| 词条 | Cannabinol |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477165540 | IUPAC_name = 6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol | image = Cannabinol.svg | image2 = Cannabinol 3D.png | tradename = | pregnancy_category = | legal_CA = Schedule II | legal_UK = Class B | legal_status = | routes_of_administration = Oral, inhaled | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 521-35-7 | ATC_prefix = none | ATC_suffix = | PubChem = 2543 | IUPHAR_ligand = 740 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2447 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7UYP6MC9GH | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C07580 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 74415 | C=21 | H=26 | O=2 | molecular_weight = 310.4319 g/mol | smiles = Oc2cc(cc1OC(c3c(c12)cc(cc3)C)(C)C)CCCCC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = VBGLYOIFKLUMQG-UHFFFAOYSA-N | density = | melting_point = 77 | melting_notes = [1] | boiling_point = | boiling_notes = | solubility = insoluble in water[2] soluble in methanol[3] and ethanol[4] | specific_rotation = }} 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][10] Degraded or oxidized cannabis products, such as low-quality baled cannabis and traditionally produced hashish, are high in CBN.{{cn|date=September 2018}} Unlike other cannabinoids, CBN does not stem directly from cannabigerol (CBG) or cannabigerolic acid (CBGA), but rather is the degraded product of tetrahydrocannabinolic acid (THCA).{{cn|date=September 2018}} If cannabis is exposed to air or ultraviolet light (for example, in sunlight) for a prolonged period of time, THCA will convert to cannabinolic acid (CBNA). CBN is then formed by decarboxylation of CBNA. ChemistryIn contrast to THC, CBN has no double bond isomers nor stereoisomers. Both THC and CBN activate the CB1 and CB2 receptors.{{cn|date=March 2018}} Chemically, CBN is closely related to cannabidiol (CBD). Legal statusCBN 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,[11] so the signatory countries to these international drug control treaties are not required by these treaties to control CBN. CanadaIn Canada, CBN is a Schedule II controlled substance as defined by the Controlled Drugs and Substances Act.[12] United StatesIn the United States, federal and state laws regarding the legality of cannabis products are confusing and at times contradictory.[13] CBN is not listed in the list of scheduled controlled substances in the USA.[14] 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.[15] 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.[16] This action has led to additional uncertainty about the legal status.[17] References1. ^{{ChemID|521-35-7}}. 2. ^{{cite book |author=David R. Lide |title=CRC Handbook of Chemistry and Physics |publisher=CRC Press |year=2012 |isbn=978-1-43988049-4 |pages=3–90 |url=https://books.google.com/books?id=-BzP7Rkl7WkC&pg=PA3-90}} 3. ^{{Aldrich|cerillian|id=c046|name=Cannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis}} 4. ^Biotrend: Cannabinol (PDF: 21 kB) 5. ^{{cite journal |vauthors=Karniol IG, Shirakawa I, Takahashi RN, Knobel E, Musty RE |title=Effects of delta9-tetrahydrocannabinol and cannabinol in man |journal=Pharmacology |volume=13 |issue=6 |pages=502–12 |year=1975 |pmid=1221432 |doi=10.1159/000136944 |url= }} 6. ^{{Cite journal|last=Andre|first=Christelle M.|last2=Hausman|first2=Jean-Francois |last3=Guerriero |first3=Gea |date=2016-02-04 |title=Cannabis sativa: The Plant of the Thousand and One Molecules|journal=Frontiers in Plant Science |volume=7 |pages=19 |doi=10.3389/fpls.2016.00019 |issn=1664-462X |pmc=4740396 |pmid=26870049}} 7. ^{{cite journal |vauthors=McCallum ND, Yagen B, Levy S, Mechoulam R |title=Cannabinol: a rapidly formed metabolite of delta-1- and delta-6-tetrahydrocannabinol |journal=Experientia |volume=31 |issue=5 |pages=520–1 |date=May 1975 |pmid=1140243 |doi= 10.1007/bf01932433|url= }} 8. ^{{cite journal |vauthors=Mahadevan A, Siegel C, Martin BR, Abood ME, Beletskaya I, Razdan RK |title=Novel cannabinol probes for CB1 and CB2 cannabinoid receptors |journal=Journal of Medicinal Chemistry |volume=43 |issue=20 |pages=3778–85 |date=October 2000 |pmid=11020293 |doi=10.1021/jm0001572}} 9. ^{{cite journal |vauthors=Petitet F, Jeantaud B, Reibaud M, Imperato A, Dubroeucq MC |title=Complex pharmacology of natural cannabinoids: evidence for partial agonist activity of delta9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors |journal=Life Sciences |volume=63 |issue=1 |pages=PL1–6 |year=1998 |pmid=9667767 |doi=10.1016/S0024-3205(98)00238-0 |url=http://linkinghub.elsevier.com/retrieve/pii/S0024320598002380}} 10. ^{{Cite web|url=https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C84510|title=NIA National Cancer Institute; NCIthesaurus|last=|first=|date=|website=Cannabinol (Code C84510)|archive-url=|archive-date=|dead-url=|access-date=}} 11. ^[https://www.unodc.org/unodc/en/commissions/CND/conventions.html UN International Drug Control Conventions] 12. ^{{cite web | url = http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-13.html#h-32 | title = Controlled Drugs and Substances Act (S.C. 1996, c. 19), SCHEDULE II | publisher = Government of Canada}} 13. ^{{Cite journal | doi = 10.1016/j.yebeh.2016.11.021| pmid = 28169144| title = The legal status of cannabis (marijuana) and cannabidiol (CBD) under U.S. Law| journal = Epilepsy & Behavior| volume = 70| issue = Pt B| pages = 288–291| year = 2017| last1 = Mead| first1 = Alice}} 14. ^§1308.11 Schedule I. 15. ^[https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary] 16. ^{{Cite web | url = https://www.gpo.gov/fdsys/pkg/FR-2016-12-14/pdf/2016-29941.pdf | work = Federal Register, Vol. 81, No. 240 | title = Establishment of a New Drug Code for Marihuana Extract | date = December 14, 2016}} 17. ^See, for example: {{Cite web | url = https://www.forbes.com/sites/debraborchardt/2016/12/19/a-new-battle-is-sparked-between-dea-and-cbd-makers | title = DEA Sparks New Battle With Marijuana Extract Makers | publisher = Forbes | date = December 19, 2016}} External links{{Portal|Cannabis}}
5 : Cannabinoids|Natural phenols|Benzochromenes|CB1 receptor agonists|CB2 receptor agonists |
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