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Cannabinol information


Cannabinol
Legal status
Legal status
  • CA: Unscheduled
  • UK: Class B
  • US: Unscheduled
Identifiers
IUPAC name
  • 6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol
CAS Number
  • 521-35-7 ☒N
PubChem CID
  • 2543
IUPHAR/BPS
  • 740
ChemSpider
  • 2447 checkY
UNII
  • 7UYP6MC9GH
KEGG
  • C07580 checkY
ChEMBL
  • ChEMBL74415 checkY
CompTox Dashboard (EPA)
  • DTXSID3048996 Edit this at Wikidata
ECHA InfoCard100.216.772 Edit this at Wikidata
Chemical and physical data
FormulaC21H26O2
Molar mass310.437 g·mol−1
3D model (JSmol)
  • Interactive image
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)
SMILES
  • Oc2cc(cc1OC(c3c(c12)cc(cc3)C)(C)C)CCCCC
InChI
  • 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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Cannabinol

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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...

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Cannabinoid

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cannabinoids include tetrahydrocannabinol (THC), cannabidiol (CBD) and cannabinol (CBN). Tetrahydrocannabinol (THC) is the primary psychoactive component...

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Hexahydrocannabinol

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has been found as a degradation byproduct of THC in a similar way that Cannabinol and Delta-8-THC can be formed by the Cannabis plant from Delta-9-THC degradation...

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Cannabichromene

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tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others. CBC and cannabinols are present in cannabis. It is not scheduled by the...

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Cannabivarin

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of CBV are found in the hemp plant Cannabis sativa. It is an analog of cannabinol (CBN) with the side chain shortened by two methylene bridges (-CH2-)....

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Tetrahydrocannabinol

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2-Arachidonoylglycerol, endogenous cannabinoid agonists Cannabidiol (CBD) Cannabinol (CBN), a metabolite of THC Cis-THC, an isomer of THC Delta-7-Tetrahydrocannabinol...

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Cannabicyclol

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non-psychoactive cannabinoid found in Cannabis. CBL is a degradative product like cannabinol, with cannabichromene degrading into CBL through natural irradiation or...

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Cannabinodiol

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occur as a product of the photochemical conversion of cannabinol (CBN). Cannabidiol Cannabinol Cannabichromene Cannabimovone Delta-6-CBD Dimethylheptylpyran...

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Cannabis sativa

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Synthetic THC, called dronabinol, does not contain cannabidiol (CBD), cannabinol (CBN), or other cannabinoids, which is one reason why its pharmacological...

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Cannabis use and trauma

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Cannabis use and trauma is the contribution that trauma plays in promoting the use and potential abuse of cannabis. Conversely, cannabis use has been associated...

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Cannabis edible

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Cannabidiol and Cannabinol". Pharmacokinetics and metabolism of the plant cannabinoids, delta9-tetrahydrocannabinol, cannabidiol and cannabinol. Handbook of...

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Super Lemon Haze

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lower levels of other minor cannabinoids, with approximately 1-2% of cannabinol (CBN), which can be traced to its Super Silver Haze lineage, and less...

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Cannabis tea

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instead, contain the non-psychoactive cannabinoids cannabidiol (CBD) or cannabinol (CBN)—both of which tend to go undetected in cannabis use/intoxication...

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Paracetamol

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AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide Arvanil AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin...

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Hashish

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Israel in 2005 contained all appreciable amounts of cannabidiol (CBD), and cannabinol (CBN), in addition to tetrahydrocannabinol (THC). In some samples the...

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Thyme

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(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol (cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047...

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Hash oil

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were termed cannabin (1845), cannabindon, cannabinine, crude cannabinol and cannabinol. So-called "butane honey oil" was available briefly in the 1970s...

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Onion

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(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol (cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047...

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Robert Sidney Cahn

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Ingold and Vladimir Prelog. Cahn was the first to report the structure of Cannabinol (CBN) found in Cannabis in the early 1930s. Cahn was born in Hampstead...

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Camphor

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(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol (cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047...

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