caryophyllene

Caryophyllene can be produced synthetically,{{cite journal |last1=Corey |first1=E. J. |last2=Mitra |first2=R. B. |last3=Uda |first3=H. |title=Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene |journal=Journal of the American Chemical Society |year=1964 |volume=86 |issue=3 |pages=485–492 |doi=10.1021/ja01057a040|bibcode=1964JAChS..86..485C }} but it is invariably obtained from natural sources because it is widespread. It is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer.

Caryophyllene is one of the chemical compounds that contributes to the aroma of black pepper.{{cite journal |last1=Jirovetz |first1=L. |last2=Buchbauer |first2=G. |last3=Ngassoum |first3=M. B. |last4=Geissler |first4=M. |title=Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction–gas chromatography, solid-phase microextraction–gas chromatography–mass spectrometry and olfactometry |journal=Journal of Chromatography A |volume=976 |issue=1–2 |pages=265–275 |date=November 2002 |pmid=12462618 |doi= 10.1016/S0021-9673(02)00376-X}}

β-Caryophyllene is under basic research for its potential action as an agonist of the cannabinoid receptor type 2 (CB₂ receptor).{{cite journal |last1=Ceccarelli |first1=Ilaria |last2=Fiorenzani |first2=Paolo |last3=Pessina |first3=Federica |last4=Pinassi |first4=Jessica |last5=Aglianò |first5=Margherita |last6=Miragliotta |first6=Vincenzo |last7=Aloisi |first7=Anna Maria |title=The CB2 Agonist β-Caryophyllene in Male and Female Rats Exposed to a Model of Persistent Inflammatory Pain |journal=Frontiers in Neuroscience |date=18 August 2020 |volume=14 |pages=850 |doi=10.3389/fnins.2020.00850| pmc=7461959 |pmid=33013287 |doi-access=free }} In other basic studies, β-caryophyllene has a binding affinity of K_i = 155 nM at the CB₂ receptors.{{cite journal |last1=Alberti |first1=Thaís Barbosa |last2=Barbosa |first2=Wagner Luiz Ramos |last3=Vieira |first3=José Luiz Fernandes |last4=Raposo |first4=Nádia Rezende Barbosa |last5=Dutra |first5=Rafael Cypriano |title=(−)-β-Caryophyllene, a CB2 Receptor-Selective Phytocannabinoid, Suppresses Motor Paralysis and Neuroinflammation in a Murine Model of Multiple Sclerosis |journal=International Journal of Molecular Sciences |date=1 April 2017 |volume=18 |issue=4 |pages=691 |doi=10.3390/ijms18040691 |pmid=28368293 |pmc=5412277 |doi-access=free }}

β-Caryophyllene has the highest cannabinoid activity compared to the ring opened isomer α-caryophyllene humulene which may modulate CB₂ activity.{{cite journal |last1=Hashiesh |first1=Hebaallah Mamdouh |last2=Sharma |first2=Charu |last3=Goyal |first3=Sameer N. |last4=Sadek |first4=Bassem |last5=Jha |first5=Niraj Kumar |last6=Kaabi |first6=Juma Al |last7=Ojha |first7=Shreesh |title=A focused review on CB2 receptor-selective pharmacological properties and therapeutic potential of β-caryophyllene, a dietary cannabinoid |journal=Biomedicine & Pharmacotherapy |date=1 August 2021 |volume=140 |pages=111639 |doi=10.1016/j.biopha.2021.111639 |pmid=34091179 |s2cid=235362290 |doi-access=free }} To compare binding, cannabinol binds to the CB₂ receptors as a partial agonist with an affinity of K_i = 126.4 nM,{{cite book |last1=Russo |first1=Ethan B. |last2=Marcu |first2=Jahan |title=Cannabinoid Pharmacology |chapter=Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads |series=Advances in Pharmacology |date=2017 |volume=80 |pages=67–134 |doi=10.1016/bs.apha.2017.03.004 |pmid=28826544 |isbn=978-0-12-811232-8 }} while delta-9-tetrahydrocannabinol binds to the CB₂ receptors as a partial agonist with an affinity of K_i = 36 nM.{{cite journal |last1=Bow |first1=Eric W. |last2=Rimoldi |first2=John M. |title=The Structure–Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation |journal=Perspectives in Medicinal Chemistry |date=28 June 2016 |volume=8 |pages=17–39 |doi=10.4137/PMC.S32171 |pmid=27398024 |pmc=4927043 }}

