Cannabinol
From Wikipedia, the free encyclopedia
Not to be confused with Cannabidiol.
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| Systematic (IUPAC) name | |
|---|---|
| 6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol | |
| Clinical data | |
| Identifiers | |
521-35-7  |
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| None | |
| PubChem | CID 2543 |
| IUPHAR ligand | 740 |
| ChemSpider | 2447  |
| UNII | 7UYP6MC9GH |
| KEGG | C07580 |
| ChEMBL | CHEMBL74415 |
| Chemical data | |
| Formula | C21H26O2 |
| 310.4319 g/mol | |
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| Physical data | |
| Melting point | 77 °C (171 °F) [4] |
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insoluble in water[1] soluble in methanol[2] and ethanol[3] mg/mL (20 °C) |
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Cannabinol (CBN) is a weak psychoactive cannabinoid found only in trace amounts in Cannabis sativa and Cannabis indica.[5] It is mostly a metabolite of tetrahydrocannabinol (THC).[6] CBN acts as a weak agonist of CB1 receptors, but has a higher affinity to CB2 receptors, with lower affinities in comparison to THC.[7][8]
Chemistry[edit]
In contrast to THC, CBN has no double bond isomers nor stereoisomers.
Legal status[edit]
CBN is not scheduled by the United Nations' Convention on Psychotropic Substances.
United States[edit]
CBN is not scheduled at the federal level in the United States,[9] but it could legally be considered an analog of THC and sales or possession could be prosecuted under the Federal Analogue Act.
See also[edit]
References[edit]
- ^ David R. Lide (2012). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–90. ISBN 1-43988049-2.
- ^ Sigma-Aldrich Co., Cannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis.
- ^ Biotrend: Cannabinol (PDF: 21 kB)
- ^ Cannabinol in the ChemIDplus database.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ §1308.11 Schedule I.
External links[edit]
- Erowid Compounds found in Cannabis sativa
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