{"schemaVersion":"cwiki-fiche-2.0","identifiers":{"inchiKey":"UAHWPYUMFXYFJY-UHFFFAOYSA-N","prefName":"Myrcene","symbol":"Myrcene","iupacName":"7-méthyl-3-méthylidèneocta-1,6-diène","aliases":["β-myrcène","bêta-myrcène","myrcene","β-myrcene","β-géraniolène","7-méthyl-3-méthylène-1,6-octadiène","FEMA 2762"],"cas":"123-35-3","pubchemCid":"31253","chebiId":"CHEBI:17221","smiles":"CC(=CCCC(=C)C=C)C","molecularFormula":"C10H16","molecularWeight":136.23,"xrefs":{"pubchem":"https://pubchem.ncbi.nlm.nih.gov/compound/31253","chebi":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:CHEBI:17221"}},"classification":{"family":"terpene","familyLabel":"Terpene","origin":"plant","originLabel":"Plante","subgroup":"monoterpene","subgroupLabel":"Monoterpene","originCode":"E","originCodeLabel":"Enzymatic biosynthesis in the plant","originDebated":false,"chemicalClass":"Monoterpène acyclique (sans activité mesurée sur CB1 ni CB2)","sideChain":null,"form":null,"parent":null,"pharmacologicalClass":null,"naturalTrace":null,"structuralClassFr":null},"originSynthesis":{"heading":"Biosynthetic pathway","summaryFr":"An acyclic monoterpene formed from geranyl pyrophosphate (GPP) by terpene synthases. GPP, the ten-carbon precursor of monoterpenes, usually derived from the MEP pathway, is also a building block of cannabinoid biosynthesis (Booth 2017). In hemp, two single-product myrcene synthases have been functionally characterised: CsTPS3FN, from the 'Finola' variety, and CsTPS30PK, from the Purple Kush variety, which form only myrcene from GPP and share only 54.5% amino-acid identity; other hemp terpene synthases also produce it, including CsTPS5FN, for which it is the main monoterpene (37% of products) (Booth 2017).","originNote":"A monoterpene very widespread in the plant kingdom: a major constituent of hop essential oil (NTP 2010), identified as the main analgesic component of lemongrass essential oil, Cymbopogon citratus (Lorenzetti 1991), and also present in citrus fruit (FDA 2018). Hemp makes it itself: in the female inflorescences of 22 plants of the 'Finola' variety it accounted on average for 27 ± 21% of the monoterpenes (Booth 2017), and, together with β-caryophyllene and limonene, it is one of the three terpenes with the highest average levels in 42 843 samples of commercial cannabis analysed in the United States (Smith 2022). It is a terpene, not a cannabinoid.","discovered":""},"pharmacology":{"summaryFr":"Myrcene (β-myrcene) is an acyclic monoterpene, one of the most abundant terpenes in cannabis; it is a terpene, not a cannabinoid. Three in vitro studies measured no direct activity at human CB1 and CB2 receptors, neither binding, nor activation, nor modulation of the response to Δ9-THC (Santiago 2019; Finlay 2020; Alayoubi 2025): these results do not support the hypothesis of an 'entourage effect' acting through these receptors. In animals it has shown antinociceptive effects in mice (Rao 1990; Alayoubi 2025) and in rats (Lorenzetti 1991; McDougall 2022), sometimes blocked by cannabinoid antagonists, as well as sedative and muscle-relaxant effects in mice at 100 and 200 mg/kg intraperitoneally, with a roughly 2.6-fold prolongation of barbiturate-induced sleep at 200 mg/kg (do Vale 2002). In vitro it also activates the TRPV1 channel (Jansen 2019). No study of its pharmacokinetics in humans had been published according to the National Toxicology Program (NTP 2010), and a 2021 review notes that human studies are lacking (Surendran 2021). Given by gavage at high doses for two years, it induced kidney tumours in male rats and liver tumours in male mice (NTP 2010); the International Agency for Research on Cancer classified it in Group 2B, and in 2018 the FDA removed synthetic myrcene from the list of authorised flavourings under the Delaney Clause, while judging it unlikely to induce tumours in humans at current exposure levels.","receptorSummaryFr":"No measurable activity at human cannabinoid receptors in three in vitro studies. In AtT20 cells expressing human CB1 or CB2 it caused no hyperpolarisation up to 30 µM and