== Safety ==

Caryophyllene has been given generally recognized as safe (GRAS) designation by the FDA and is approved by the FDA for use as a food additive, typically for flavoring.{{cite web |title=Nomination Background: beta-Caryophyllene (CASRN: 87-44-5) |url=https://ntp.niehs.nih.gov/sites/default/files/ntp/htdocs/chem_background/exsumpdf/betacaryophyllene_508.pdf }}{{Cite web|url=https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.515&SearchTerm=caryophyllene|title = CFR - Code of Federal Regulations Title 21}} Rats given up to 700 mg/kg daily for 90 days did not produce any significant toxic effects.{{cite journal | doi=10.1177/1091581816655303 | title=Toxicological Evaluation of β-Caryophyllene Oil | year=2016 | last1=Schmitt | first1=D. | last2=Levy | first2=R. | last3=Carroll | first3=B. | journal=International Journal of Toxicology | volume=35 | issue=5 | pages=558–567 | pmid=27358239 | s2cid=206689471 | doi-access=free }} Caryophyllene has an {{LD50}} of 5,000 mg/kg in mice.{{Cite web |title=β-Caryophyllene - SDS |url=https://www.sigmaaldrich.com/AU/en/sds/ALDRICH/W225207?userType=undefined |access-date=18 April 2024}}{{Cite web |title=Oil of cinnamon - SDS |url=https://www.carlroth.com/medias/SDB-A432-AU-EN.pdf?context=bWFzdGVyfHNlY3VyaXR5RGF0YXNoZWV0c3wyNzQzMDV8YXBwbGljYXRpb24vcGRmfHNlY3VyaXR5RGF0YXNoZWV0cy9oOWMvaDAyLzkwMjM0NDcyNjk0MDYucGRmfGI0MTk3NmNjN2U0Yjg4NjU2NWNmYWY2YWRkMTQzNjM0OWQxNGYxMmU2N2NlYzMyMTY0ZjljZWQ5YzRhM2YzYmY |access-date=18 April 2024}}

14-Hydroxycaryophyllene oxide (C₁₅H₂₄O₂) was isolated from the urine of rabbits treated with (−)-caryophyllene (C₁₅H₂₄). The X-ray crystal structure of 14-hydroxycaryophyllene (as its acetate derivative) has been reported.

{{Unbulleted list citebundle

|{{*}} {{cite journal |last1=Asakawa |first1=Y. |last2=Taira |first2=Z. |last3=Takemoto |first3=T. |last4=Ishida |first4=T. |last5=Kido |first5=M. |last6=Ichikawa |first6=Y. |title=X-Ray Crystal Structure Analysis of 14-Hydroxycaryophyllene Oxide, a New Metabolite of (—)-Caryophyllene, in Rabbits |journal=Journal of Pharmaceutical Sciences |date=June 1981 |volume=70 |issue=6 |pages=710–711 |doi=10.1002/jps.2600700642 |language=en | pmid=7252830 | s2cid=38358882}}

|{{*}} {{cite journal | last1=Adams | first1=T.B. | last2=Gavin | first2=C. Lucas | last3=McGowen | first3=M.M. | last4=Waddell | first4=W.J. | last5=Cohen | first5=S.M. | last6=Feron | first6=V.J. | last7=Marnett | first7=L.J. | last8=Munro | first8=I.C. | last9=Portoghese | first9=P.S. | last10=Rietjens | first10=I.M.C.M. | last11=Smith | first11=R.L. | title=The FEMA GRAS assessment of aliphatic and aromatic terpene hydrocarbons used as flavor ingredients | journal=Food and Chemical Toxicology | publisher=Elsevier BV | volume=49 | issue=10 | year=2011 | issn=0278-6915 | doi=10.1016/j.fct.2011.06.011 | pages=2471–2494 | s2cid=207734236 | pmid=21726592}}

