Cannabinol
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  | |
| None | |
| PubChem | CID 2543 |
| IUPHAR ligand | 740 |
| ChemSpider |
2447  |
| UNII |
7UYP6MC9GH |
| KEGG |
C07580 |
| ChEMBL |
CHEMBL74415 |
| Chemical data | |
| Formula | C21H26O2 |
| 310.4319 g/mol | |
|
SMILES
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| Physical data | |
| Melting point | 77 °C (171 °F) [1] |
|
insoluble in water[2] soluble in methanol[3] and ethanol[4] mg/mL (20 °C) | |
| (what is this?) (verify) | |
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] Because it is a somewhat selective CB2 receptor agonist, it is used experimentally as an immunosuppressant. Cannabinol is commonly found in edible hemp seeds, hemp oils/gel caps, hemp grains, and powdered Cannabis/hemp fiber.
Chemistry
In contrast to THC, CBN has no double bond isomers nor stereoisomers.
Legal status
CBN is not scheduled by the United Nations' Convention on Psychotropic Substances.
United States
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
- Cannabinoids
- Tetrahydrocannabinol (THC)
References
- ↑ Cannabinol in the ChemIDplus database.
- ↑ 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)
- ↑ 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
- Erowid Compounds found in Cannabis sativa
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