changed neither the response to Δ9-THC nor that to CP55,940 (Santiago 2019). At 10 µM it did not displace [3H]CP55,940 from membranes of HEK cells expressing human CB1 or CB2, nor did it change cAMP signalling, alone or combined with Δ9-THC or 2-AG (Finlay 2020). Again at 10 µM, it did not activate the Gi protein coupled to human CB1 in HEK293T cells and changed neither the response to CP55,940 nor those to 2-AG and anandamide (Alayoubi 2025). The study by LaVigne et al. (2021), which describes other cannabis terpenes as cannabimimetic at CB1, did not test myrcene. In vivo, however, antinociceptive effects sensitive to cannabinoid antagonists have been reported: in mice with chronic constriction of the sciatic nerve, the effect of 100 and 200 mg/kg given intraperitoneally was reversed by SR141716, a CB1 antagonist (Alayoubi 2025); in rats with Freund's adjuvant monoarthritis, the analgesic effect of locally injected myrcene (1 and 5 mg/kg subcutaneously) was blocked by AM281 (CB1) as well as by AM630 (CB2) (McDougall 2022). The 2025 authors propose an indirect engagement of the endocannabinoid system, which they did not demonstrate. Outside the cannabinoid receptors, it activates the TRPV1 channel at micromolar concentrations in HEK cells (Jansen 2019) and competitively inhibits CYP2B1 in rat liver microsomes (Ki = 0.14 µM; De-Oliveira 1997).","binding":[{"target":"CB1","efficacy":"unknown","measure":null,"valueNm":null,"species":"human","assay":"membrane potential (FLIPR), AtT20 cells expressing human CB1; alone from 300 pM to 30 µM, and at 100 nM or 10 µM combined with Δ9-THC (10 µM)","source":{"label":"Santiago et al. 2019, Cannabis Cannabinoid Res","pmid":"31559333","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31559333/"},"strength":null,"reported":"No hyperpolarisation; responses to Δ9-THC and CP55,940 unchanged","confidence":"low"},{"target":"CB2","efficacy":"unknown","measure":null,"valueNm":null,"species":"human","assay":"membrane potential (FLIPR), AtT20 cells expressing human CB2; alone from 300 pM to 30 µM, and at 100 nM or 10 µM combined with Δ9-THC (10 µM)","source":{"label":"Santiago et al. 2019, Cannabis Cannabinoid Res","pmid":"31559333","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31559333/"},"strength":null,"reported":"No hyperpolarisation; responses to Δ9-THC and CP55,940 unchanged","confidence":"low"},{"target":"CB1","efficacy":"unknown","measure":null,"valueNm":null,"species":"human","assay":"[3H]CP55,940 displacement on HEK cell membranes and cAMP (CAMYEL BRET), human CB1; 10 µM","source":{"label":"Finlay et al. 2020, Front Pharmacol","pmid":"32269529","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/32269529/"},"strength":null,"reported":"No radioligand displacement and no effect on cAMP, alone or with Δ9-THC or 2-AG","confidence":"low"},{"target":"CB2","efficacy":"unknown","measure":null,"valueNm":null,"species":"human","assay":"[3H]CP55,940 displacement on HEK cell membranes and cAMP (CAMYEL BRET), human CB2; 10 µM","source":{"label":"Finlay et al. 2020, Front Pharmacol","pmid":"32269529","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/32269529/"},"strength":null,"reported":"No radioligand displacement and no effect on cAMP, alone or with Δ9-THC or 2-AG","confidence":"low"},{"target":"CB1","efficacy":"unknown","measure":null,"valueNm":null,"species":"human","assay":"Gαi1 and Gαo protein activation (TRUPATH BRET), HEK293T cells expressing human CB1; 10 µM","source":{"label":"Alayoubi et al. 2025, Pain","pmid":"40839768","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/40839768/"},"strength":null,"reported":"No Gi activation; responses to CP55,940, 2-AG and anandamide unchanged","confidence":"low"},{"target":"TRPV1","efficacy":"full_agonist","measure":null,"valueNm":null,"species":"human and rat","assay":"calcium flux and patch-clamp currents, HEK cells with inducible expression of human or rat TRPV1; response inhibited by capsazepine","source":{"label":"Jansen et al. 2019, Channels (Austin)","pmid":"31446830","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/31446830/"},"strength":null,"reported":"Activation at micromolar concentrations (high-amplitude currents at 150 µM); no EC50 reported","confidence":"low"},{"target":"CYP2B1","efficacy":"inhibitor","measure":"Ki","valueNm":140,"species":"rat","assay":"pentoxyresorufin-O-depentylase (PROD) activity, liver microsomes from phenobarbital-treated rats; competitive inhibition (IC50 = 0.14 µM)","source":{"label":"De-Oliveira et al. 1997, Toxicol Lett","pmid":"9242356","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9242356/"},"strength":48,"reported":null,"confidence":"high"}],"references":[{"label":"Santiago M et al. Absence of Entourage: Terpenoids Commonly Found in Cannabis sativa Do Not Modulate the Functional Activity of Δ9-THC at Human CB1 and CB2 Receptors. Cannabis Cannabinoid Res, 2019","pmid":"31559333","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC6757242/"},{"label":"Finlay DB et al. Terpenoids From Cannabis Do Not Mediate an Entourage Effect by Acting at Cannabinoid Receptors. Front Pharmacol, 2020","pmid":"32269529","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC7109307/"},{"label":"Alayoubi M et al. Elucidating interplay between myrcene and cannabinoid receptor 1 receptors to produce antinociception in mouse models of neuropathic pain. Pain, 2025","pmid":"40839768","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC12353019/"},{"label":"LaVigne JE et al. Cannabis sativa terpenes are cannabimimetic and selectively enhance cannabinoid activity. Sci Rep, 2021","pmid":"33859287","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC8050080/"},{"label":"McDougall JJ, McKenna MK. Anti-Inflammatory and Analgesic Properties of the Cannabis Terpene Myrcene in Rat Adjuvant Monoarthritis. Int J Mol Sci, 2022","pmid":"35887239","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9319952/"},{"label":"Booth JK et al. Terpene synthases from Cannabis sativa. PLoS One, 2017","pmid":"28355238","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC5371325/"},{"label":"Smith CJ et al. The phytochemical diversity of commercial Cannabis in the United States. PLoS One, 2022","pmid":"35588111","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9119530/"},{"label":"National Toxicology Program. Toxicology and carcinogenesis studies of beta-myrcene (CAS No. 123-35-3) in F344/N rats and B6C3F1 mice (gavage studies). NTP TR 557, 2010","pmid":"21415873","doi":null,"url":"https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/lt_rpts/tr557.pdf"},{"label":"IARC Monographs Volume 119: Some Chemicals That Cause Tumours of the Urinary Tract in Rodents, 2019 (beta-myrcene, Group 2B)","pmid":null,"doi":null,"url":"https://publications.iarc.who.int/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Some-Chemicals-That-Cause-Tumours-Of-The-Urinary-Tract-In-Rodents-2019"},{"label":"FDA. Food Additive Regulations; Synthetic Flavoring Agents and Adjuvants. Federal Register 83 FR 50490, 9 October 2018","pmid":null,"doi":null,"url":"https://www.govinfo.gov/content/pkg/FR-2018-10-09/pdf/2018-21807.pdf"},{"label":"Commission Implementing Regulation (EU) No 872/2012, Union list of flavouring substances (FL No 01.008, myrcene)","pmid":null,"doi":null,"url":"https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32012R0872"},{"label":"Madyastha KM, Srivatsan V. Metabolism of beta-myrcene in vivo and in vitro: its effects on rat-liver microsomal enzymes. Xenobiotica, 1987","pmid":"3604259","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/3604259/"},{"label":"De-Oliveira AC et al. In vitro inhibition of CYP2B1 monooxygenase by beta-myrcene and other monoterpenoid compounds. Toxicol Lett, 1997","pmid":"9242356","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9242356/"},{"label":"Freitas JC et al. Effect of beta-myrcene on pentobarbital sleeping time. Braz J Med Biol Res, 1993","pmid":"8257941","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/8257941/"},{"label":"Jansen C et al. Myrcene and terpene regulation of TRPV1. Channels (Austin), 