|{{*}} {{cite journal | year=2005 | volume=2 | issue=5 | last=Ishida | first=Takashi | publisher=John Wiley & Sons, Inc (Swiss Chemical Society) | pages=569–590 | s2cid=22213646 | pmid=17192005 | doi=10.1002/cbdv.200590038 | journal= Chemistry & Biodiversity | issn=1612-1872 | title=Biotransformation of Terpenoids by Mammals, Microorganisms, and Plant-Cultured Cells}}

}}

The metabolism of caryophyllene progresses through (−)-caryophyllene oxide (C₁₅H₂₄O) since the latter compound also afforded 14-hydroxycaryophyllene (C₁₅H₂₄O) as a metabolite.{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/1742210#section=Top|title=Caryophyllene oxide – C₁₅H₂₄O |website=PubChem|access-date=September 8, 2016}}

:Caryophyllene (C₁₅H₂₄) → caryophyllene oxide (C₁₅H₂₄O) → 14-hydroxycaryophyllene (C₁₅H₂₄O) → 14-hydroxycaryophyllene oxide (C₁₅H₂₄O₂).

Caryophyllene oxide,{{cite journal |last1=Yang |first1=Depo |last2=Michel |first2=Laura |last3=Chaumont |first3=Jean-Pierre |last4=Millet-Clerc |first4=Joëlle |title=Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis |journal=Mycopathologia |date=1999 |volume=148 |issue=2 |pages=79–82 |doi=10.1023/a:1007178924408 |pmid=11189747 |s2cid=24242933 }} in which the alkene group of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs{{cite journal |last1=Russo |first1=Ethan B |title=Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects: Phytocannabinoid-terpenoid entourage effects |journal=British Journal of Pharmacology |date=August 2011 |volume=163 |issue=7 |pages=1344–1364 |doi=10.1111/j.1476-5381.2011.01238.x |pmid=21749363 |pmc=3165946 }}{{cite journal | last1 = Stahl | first1 = E. | last2 = Kunde | first2 = R. | year = 1973 | title = Die Leitsubstanzen der Haschisch-Suchhunde | trans-title = The tracing substances of hashish search dogs | language = de | journal = Kriminalistik | volume = 27 | pages = 385–389 }} and is also an approved food additive, often as flavoring. Caryophyllene oxide may have negligible cannabinoid activity.{{cite journal |last1=Wiley |first1=Jenny L. |last2=Marusich |first2=Julie A. |last3=Blough |first3=Bruce E. |last4=Namjoshi |first4=Ojas |last5=Brackeen |first5=Marcus |last6=Akinfiresoye |first6=Luli R. |last7=Walker |first7=Teneille D. |last8=Prioleau |first8=Cassandra |last9=Barrus |first9=Daniel G. |last10=Gamage |first10=Thomas F. |title=Evaluation of cannabimimetic effects of selected minor cannabinoids and Terpenoids in mice |journal=Progress in Neuro-Psychopharmacology and Biological Psychiatry |date=June 2024 |volume=132 |pages=110984 |doi=10.1016/j.pnpbp.2024.110984 |pmid=38417478 |pmc=11015967 |pmc-embargo-date=June 8, 2025 |s2cid=267941924 }}

The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ([ ]):

