmonised control measure targeting this compound: control is a matter for the Member States.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-05-01","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Named as a narcotic in France: parahexyl appears in annex III of the consolidated list of narcotics, updated on 16 February 2026, under the order of 22 February 1990, as amended by the order of 24 March 2000. Parahexyl is preceded by an asterisk in that list, which extends the classification to its stereoisomers where they can exist under the chemical designation given. The list is drawn up 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":"Adams R., Loewe S., Jelinek C. et Wolff H., Homologues du tétrahydrocannabinol à activité marihuana, IX, Journal of the American Chemical Society, 1941","pmid":null,"doi":"10.1021/ja01852a052","url":"https://doi.org/10.1021/ja01852a052"},{"label":"Williams E. G. et Himmelsbach C. K., Études sur la marihuana et le composé pyrahexyl, Public Health Reports, 1946","pmid":"20992145","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/20992145/"},{"label":"Pond D. A., Effets psychologiques du synhexyl chez des patients dépressifs, Journal of Neurology, Neurosurgery and Psychiatry, 1948","pmid":"18894648","doi":"10.1136/jnnp.11.4.271","url":"https://pubmed.ncbi.nlm.nih.gov/18894648/"},{"label":"Thompson L. J. et Proctor R. C., Emploi du pyrahexyl dans les états de sevrage alcoolique et médicamenteux, North Carolina Medical Journal, 1953","pmid":"13099650","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/13099650/"},{"label":"Hollister L. E., Richards R. K. et Gillespie H. K., Comparaison du tétrahydrocannabinol et du synhexyl chez l'humain, Clinical Pharmacology and Therapeutics, 1968","pmid":"5721981","doi":"10.1002/cpt196896783","url":"https://pubmed.ncbi.nlm.nih.gov/5721981/"},{"label":"Hollister L. E., Moore F., Kanter S. et Noble E., Δ1-tétrahydrocannabinol, synhexyl et extrait de marihuana administrés par voie orale chez l'humain : catécholamines, cortisol et sérotonine plaquettaire, Psychopharmacologia, 1970","pmid":"5523370","doi":"10.1007/BF00404241","url":"https://pubmed.ncbi.nlm.nih.gov/5523370/"},{"label":"ANSM, Liste consolidée des substances classées comme stupéfiants, mise à jour du 16 février 2026 (annexe III, parahexyl)","pmid":null,"doi":null,"url":"https://ansm.sante.fr/uploads/2026/02/17/20260217-stupefiants-liste-consolidee.pdf"},{"label":"OICS, Liste verte (Green List) des substances psychotropes sous contrôle international, tableau I, code PP 001 (parahexyl)","pmid":null,"doi":null,"url":"https://www.incb.org/incb/uploads/documents/Psychotropics/forms/greenlist/2026/2510307E.pdf"},{"label":"PubChem CID 8334 : synhexyl (identifiants et masse moléculaire)","pmid":null,"doi":null,"url":"https://pubchem.ncbi.nlm.nih.gov/compound/8334"},{"label":"Parahexyl, article Wikipedia (repère tertiaire)","pmid":null,"doi":null,"url":"https://en.wikipedia.org/wiki/Parahexyl"}],"meta":{"slug":"synhexyl","url":"https://en.phytogrammes.com/wiki/synhexyl","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."}}