| 词条 | Cannabichromene |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 409743007 | ImageFile=(RS)-Cannabichromene.svg | IUPACName=2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol | OtherNames= |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo=20675-51-8 | PubChem=30219 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 422704 | SMILES=CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 28064 | InChI = 1/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3 | InChIKey = UVOLYTDXHDXWJU-UHFFFAOYAG | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = UVOLYTDXHDXWJU-UHFFFAOYSA-N |Section2={{Chembox Properties | C=21 | H=30 | O=2 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }}Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,[1] is one of the 120 cannabinoids found in the Cannabis plant,[2] and is therefore a phytocannabinoid. It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.[2][3] Cannabichromene and its derivatives are as abundant as cannabinols in cannabis.[2] It is not active at CB1 or CB2 receptors, but is an agonist of TRPA1 and less potently, an agonist of TRPV3 and TRPV4.[2] CBC has two stereoisomers. It is not scheduled by the Convention on Psychotropic Substances. "A body of literature The National Library of Medicine discusses shows data which recently demonstrated that the major non-THC phytocannabinoid, cannabichromene (CBC), promotes cell survival during differentiation while blunting cell differentiation into astroglia."[4] BiosynthesisWithin the Cannabis plant, CBC occurs mainly as cannabichromenic acid (CBCA, 2-COOH-CBC, CBC-COOH). Geranyl pyrophosphate and olivetolic acid combine to produce cannabigerolic acid (CBGA; the sole intermediate for all other phytocannabinoids), which is cyclized by the enzyme CBCA synthase to form CBCA. Over time, or when heated somewhere above 200° F, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below.{{citation needed|date=January 2018}} {{-}}PharmacologyAs of 2017, CBC is under laboratory research to identify its possible pharmacological properties. No in vivo human studies exist as of 2019.[1][2][5][6] References1. ^1 {{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/cannabichromene|title=Cannabichromene|author= |date=16 February 2019 |website=PubChem |publisher=National Center for Biotechnology Information |access-date=12 February 2019|quote=}} {{Cannabinoids}}{{Transient receptor potential channel modulators}}2. ^1 2 3 4 {{Cite book|pmid=28120231|year=2017|last1=Turner|first1=Sarah E.|first2=Claire M.|last2=Williams|first3=Leslie|last3=Iversen|authorlink3=Leslie Iversen|first4=Benjamin J.|last4=Whalley|chapter=Molecular Pharmacology of Phytocannabinoids|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=Springer International Publishing|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=61–101|doi=10.1007/978-3-319-45541-9_3|isbn=978-3-319-45539-6}} 3. ^{{cite journal | first1 = Oier | last1 = Aizpurua-Olaizola | first2 = Umut | last2 = Soydaner | first3 = Ekin | last3 = Öztürk | first4 = Daniele | last4 = Schibano | first5 = Yilmaz | last5 = Simsir | first6 = Patricia | last6 = Navarro | first7 = Nestor | last7 = Etxebarria | first8 = Aresatz |last8 = Usobiaga | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = Journal of Natural Products | volume = 79 | issue = 2 | pages = 324–331 | year = 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 }} 4. ^{{Cite web|url=https://cbdoilgeek.com/key-properties-of-medical-cannabis/|title=Discussion of Key Properties of Medical Cannabis|last=|first=|date=|website=|archive-url=|archive-date=|dead-url=|access-date=}} 5. ^{{Cite book|pmc=5345356|year=2017|last1=Morales|first1=Paula|first2=Dow P.|last2=Hurst|first3=Patricia H.|last3=Reggio|chapter=Molecular Targets of the Phytocannabinoids: A Complex Picture|title=Phytocannabinoids: Unraveling the Complex Chemistry and Pharmacology of Cannabis sativa|editor1-first=A. Douglas|editor1-last=Kinghorn|editor2-first=Heinz|editor2-last=Falk|editor2-link=Heinz Falk|editor3-first=Simon|editor3-last=Gibbons|editor3-link=Simon Gibbons|editor4-first=Jun'ichi|editor4-last=Kobayashi|publisher=Springer International Publishing|series=Progress in the Chemistry of Organic Natural Products|volume=103|pages=103–131|pmid=28120232|doi=10.1007/978-3-319-45541-9_4|isbn=978-3-319-45539-6}} 6. ^{{Cite journal |pmid = 20619971|pmc = 2967639|year = 2010|last1 = Delong|first1 = G. T.|title = Pharmacological evaluation of the natural constituent of Cannabis sativa, cannabichromene and its modulation by Δ(9)-tetrahydrocannabinol|journal = Drug and Alcohol Dependence|volume = 112|issue = 1–2|pages = 126–33|last2 = Wolf|first2 = C. E.|last3 = Poklis|first3 = A.|last4 = Lichtman|first4 = A. H.|doi = 10.1016/j.drugalcdep.2010.05.019}} 3 : Cannabinoids|Chromenes|Phenols |
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