• Cannabis (Cannabis sativa) [3.8–37.5% of cannabis flower essential oil]{{cite web |first1=V. |last1=Mediavilla |first2=S. |last2=Steinemann |url=http://www.internationalhempassociation.org/jiha/jiha4208.html |title=Essential oil of Cannabis sativa L. strains |publisher=International Hemp Association |access-date=11 July 2008}}
• Black caraway (Carum nigrum) [7.8%]{{cite journal |last1=Singh |first1=G. |last2=Marimuthu |first2=P. |last3=De Heluani |first3=C. S. |last4=Catalan |first4=C. A. |title=Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components |journal=Journal of Agricultural and Food Chemistry |volume=54 |issue=1 |pages=174–181 |date=January 2006 |pmid=16390196 |doi=10.1021/jf0518610 |bibcode=2006JAFC...54..174S |hdl=11336/99544 |hdl-access=free }}
• Cloves (Syzygium aromaticum) [1.7–19.5% of clove bud essential oil]{{cite journal |last1=Alma |first1=M. Hakki |last2=Ertaş |first2=Murat |last3=Nitz |first3=Siegfrie |last4=Kollmannsberger |first4=Hubert |title=Chemical composition and content of essential oil from the bud of cultivated Turkish clove (Syzygium aromaticum L.) |journal=BioResources |date=23 May 2007 |volume=2 |issue=2 |pages=265–269 |doi=10.15376/biores.2.2.265-269 |doi-access=free }}
• Hops (Humulus lupulus){{cite journal |last1=Wang |first1=Guodong |last2=Tian |first2=Li |last3=Aziz |first3=Naveed |last4=Broun |first4=Pierre |last5=Dai |first5=Xinbin |last6=He |first6=Ji |last7=King |first7=Andrew |last8=Zhao |first8=Patrick X. |last9=Dixon |first9=Richard A. |title=Terpene Biosynthesis in Glandular Trichomes of Hop |journal=Plant Physiology |date=6 November 2008 |volume=148 |issue=3 |pages=1254–1266 |doi=10.1104/pp.108.125187 |pmid=18775972 |pmc=2577278 }} [5.1–14.5%]{{cite journal|last1=Bernotienë|first1=G.|last2=Nivinskienë|first2=O.|last3=Butkienë|first3=R.|last4=Mockutë|first4=D.|year=2004|title=Chemical composition of essential oils of hops (Humulus lupulus L.) growing wild in Auktaitija|journal=Chemija|volume=4|series=2|pages=31–36|url=http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|access-date=September 6, 2010|archive-date=March 7, 2023|archive-url=https://web.archive.org/web/20230307193722/http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf|url-status=dead}}
• Basil (Ocimum spp.){{cite journal |last1=Zheljazkov |first1=V. D. |last2=Cantrell |first2=C. L. |last3=Tekwani |first3=B. |last4=Khan |first4=S. I. |title=Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting |journal=Journal of Agricultural and Food Chemistry |volume=56 |issue=2 |pages=380–5 |date=January 2008 |pmid=18095647 |doi=10.1021/jf0725629 |bibcode=2008JAFC...56..380Z }} [5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum]{{cite journal |last1=Vasconcelos Silva |first1=M. G. |last2=Abreu Matos |first2=F. J. |last3=Oliveira Lopes |first3=P. R. |last4=Oliveira Silva |first4=F. |last5=Tavares Holanda |first5=M. |editor1-first=G. M. |editor1-last=Cragg |editor2-first=V. S. |editor2-last=Bolzani|editor-link2=Vanderlan da Silva Bolzani |editor3-first=G. S. R. S. |editor3-last=Rao |date=August 2, 2004 |title=Composition of essential oils from three Ocimum species obtained by steam and microwave distillation and supercritical CO₂ extraction |journal=Arkivoc |volume=2004 |issue=6 |pages=66–71 |doi=10.3998/ark.5550190.0005.609 |doi-access=free |hdl=2027/spo.5550190.0005.609 |hdl-access=free }}
• Oregano (Origanum vulgare){{cite journal |vauthors=Harvala C, Menounos P, Argyriadou N |title=Essential oil from Origanum dictamnus |journal=Planta Medica |volume=53 |issue=1 |pages=107–109 |date=February 1987 |pmid=17268981 |doi=10.1055/s-2006-962640 |s2cid=260278580 }} [4.9–15.7%]{{cite journal |last1=Calvo Irabién |first1=L. M. |last2=Yam-Puc |first2=J. A. |last3=Dzib |first3=G. |last4=Escalante Erosa |first4=F. |last5=Peña Rodríguez |first5=L. M. |date=July 2009 |title=Effect of postharvest drying on the composition of Mexican oregano (Lippia graveolens) essential oil |journal=Journal of Herbs, Spices & Medicinal Plants |volume=15 |issue=3 |pages=281–287 |doi=10.1080/10496470903379001 |s2cid=86208062 }}{{cite journal | pmid = 11336262 | volume=57 | issue=1 | title=The essential oil of Origanum vulgare L. ssp. vulgare growing wild in Vilnius district (Lithuania) | date=May 2001 | journal=Phytochemistry | pages=65–69 | doi=10.1016/s0031-9422(00)00474-x| last1=Mockutė | first1=D. | last2=Bernotienė | first2=G. | last3=Judžentienė | first3=A. | bibcode=2001PChem..57...65M }}
