Cannabinol

Cannabinol (CBN) is a mildly psychoactive cannabinoid found only in trace amounts in Cannabis,[5] and is mostly found in aged Cannabis.[6] Pharmacologically relevant quantities are formed as a metabolite of tetrahydrocannabinol (THC).[7] CBN acts as a partial agonist at the CB1 receptors, but has a higher affinity to CB2 receptors; however, it has lower affinities relative to THC.[8][9][10] Degraded or oxidized cannabis products, such as low-quality baled cannabis and traditionally produced hashish, are high in CBN.[citation needed]

Cannabinol
Cannabinol.svg
Cannabinol 3D.png
Clinical data
Routes of
administration
Oral, inhaled
ATC code
  • none
Legal status
Legal status
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 point77 °C (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)

Unlike other cannabinoids, CBN does not stem directly from cannabigerol (CBG) or cannabigerolic acid (CBGA), but rather is the degraded product of tetrahydrocannabinolic acid (THCA).[citation needed] If cannabis is exposed to air or ultraviolet light (for example, in sunlight) for a prolonged period of time, THCA will convert to cannabinolic acid (CBNA). CBN is then formed by decarboxylation of CBNA.

ChemistryEdit

In contrast to THC, CBN has no double bond isomers nor stereoisomers. Both THC and CBN activate the CB1 and CB2 receptors.[citation needed]

Legal statusEdit

CBN is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971,[11] so the signatory countries to these international drug control treaties are not required by these treaties to control CBN.

United StatesEdit

 
Cannabinol 10 mg transdermal patches sold at marijuana dispensaries in Colorado, U.S.

As of 2021 in the United States, CBN and other cannabis extracts remain illegal under federal law to prescribe for medical use or to use as an ingredient in dietary supplements or other foods,[12][13][14][15] and sales or possession of CBN could potentially be prosecuted under the Federal Analogue Act.[16] In December 2016, the Drug Enforcement Administration added marijuana extracts, which are defined as any "extract containing one or more cannabinoids that has been derived from any plant of the genus Cannabis, other than the separated resin", to Schedule I.[17]

ReferencesEdit

  1. ^ Cannabinol in the ChemIDplus database.
  2. ^ David R. Lide (2012). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–90. ISBN 978-1-43988049-4.
  3. ^ Sigma-Aldrich Co., Cannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis.
  4. ^ Biotrend: Cannabinol Archived 2016-05-22 at the Wayback Machine (PDF: 21 kB)
  5. ^ Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE (1975). "Effects of delta9-tetrahydrocannabinol and cannabinol in man". Pharmacology. 13 (6): 502–12. doi:10.1159/000136944. PMID 1221432.
  6. ^ Andre, Christelle M.; Hausman, Jean-Francois; Guerriero, Gea (2016-02-04). "Cannabis sativa: The Plant of the Thousand and One Molecules". Frontiers in Plant Science. 7: 19. doi:10.3389/fpls.2016.00019. ISSN 1664-462X. PMC 4740396. PMID 26870049.
  7. ^ McCallum ND, Yagen B, Levy S, Mechoulam R (May 1975). "Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol". Experientia. 31 (5): 520–1. doi:10.1007/bf01932433. PMID 1140243. S2CID 29060389.
  8. ^ Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK (October 2000). "Novel cannabinol probes for CB1 and CB2 cannabinoid receptors". Journal of Medicinal Chemistry. 43 (20): 3778–85. doi:10.1021/jm0001572. PMID 11020293.
  9. ^ Petitet F, Jeantaud B, Reibaud M, Imperato A, Dubroeucq MC (1998). "Complex pharmacology of natural cannabinoids: evidence for partial agonist activity of delta9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors". Life Sciences. 63 (1): PL1–6. doi:10.1016/S0024-3205(98)00238-0. PMID 9667767.
  10. ^ "NIA National Cancer Institute; NCIthesaurus". Cannabinol (Code C84510).
  11. ^ UN International Drug Control Conventions
  12. ^ Mead A (2019-06-14). "Legal and Regulatory Issues Governing Cannabis and Cannabis-Derived Products in the United States". Frontiers in Plant Science. 10: 697. doi:10.3389/fpls.2019.00697. PMC 6590107. PMID 31263468.
  13. ^ "FDA Regulation of Cannabis and Cannabis-Derived Products, Including Cannabidiol (CBD)". US Food and Drug Administration (FDA). 1 October 2020. Retrieved 12 January 2021.
  14. ^ Mead, Alice (2017). "The legal status of cannabis (marijuana) and cannabidiol (CBD) under U.S. Law". Epilepsy & Behavior. 70 (Pt B): 288–291. doi:10.1016/j.yebeh.2016.11.021. PMID 28169144.
  15. ^ §1308.11 Schedule I.
  16. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
  17. ^ "Establishment of a New Drug Code for Marihuana Extract" (PDF). Federal Register, Vol. 81, No. 240. December 14, 2016.

External linksEdit

  • Erowid Compounds found in Cannabis sativa