| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-18 23:23:57 UTC |
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| Updated at | 2020-12-07 19:07:04 UTC |
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| CannabisDB ID | CDB000078 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | beta-Caryophyllene |
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| Description | beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene. 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. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature. It is barely soluble in water and soluble in alcohol and propylene glycol. beta-Caryophyllene, a promising precursor for the production of high density fuels, has been biosynthesized in E.coli from the common terpene precursors dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). First, single units of DMAPP and IPP are reacted via a substitution, nucleophilic (SN)1-type reaction with the loss of pyrophosphate, catalyzed by the enzyme geranyl diphosphate synthetase (GPPS2), to form geranyl pyrophosphate (GPP). This further reacts with a second unit of IPP, also via an SN1-type reaction catalyzed by the enzyme farnesyl diphospahe synthetase (IspA), to form farnesyl pyrophosphate (FPP). Finally, FPP undergoes beta-caryophyllene synthase -catalyzed intramolecular cyclization to form caryophyllene ( Ref:DOI ). It is an abundant constituent of many essential oils including that of Syzygium aromaticum (clove bud, up to 19%; ), Cannabis sativa flower (up to 37%; Ref:DOI PMID: 6991645 ), rosemary, and hops. beta-Caryophyllene is also found in cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. Beta-caryophyllene is a major sesquiterpene of various plant essential oils that reportedly has antioxidant, anti-inflammatory (PMID: 24484210 ), anticancer (PMID: 27696789 ), cardioprotective (PMID: 30343038 ), hepatoprotective, gastroprotective, nephroprotective, antimicrobial, immune-modulatory activity and neuroprotective effects. It has a role in alleviating pain, anxiety, spasm, convulsion, depression, alcoholism, and Alzheimer's disease and may mediates these effects through interactions with the cannabinoid receptors (CR), especially CBR2 (PMID: 30281175 ; PMID: 18574142 ). |
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| Structure | |
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| Synonyms | Not Available |
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| Chemical Formula | C15H24 |
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| Average Molecular Weight | 204.36 |
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| Monoisotopic Molecular Weight | 204.1878 |
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| IUPAC Name | (1S,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene |
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| Traditional Name | (1S,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene |
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| CAS Registry Number | 87-44-5 |
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| SMILES | C\C1=C\CCC(=C)[C@H]2CC(C)(C)[C@H]2CC1 |
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| InChI Identifier | InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14+/m1/s1 |
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| InChI Key | NPNUFJAVOOONJE-FGHOCRGKSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Sesquiterpenoids |
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| Direct Parent | Sesquiterpenoids |
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| Alternative Parents | |
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| Substituents | - Caryophyllane sesquiterpenoid
- Sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Role | Biological role: Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | Not Available |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available | 2020-06-30 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available | 2020-06-30 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | Not Available |
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| Transporters | Not Available |
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| Metal Bindings | Not Available |
