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Cannabinol

Not to be confused with cannabidiol or cannabinodiol.

Cannabinol
Legal status
Legal status
  • CA: Unscheduled
  • UK: Class B
  • US: Unscheduled
Identifiers
  • 6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.216.772 Edit this at Wikidata
Chemical and physical data
FormulaC21H26O2
Molar mass310.437 g·mol−1
3D model (JSmol)
Melting point76–77 °C (169–171 °F) [1]
Solubility in waterInsoluble in water,[2] soluble in methanol[3] and ethanol[4] mg/mL (20 °C)
  • Oc2cc(cc1OC(c3c(c12)cc(cc3)C)(C)C)CCCCC
  • InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3 checkY
  • Key:VBGLYOIFKLUMQG-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cannabinol (CBN) is a mildly psychoactive cannabinoid (e.g., CBD) that acts as a low affinity partial agonist at both CB1 and CB2 receptors. This activity at CB1 and CB2 receptors constitutes interaction of CBN with the endocannabinoid system (ECS).

In 1896 Cannabinol was first discovered in Cannabis by Thomas Barlow Wood, W.T Newton Spivey, and Thomas Easterfield.[5] In the early 1930s CBNs structure was identified by Robert Sidney Cahn,[6][7] marking the first development of a cannabis extract.

Its chemical synthesis were achieved by 1940, followed by some of the first basic research studies to determine the effects of individual cannabis-derived compounds in vivo. Although CBN shares the same mechanism of action as other phytocannabinoids (e.g., Delta-9-tetrahydrocannabinol, Δ9-THC), it has a lower affinity for CB1 receptors, meaning that much higher doses of CBN are required in order to experience effects, such as mild sedation.

  1. ^ Cannabinol from PubChem
  2. ^ Lide DR (2012). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–90. ISBN 978-1-43988049-4.
  3. ^ "Cannabinol solution, analytical standard, for drug analysis". Sigma-Aldrich. c046.
  4. ^ "Cannabinol" (PDF). Biotrend. Archived from the original (PDF) on May 22, 2016.
  5. ^ Wood TB, Spivey WN, Easterfield III TH (1899). "III.—Cannabinol. Part I". Journal of the Chemical Society, Transactions. 75: 20–36. doi:10.1039/CT8997500020.
  6. ^ Cahn RS (1932). "174. Cannabis indica resin. Part III. The constitution of cannabinol". Journal of the Chemical Society (Resumed): 1342–1353. doi:10.1039/JR9320001342.
  7. ^ Pertwee RG (January 2006). "Cannabinoid pharmacology: the first 66 years". British Journal of Pharmacology. 147 (Suppl 1): S163–S171. doi:10.1038/sj.bjp.0706406. PMC 1760722. PMID 16402100.

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