• Black pepper (Piper nigrum) [7.29%]
• Lavender (Lavandula angustifolia) [4.62–7.55% of lavender oil]{{cite journal | last1 = Prashar | first1 = A. | last2 = Locke | first2 = I. C. | last3 = Evans | first3 = C. S. | year = 2004 | title = Cytotoxicity of lavender oil and its major components to human skin cells | journal = Cell Proliferation | volume = 37 | issue = 3| pages = 221–229 | doi=10.1111/j.1365-2184.2004.00307.x | pmid=15144499| pmc = 6496511 }}{{cite journal|last1=Umezu|first1=T.|last2=Nagano|first2=K.|last3=Ito|first3=H.|last4=Kosakai|first4=K.|last5=Sakaniwa|first5=M.|last6=Morita|first6=M.|title=Anticonflict effects of lavender oil and identification of its active constituents|journal=Pharmacology Biochemistry and Behavior|date=December 2006|volume=85|issue=4|pages=713–721|doi=10.1016/j.pbb.2006.10.026|pmid=17173962|s2cid=21779233}}
• Rosemary (Rosmarinus officinalis){{cite journal |last1=Ormeño |first1=E. |last2=Baldy |first2=V. |last3=Ballini |first3=C. |last4=Fernández |first4=C. |title=Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients |journal=Journal of Chemical Ecology |volume=34 |issue=9 |pages=1219–1229 |date=September 2008 |pmid=18670820 |doi=10.1007/s10886-008-9515-2 |bibcode=2008JCEco..34.1219O |s2cid=28717342 }} [0.1–8.3%]{{citation needed|date=May 2019}}
• True cinnamon (Cinnamomum verum) [6.9–11.1%]{{cite journal |last1=Kaul |first1=Pran N |last2=Bhattacharya |first2=Arun K |last3=Rajeswara Rao |first3=Bhaskaruni R |last4=Syamasundar |first4=Kodakandla V |last5=Ramesh |first5=Srinivasaiyer |title=Volatile constituents of essential oils isolated from different parts of cinnamon (Cinnamomum zeylanicum Blume) |journal=Journal of the Science of Food and Agriculture |date=1 January 2003 |volume=83 |issue=1 |pages=53–55 |doi=10.1002/jsfa.1277 |bibcode=2003JSFA...83...53K }}
• Malabathrum (Cinnamomum tamala) [25.3%]{{cite journal |last1=Ahmed |first1=Aftab |last2=Choudhary |first2=M. Iqbal |last3=Farooq |first3=Afgan |last4=Demirci |first4=Betül |last5=Demirci |first5=Fatih |last6=Başer |first6=K. Hüsnü Can |title=Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm |journal=Flavour and Fragrance Journal |date=2000 |volume=15 |issue=6 |pages=388–390 |doi=10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F |doi-access=free }}
• Ylang-ylang (Cananga odorata) [3.1–10.7%]
• Copaiba oil (Copaifera){{cite journal |last1=Leandro |first1=Lidiam Maia |last2=de Sousa Vargas |first2=Fabiano |last3=Barbosa |first3=Paula Cristina Souza |last4=Neves |first4=Jamilly Kelly Oliveira |last5=da Silva |first5=José Alexsandro |last6=da Veiga-Junior |first6=Valdir Florêncio |title=Chemistry and Biological Activities of Terpenoids from Copaiba (Copaifera spp.) Oleoresins |journal=Molecules |date=30 March 2012 |volume=17 |issue=4 |pages=3866–3889 |doi=10.3390/molecules17043866 |pmid=22466849 |pmc=6269112 |doi-access=free }}{{cite journal |last1=Sousa |first1=João Paulo B. |last2=Brancalion |first2=Ana P.S. |last3=Souza |first3=Ariana B. |last4=Turatti |first4=Izabel C.C. |last5=Ambrósio |first5=Sérgio R. |last6=Furtado |first6=Niege A.J.C. |last7=Lopes |first7=Norberto P. |last8=Bastos |first8=Jairo K. |title=Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils |journal=Journal of Pharmaceutical and Biomedical Analysis |date=March 2011 |volume=54 |issue=4 |pages=653–659 |doi=10.1016/j.jpba.2010.10.006 |pmid=21095089 |doi-access=free }}