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| Receptors | |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| 8-Ball Kush | Detected and Quantified | 2.961 mg/g dry wt | | details | | 9 Lb Hammer | Detected and Quantified | 2.679 mg/g dry wt | | details | | 97 Sage | Detected and Quantified | 1.247 mg/g dry wt | | details | | Adonis | Detected and Quantified | 4.516 mg/g dry wt | | details | | Alien Sour Apple | Detected and Quantified | 1.726 mg/g dry wt | | details | | Animal Cookies | Detected and Quantified | 6.8 +/- 1 mg/g dry wt | | details | | Black Boss | Detected and Quantified | 1.716 mg/g dry wt | | details | | Blue Cookies | Detected and Quantified | 6 +/- 0.6 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 3.184 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 3.277 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 3.324 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 2.3 +/- 0.6 mg/g dry wt | | details | | Bob Marley | Detected and Quantified | 0.709 mg/g dry wt | | details | | Bubba Kush | Detected and Quantified | 4.1 +/- 1.9 mg/g dry wt | | details | | Chemdawg | Detected and Quantified | 4.756 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 4.307 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 11.124 mg/g dry wt | | details | | Chemdog | Detected and Quantified | 6.4 +/- 1.8 mg/g dry wt | | details | | Cookies and Cream | Detected and Quantified | 2.685 mg/g dry wt | | details | | Cosmic Lotus | Detected and Quantified | 1.596 mg/g dry wt | | details | | Crown Og | Detected and Quantified | 2.7 +/- 0.8 mg/g dry wt | | details | | Dairy Queen | Detected and Quantified | 0.806 mg/g dry wt | | details | | Dark Shadow Haze | Detected and Quantified | 1.992 mg/g dry wt | | details | | FLO | Detected and Quantified | 1.924 mg/g dry wt | | details | | Fortune Cookies | Detected and Quantified | 8.2 +/- 1.9 mg/g dry wt | | details | | Gas | Detected and Quantified | 4 +/- 0.6 mg/g dry wt | | details | | Gelato | Detected and Quantified | 2.1 +/- 1.4 mg/g dry wt | | details | | Girl Scout Cookies | Detected and Quantified | 6.7 +/- 1.3 mg/g dry wt | | details | | Godfather | Detected and Quantified | 1.6 +/- 0.3 mg/g dry wt | | details | | Goji OG | Detected and Quantified | 2.329 mg/g dry wt | | details | | Golden Cobra | Detected and Quantified | 2.195 mg/g dry wt | | details | | Golden Sage | Detected and Quantified | 2.194 mg/g dry wt | | details | | Gorilla Glue | Detected and Quantified | 8.169 mg/g dry wt | | details | | Gorilla Glue #4 | Detected and Quantified | 5.811 mg/g dry wt | | details | | Gorilla Glue #4 | Detected and Quantified | 7.8 +/- 1.5 mg/g dry wt | | details | | Grape Ape | Detected and Quantified | 3.5 +/- 0.5 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 2.423 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 2.571 mg/g dry wt | | details | | Grizzly Kush | Detected and Quantified | 1.608 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 2.295 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 3.201 mg/g dry wt | | details | | Hemlock | Detected and Quantified | 1.592 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 3.415 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 5.599 mg/g dry wt | | details | | Jack Herer | Detected and Quantified | 1.16 mg/g dry wt | | details | | Jack Herer | Detected and Quantified | 2.6 +/- 0.7 mg/g dry wt | | details | | Jack Herer | Detected and Quantified | 1.160 mg/g dry wt | | details | | Kandy Kush | Detected and Quantified | 1.645 mg/g dry wt | | details | | Kush Puppy | Detected and Quantified | 1.624 mg/g dry wt | | details | | La Choco | Detected and Quantified | 2.616 mg/g dry wt | | details | | Lemon Balm | Detected and Quantified | 2.224 mg/g dry wt | | details | | Lemon Goji | Detected and Quantified | 1.309 mg/g dry wt | | details | | Lemon OG | Detected and Quantified | 0.937 mg/g dry wt | | details | | Lemon Sherbet | Detected and Quantified | 8.528 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.883 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 5.628 mg/g dry wt | | details | | Liberty Haze | Detected and Quantified | 1.491 mg/g dry wt | | details | | Lohan | Detected and Quantified | 1.126 mg/g dry wt | | details | | Lucky Charms | Detected and Quantified | 4.039 mg/g dry wt | | details | | Master Kush | Detected and Quantified | 2.7 +/- 0.5 mg/g dry wt | | details | | Maui Haze | Detected and Quantified | 7.402 mg/g dry wt | | details | | Miami White Kush | Detected and Quantified | 6.8 +/- 0.9 mg/g dry wt | | details | | Moby Dick | Detected and Quantified | 3.223 mg/g dry wt | | details | | Moonshine Ghost Trane Haze | Detected and Quantified | 2.667 mg/g dry wt | | details | | Mr. Nice | Detected and Quantified | 3 +/- 1.4 mg/g dry wt | | details | | Nightmare Cookie | Detected and Quantified | 4.698 mg/g dry wt | | details | | Og Kush | Detected and Quantified | 4 +/- 1.1 mg/g dry wt | | details | | Orange Skunk | Detected and Quantified | 5.263 mg/g dry wt | | details | | Pineapple Skunk | Detected and Quantified | 3.159 mg/g dry wt | | details | | Pipe Dream | Detected and Quantified | 4.078 mg/g dry wt | | details | | Platinum Delight | Detected and Quantified | 3.524 mg/g dry wt | | details | | Purple Cream | Detected and Quantified | 3.7 +/- 0.9 mg/g dry wt | | details | | Purple Eclipse | Detected and Quantified | 4.26 mg/g dry wt | | details | | Purple Eclipse | Detected and Quantified | 4.260 mg/g dry wt | | details | | Purple Princess | Detected and Quantified | 4.1 +/- 1.2 mg/g dry wt | | details | | Purple Urkle | Detected and Quantified | 3.5 +/- 0.5 mg/g dry wt | | details | | Rocket Fuel | Detected and Quantified | 4.702 mg/g dry wt | | details | | Rollex OG | Detected and Quantified | 2.286 mg/g dry wt | | details | | Rosetta Stone | Detected and Quantified | 3.331 mg/g dry wt | | details | | Satori | Detected and Quantified | 0.537 mg/g dry wt | | details | | Sherbert | Detected and Quantified | 6.4 +/- 2 mg/g dry wt | | details | | Skunk Haze | Detected and Quantified | 4.225 mg/g dry wt | | details | | Skywalker OG | Detected and Quantified | 2.81 mg/g dry wt | | details | | Skywalker OG | Detected and Quantified | 2.810 mg/g dry wt | | details | | Skywalker Og Kush | Detected and Quantified | 3.7 +/- 0.9 mg/g dry wt | | details | | Sour Diesel | Detected and Quantified | 4 +/- 1.3 mg/g dry wt | | details | | Spectrum | Detected and Quantified | 1.729 mg/g dry wt | | details | | Star Bud | Detected and Quantified | 2.893 mg/g dry wt | | details | | Star Killer | Detected and Quantified | 2.591 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 2.185 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 2.416 mg/g dry wt | | details | | Strawberry Haze | Detected and Quantified | 2.7 +/- 0.5 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 4.199 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 4.745 mg/g dry wt | | details | | Superman Og Kush | Detected and Quantified | 3.5 +/- 0.5 mg/g dry wt | | details | | Tahoe Og Kush | Detected and Quantified | 4.6 +/- 0.8 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 2.371 mg/g dry wt | | details | | The Sauce | Detected and Quantified | 6.159 mg/g dry wt | | details | | Thin Mints | Detected and Quantified | 7.1 +/- 2.5 mg/g dry wt | | details | | Trainwreck | Detected and Quantified | 1.5 +/- 0.4 mg/g dry wt | | details | | Triple O | Detected and Quantified | 3.5 +/- 0.5 mg/g dry wt | | details | | Venom OG | Detected and Quantified | 4.853 mg/g dry wt | | details | | White Widow | Detected and Quantified | 1.198 mg/g dry wt | | details | | Wonder Woman | Detected and Quantified | 1.913 mg/g dry wt | | details |
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| External Links |
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| HMDB ID | Not Available |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | Not Available |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | Not Available |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Not Available |
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| METLIN ID | Not Available |
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| PubChem Compound | 5498518 |
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| PDB ID | Not Available |
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| ChEBI ID | Not Available |
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| References |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- Sain S, Naoghare PK, Devi SS, Daiwile A, Krishnamurthi K, Arrigo P, Chakrabarti T: Beta caryophyllene and caryophyllene oxide, isolated from Aegle marmelos, as the potent anti-inflammatory agents against lymphoma and neuroblastoma cells. Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):45-55. doi: 10.2174/18715230113129990016. [PubMed:24484210 ]
- Fidyt K, Fiedorowicz A, Strzadala L, Szumny A: beta-caryophyllene and beta-caryophyllene oxide-natural compounds of anticancer and analgesic properties. Cancer Med. 2016 Oct;5(10):3007-3017. doi: 10.1002/cam4.816. Epub 2016 Sep 30. [PubMed:27696789 ]
- Youssef DA, El-Fayoumi HM, Mahmoud MF: Beta-caryophyllene protects against diet-induced dyslipidemia and vascular inflammation in rats: Involvement of CB2 and PPAR-gamma receptors. Chem Biol Interact. 2019 Jan 5;297:16-24. doi: 10.1016/j.cbi.2018.10.010. Epub 2018 Oct 19. [PubMed:30343038 ]
- Machado KDC, Islam MT, Ali ES, Rouf R, Uddin SJ, Dev S, Shilpi JA, Shill MC, Reza HM, Das AK, Shaw S, Mubarak MS, Mishra SK, Melo-Cavalcante AAC: A systematic review on the neuroprotective perspectives of beta-caryophyllene. Phytother Res. 2018 Dec;32(12):2376-2388. doi: 10.1002/ptr.6199. Epub 2018 Oct 3. [PubMed:30281175 ]
- Gertsch J, Leonti M, Raduner S, Racz I, Chen JZ, Xie XQ, Altmann KH, Karsak M, Zimmer A: Beta-caryophyllene is a dietary cannabinoid. Proc Natl Acad Sci U S A. 2008 Jul 1;105(26):9099-104. doi: 10.1073/pnas.0803601105. Epub 2008 Jun 23. [PubMed:18574142 ]
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