2019","pmid":"31446830","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC6768052/"},{"label":"Rao VS et al. Effect of myrcene on nociception in mice. J Pharm Pharmacol, 1990","pmid":"1983154","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1983154/"},{"label":"Lorenzetti BB et al. Myrcene mimics the peripheral analgesic activity of lemongrass tea. J Ethnopharmacol, 1991","pmid":"1753786","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1753786/"},{"label":"do Vale TG et al. Central effects of citral, myrcene and limonene, constituents of essential oil chemotypes from Lippia alba. Phytomedicine, 2002","pmid":"12587690","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/12587690/"},{"label":"Delgado IF et al. Study on embryo-foetotoxicity of beta-myrcene in the rat. Food Chem Toxicol, 1993","pmid":"8444385","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/8444385/"},{"label":"Surendran S et al. Myrcene, what are the potential health benefits of this flavouring and aroma agent? Front Nutr, 2021","pmid":"34350208","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC8326332/"}]},"pharmacokinetics":null,"metabolism":null,"detection":null,"subjectiveEffects":{"state":"uncharacterised","method":"https://en.phytogrammes.com/wiki/a-propos#methode-effets","axes":[],"doseRanges":null,"humanDataCharacterised":true},"indications":{"approvedMedicines":[]},"harmProfile":{"unstudiedBanner":false,"bannerTextFr":null,"toxicologyFr":null},"legal":{"scheduleStatus":"unscheduled","scheduleLabel":"Unscheduled","frScheduleStatus":"unscheduled","tiers":[{"jurisdiction":"international","jurisdictionLabel":"International","label":null,"reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-10-20","supersededBy":null},{"jurisdiction":"eu","jurisdictionLabel":"Union européenne","label":"Myrcene is on the Union list of flavouring substances (Annex I to Regulation (EC) No 1334/2008, established by Implementing Regulation (EU) No 872/2012) under number FL 01.008, for all categories of flavoured foods; footnote 4 required additional scientific data by 31 December 2013, and the Commission's portal states that these data have been submitted and that the EFSA evaluation remains to be completed. ECHA lists no harmonised classification under the CLP Regulation for it. It appears in no schedule of the 1961 and 1971 United Nations conventions (INCB Yellow List, 65th edition, 2026; Green List, 36th edition, 2025).","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-10-20","supersededBy":null},{"jurisdiction":"fr","jurisdictionLabel":"France","label":"Not classified as a narcotic or as a psychotropic substance in France: myrcene appears neither in the ANSM consolidated list of narcotics (updated 26/06/2026), which compiles the order of 22 February 1990 and the Agency's decisions, nor in the consolidated list of psychotropic substances (17/02/2026). An acyclic monoterpene without a cannabinoid skeleton, it does not fall within the generic class of the benzo[c]chromene nucleus (ANSM decisions of 2024). Used as a flavouring, it is governed by EU food law.","reference":null,"url":null,"effectiveDate":null,"lastVerified":"2026-10-20","supersededBy":null}],"sourcesFr":"EUR-Lex, UNODC, CND, ANSM, IUPHAR/BPS, ChEBI, EUDA."},"references":[{"label":"Santiago M et al. Absence of Entourage: Terpenoids Commonly Found in Cannabis sativa Do Not Modulate the Functional Activity of Δ9-THC at Human CB1 and CB2 Receptors. Cannabis Cannabinoid Res, 2019","pmid":"31559333","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC6757242/"},{"label":"Finlay DB et al. Terpenoids From Cannabis Do Not Mediate an Entourage Effect by Acting at Cannabinoid Receptors. Front Pharmacol, 2020","pmid":"32269529","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC7109307/"},{"label":"Alayoubi M et al. Elucidating interplay between myrcene and cannabinoid receptor 1 receptors to produce antinociception in mouse models of neuropathic pain. Pain, 2025","pmid":"40839768","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC12353019/"},{"label":"LaVigne JE et al. Cannabis sativa