Caryophyllene is a common sesquiterpene among plant species. It is biosynthesized from the common terpene precursors dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). First, single units of DMAPP and IPP are reacted via an S_N1-type reaction with the loss of pyrophosphate, catalyzed by the enzyme GPPS2, to form geranyl pyrophosphate (GPP). This further reacts with a second unit of IPP, also via an S_N1-type reaction catalyzed by the enzyme IspA, to form farnesyl pyrophosphate (FPP). Finally, FPP undergoes QHS1 enzyme-catalyzed intramolecular cyclization to form caryophyllene.{{cite journal |last1=Yang |first1=Jianming |last2=Li |first2=Zhengfeng |last3=Guo |first3=Lizhong |last4=Du |first4=Juan |last5=Bae |first5=Hyeun-Jong |title=Biosynthesis of β-caryophyllene, a novel terpene-based high-density biofuel precursor, using engineered Escherichia coli |journal=Renewable Energy |date=December 2016 |volume=99 |pages=216–223 |doi=10.1016/j.renene.2016.06.061 |bibcode=2016REne...99..216Y }}

:File:Wiki Project - Caryophyllene 1.svg{{clear-left}}

• Food Chemicals Codex{{cite web

|last=The United States Pharmacopeial Convention

|title=Revisions to FCC, First Supplement

|url=http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html

|access-date=29 June 2009

|url-status=dead

|archive-url=https://web.archive.org/web/20100705122159/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html

|archive-date=5 July 2010

}}{{cite web

| author = Therapeutic Goods Administration

| title = Chemical substances

| url = http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf

| access-date = 29 June 2009

| archive-url = https://web.archive.org/web/20110422122647/http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf

| archive-date = 22 April 2011

| url-status = dead

| author-link = Therapeutic Goods Administration

}}

• {{cite journal |last1=Ghelardini |first1=C. |last2=Galeotti |first2=N. |last3=Di Cesare Mannelli |first3=L. |last4=Mazzanti |first4=G. |last5=Bartolini |first5=A. |title=Local anaesthetic activity of beta-caryophyllene |journal=Farmaco |volume=56 |issue=5–7 |pages=387–389 |year=2001 |pmid=11482764 |doi= 10.1016/S0014-827X(01)01092-8|hdl=2158/397975 |hdl-access=free }}

{{Reflist|2}}

{{Cannabinoids}}

{{Cannabinoidergics}}

{{Authority control}}

Category:Flavors

Category:Cannabinoids

Category:Sesquiterpenes

Category:Alkene derivatives

Category:Hydrocarbons

Category:CB2 receptor agonists

Category:Cyclobutanes

Category:Bicyclic compounds