Cannabichromene

Source: Wikipedia, the free encyclopedia.
Cannabichromene
Names
IUPAC name
2-Methyl-2-(4-methylpent-3-enyl)-7-pentyl-5-chromenol
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.236.929 Edit this at Wikidata
UNII
  • InChI=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 ☒N
    Key: UVOLYTDXHDXWJU-UHFFFAOYSA-N ☒N
  • 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
    Key: UVOLYTDXHDXWJU-UHFFFAOYAG
  • CCCCCC1=CC2=C(C=CC(O2)(C)CCC=C(C)C)C(=C1)O
Properties
C21H30O2
Molar mass 314.469 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cannabichromene (CBC), also called cannabichrome, cannanbichromene, pentylcannabichromene or cannabinochromene,[1] exhibits anti-inflammatory properties in vitro, which may, theoretically, contribute to cannabis analgesic effects.[2] It is a

phytocannabinoid, one of the hundreds of cannabinoids found in the Cannabis plant.[3] It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.[3][4] CBC and cannabinols are present in cannabis.[3] It is not scheduled by the Convention on Psychotropic Substances
.

Biosynthesis

Within 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 above 93 °C, CBCA is decarboxylated, producing CBC. See also the biosynthetic scheme image below.[citation needed]

CBC biosynthetic scheme

Pharmacology

Cannabichromene has been hypothesized to affect THC psychoactivity, though in vivo effects have not been demonstrated.

mouse model.[8]

stereoisomers
.

References

  1. ^ "Cannabichromene". PubChem. National Center for Biotechnology Information. 16 February 2019. Retrieved 12 February 2019.
  2. PMID 28120232
    .
  3. ^
    PMID 28120231
    .
  4. PMID 26836472
    .
  5. S2CID 827221
    .
  6. ^ "What Is CBC (Cannabichromene)?". CNBS. Retrieved 2019-03-31.
  7. S2CID 1341744
    .
  8. PMID 33395525
  9. ^
    PMID 33230154
    .
  10. PMID 25311884
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Cannabichromene&oldid=1186273228"