terpenes are cannabimimetic and selectively enhance cannabinoid activity. Sci Rep, 2021","pmid":"33859287","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC8050080/"},{"label":"McDougall JJ, McKenna MK. Anti-Inflammatory and Analgesic Properties of the Cannabis Terpene Myrcene in Rat Adjuvant Monoarthritis. Int J Mol Sci, 2022","pmid":"35887239","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9319952/"},{"label":"Booth JK et al. Terpene synthases from Cannabis sativa. PLoS One, 2017","pmid":"28355238","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC5371325/"},{"label":"Smith CJ et al. The phytochemical diversity of commercial Cannabis in the United States. PLoS One, 2022","pmid":"35588111","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9119530/"},{"label":"National Toxicology Program. Toxicology and carcinogenesis studies of beta-myrcene (CAS No. 123-35-3) in F344/N rats and B6C3F1 mice (gavage studies). NTP TR 557, 2010","pmid":"21415873","doi":null,"url":"https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/lt_rpts/tr557.pdf"},{"label":"IARC Monographs Volume 119: Some Chemicals That Cause Tumours of the Urinary Tract in Rodents, 2019 (beta-myrcene, Group 2B)","pmid":null,"doi":null,"url":"https://publications.iarc.who.int/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Some-Chemicals-That-Cause-Tumours-Of-The-Urinary-Tract-In-Rodents-2019"},{"label":"FDA. Food Additive Regulations; Synthetic Flavoring Agents and Adjuvants. Federal Register 83 FR 50490, 9 October 2018","pmid":null,"doi":null,"url":"https://www.govinfo.gov/content/pkg/FR-2018-10-09/pdf/2018-21807.pdf"},{"label":"Commission Implementing Regulation (EU) No 872/2012, Union list of flavouring substances (FL No 01.008, myrcene)","pmid":null,"doi":null,"url":"https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:32012R0872"},{"label":"Madyastha KM, Srivatsan V. Metabolism of beta-myrcene in vivo and in vitro: its effects on rat-liver microsomal enzymes. Xenobiotica, 1987","pmid":"3604259","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/3604259/"},{"label":"De-Oliveira AC et al. In vitro inhibition of CYP2B1 monooxygenase by beta-myrcene and other monoterpenoid compounds. Toxicol Lett, 1997","pmid":"9242356","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/9242356/"},{"label":"Freitas JC et al. Effect of beta-myrcene on pentobarbital sleeping time. Braz J Med Biol Res, 1993","pmid":"8257941","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/8257941/"},{"label":"Jansen C et al. Myrcene and terpene regulation of TRPV1. Channels (Austin), 2019","pmid":"31446830","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC6768052/"},{"label":"Rao VS et al. Effect of myrcene on nociception in mice. J Pharm Pharmacol, 1990","pmid":"1983154","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1983154/"},{"label":"Lorenzetti BB et al. Myrcene mimics the peripheral analgesic activity of lemongrass tea. J Ethnopharmacol, 1991","pmid":"1753786","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/1753786/"},{"label":"do Vale TG et al. Central effects of citral, myrcene and limonene, constituents of essential oil chemotypes from Lippia alba. Phytomedicine, 2002","pmid":"12587690","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/12587690/"},{"label":"Delgado IF et al. Study on embryo-foetotoxicity of beta-myrcene in the rat. Food Chem Toxicol, 1993","pmid":"8444385","doi":null,"url":"https://pubmed.ncbi.nlm.nih.gov/8444385/"},{"label":"Surendran S et al. Myrcene, what are the potential health benefits of this flavouring and aroma agent? Front Nutr, 2021","pmid":"34350208","doi":null,"url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC8326332/"}],"meta":{"slug":"myrcene","url":"https://en.phytogrammes.com/wiki/myrcene","lastVerified":"2026-10-20","dataUpdatedAt":"2026-10-27","confidence":"high","dataCompletenessPct":80,"audit":null,"wikipedia":null,"disclaimerFr":"Contenu éditorial informatif, sans valeur d'avis médical ni juridique. Sources primaires citées par fiche. Réservé aux adultes."}}