Cannabinol

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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)

Cannabinol (CBN) is a mildly psychoactive cannabinoid that binds to the cannabinoid receptors with more selectivity for CB2 over CB1[5][6][7] found in trace amounts from Cannabis.[8] CBN is mostly found in cannabis that is aged and stored, and is derived from the plant's main psychoactive chemical, tetrahydrocannabinol (THC).[9][10]

It was the first cannabis compound to be isolated from cannabis extract in the late 1800s. Its structure and chemical synthesis were achieved by 1940.[11]

Formation

Delta-9-THC can degrade into CBN from oxidation.[12][13]

Pharmacology

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.[14][15][7] Both THC and CBN activate the CB1 (Ki = 211.2 nM) and CB2 (Ki = 126.4 nM) receptors.[16] It is metabolised to 11-OH-CBN, which is a more potent CB1 agonist than CBN but acts as a weak antagonist at CB2.[17]

Chemistry

In contrast to THC, CBN has no double bond isomers nor stereoisomers.

CBN can degrade into HU-345 from oxidation.[18]

Legal status

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,[19] so the signatory countries to these international drug control treaties are not required by these treaties to control CBN.

United States

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,[20][21][22] and sales or possession of CBN could potentially be prosecuted under the Federal Analogue Act.[23] 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.[24]

References

  1. ^ Cannabinol in the ChemIDplus database.
  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 2016-05-22.
  5. ^ Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, et al. (September 1997). "Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase". Journal of Medicinal Chemistry. 40 (20): 3228–3233. doi:10.1021/jm970126f. PMID 9379442.
  6. ^ Sampson PB (January 2021). "Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the "Big Two"". Journal of Natural Products. 84 (1): 142–160. doi:10.1021/acs.jnatprod.0c00965. PMID 33356248. S2CID 229694293.
  7. ^ a b "Cannabinol (Code C84510)". NCI Thesaurus. National Cancer Institute, National Institutes of Health, U.S. Department of Health and Human Services.
  8. ^ Morales P, Hurst DP, Reggio PH (2017). "Molecular Targets of the Phytocannabinoids: A Complex Picture". Progress in the Chemistry of Organic Natural Products. 103: 103–131. doi:10.1007/978-3-319-45541-9_4. ISBN 978-3-319-45539-6. PMC 5345356. PMID 28120232.
  9. ^ Kroner GM, Johnson-Davis KL, Doyle K, McMillin GA (May 2020). "Cannabinol (CBN) Cross-Reacts with Two Urine Immunoassays Designed to Detect Tetrahydrocannabinol (THC) Metabolite". The Journal of Applied Laboratory Medicine. 5 (3): 569–574. doi:10.1093/jalm/jfaa020. PMID 32445358.
  10. ^ Andre CM, Hausman JF, Guerriero G (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. PMC 4740396. PMID 26870049.
  11. ^ 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. Cannabinol (CBN; Figure 1), much of which is thought to be formed from THC during the storage of harvested cannabis, was the first of the plant cannabinoids (phytocannabinoids) to be isolated, from a red oil extract of cannabis, at the end of the 19th century. Its structure was elucidated in the early 1930s by R.S. Cahn, and its chemical synthesis first achieved in 1940 in the laboratories of R. Adams in the U.S.A. and Lord Todd in the U.K.
  12. ^ Garrett ER, Gouyette AJ, Roseboom H (January 1978). "Stability of tetrahydrocannabinols II". Journal of Pharmaceutical Sciences. 67 (1): 27–32. doi:10.1002/jps.2600670108. PMID 22740.
  13. ^ Russo EB, Marcu J (2017). "Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads". In Kendall D, Alexander SP (eds.). Cannabinoid Pharmacology. Advances in Pharmacology (San Diego, Calif.). Vol. 80. pp. 67–134 (79). doi:10.1016/bs.apha.2017.03.004. ISBN 978-0-12-811233-5. PMID 28826544. Cannabinol (CBN) is the nonenzymatic oxidation byproduct of THC and is most commonly an artifact found after prolonged storage, especially at higher temperatures. CBN was the first cannabinoid to be identified and isolated from cannabis (Wood, Spivey, & Easterfield, 1899)
  14. ^ 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): 3778–3785. doi:10.1021/jm0001572. PMID 11020293.
  15. ^ 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–PL6. doi:10.1016/S0024-3205(98)00238-0. PMID 9667767.
  16. ^ Russo EB, Marcu J (2017). "Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads". Cannabinoid Pharmacology. Advances in Pharmacology. Vol. 80. pp. 67–134. doi:10.1016/bs.apha.2017.03.004. ISBN 978-0-12-811232-8. PMID 28826544.
  17. ^ Rhee MH, Vogel Z, Barg J, Bayewitch M, Levy R, Hanus L, et al. (September 1997). "Cannabinol derivatives: binding to cannabinoid receptors and inhibition of adenylylcyclase". Journal of Medicinal Chemistry. 40 (20): 3228–3233. doi:10.1021/jm970126f. PMID 9379442.
  18. ^ Kogan NM, Peters M, Mechoulam R (March 2021). "Cannabinoid Quinones-A Review and Novel Observations". Molecules. 26 (6): 1761. doi:10.3390/molecules26061761. PMC 8003933. PMID 33801057.
  19. ^ "UN International Drug Control Conventions". United Nations Office on Drugs and Crime. United Nations Commision on Narcotic Drugs.
  20. ^ 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.
  21. ^ Mead A (May 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.
  22. ^ "Section 1308.11 Schedule I". Code of Federal Regulations. Office of Diversion Control, Drug Enforcement Administration, U.S. Department of Justice. Archived from the original on 9 February 2012.
  23. ^ "Federal Controlled Substance Analogue Act Summary". Erowid Analog Law Vault. January 2001.
  24. ^ "Establishment of a New Drug Code for Marihuana Extract" (PDF). Federal Register. 81 (240). 14 December 2016.

External links

  • Erowid Compounds found in Cannabis sativa

Notes

This article is a direct transclusion of the Wikipedia article and therefore may not meet the same editing standards as CannabisQAwiki.