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From Wikipedia, the free encyclopedia

Cannabinol
Cannabinol.svg
Cannabinol 3D.png
Clinical data
Routes of
administration
Oral, Inhaled
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.216.772
Chemical and physical data
Formula C21H26O2
Molar mass 310.4319 g/mol
3D model (JSmol)
Melting point 77 °C (171 °F) [4]
Solubility in water

insoluble in water[1]

soluble in methanol[2] and ethanol[3] mg/mL (20 °C)
 NYesY (what is this?)  (verify)

Cannabinol (CBN) is a non-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] Degraded or oxidized cannabis products, such as low-quality baled cannabis and traditionally produced hashish, are high in CBN, but modern production processes minimize the formation of CBN.[10][unreliable source?] Cannabinol has been shown to have analgesic properties.[11]

Cannabinol show potential immunosuppressive and anti-inflammatory activities, and preferentially binds to the cannabinoid G-protein coupled receptor CB2, which is mainly expressed on a variety of immune cells, such as T-cells, B-cells, macrophages and dendritic cells. Stimulation of CB2 receptors by cannabinol may both trigger apoptosis in these cells and inhibit the production of a variety of cytokines. Cannabinol exerts minimal affinity for CB1 and has a weak effect on the central nervous system.[12]

Unlike other cannabinoids, CBN does not stem from cannabigerol (CBG). There is no clinical evidence that THC breaks down naturally into CBN once the THC has become decarboxylated and forms delta-9 THC. CBN is formed by decarboxylation of CBNA.[13]

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Transcription

Contents

Chemistry

In contrast to THC, CBN has no double bond isomers nor stereoisomers. Both THC and CBN activate the CB1 and CB2 receptors.[14][unreliable source?] Chemically, CBN is closely related to cannabidiol (CBD).

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

United States

Cannabinol 10 mg transdermal patches
Cannabinol 10 mg transdermal patches sold at marijuana dispensaries in Colorado, USA

In the United States, federal and state laws regarding the legality of cannabis products are confusing and at times contradictory.[16] CBN is not listed in the list of scheduled controlled substances in the USA.[17] However, it is possible that CBN could legally be considered an analog of THC or CBD, both of which are Schedule I substances, and therefore sales or possession could potentially be prosecuted under the Federal Analogue Act.[18] It is also possible that CBN may not meet the legal standard of an analogue (of THC) for the purposes of bringing forth a prosecution under the Federal Analogue Act. 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.[19] this action has led to additional uncertainty about the legal status.[20]

References

  1. ^ David R. Lide (2012). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–90. ISBN 1-43988049-2. 
  2. ^ Sigma-Aldrich Co., Cannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis.
  3. ^ Biotrend: Cannabinol (PDF: 21 kB)
  4. ^ Cannabinol in the ChemIDplus database.
  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. doi:10.3389/fpls.2016.00019. ISSN 1664-462X. PMC 4740396Freely accessible. 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. 
  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. ^ "CBN: Stale THC Helps Patients Sleep". June 1, 2015. 
  11. ^ Sofia, R. Duane; Vassar, Heidi B.; Knobloch, Linda C. (1975). "Comparative analgesic activity of various naturally occurring cannabinoids in mice and rats". Psychopharmacologia. 40 (4): 285–295. doi:10.1007/BF00421466. 
  12. ^ "NIA National Cancer Institute; NCIthesaurus". Cannabinol (Code C84510). 
  13. ^ Medical Jane, Cannabinol CBN
  14. ^ CBN: The Lazy Stoner's Cannabinoid[dead link]
  15. ^ UN International Drug Control Conventions
  16. ^ Mead, Alice (2017). "The legal status of cannabis (marijuana) and cannabidiol (CBD) under U.S. Law". Epilepsy & Behavior. doi:10.1016/j.yebeh.2016.11.021. 
  17. ^ §1308.11 Schedule I.
  18. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
  19. ^ "Establishment of a New Drug Code for Marihuana Extract" (PDF). Federal Register, Vol. 81, No. 240. December 14, 2016. 
  20. ^ See, for example: "DEA Sparks New Battle With Marijuana Extract Makers". Forbes. December 19, 2016. 

External links

This page was last edited on 29 December 2017, at 15:10.
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