WordNet

psychoactive substance present in marijuana (同)THC
a resin obtained from the hemp plant; thought to be the active narcotic agent in marijuana (同)cannabis resin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/14 03:26:08」(JST)

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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] Cannabinol has been shown to have analgesic properties.^[9]

Unlike other cannabinoids, CBN does not stem from CBG, but is the degraded product of THC. If cannabis is exposed to air or ultraviolet light for a prolonged period of time, THCA will convert to CBNA. CBN is then formed by decarboxylation of CBNA.^[10]

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,^[11] but it could legally be considered an analog of THC and sales or possession could be prosecuted under the Federal Analogue Act.

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

References

^ 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.
^ http://link.springer.com/article/10.1007%2FBF00421466
^ Medical Jane, Cannabinol CBN
^ §1308.11 Schedule I.

External links

Erowid Compounds found in Cannabis sativa

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 合成カンナビノイド：急性中毒 synthetic cannabinoids acute intoxication
2. 小児における痙攣およびてんかん：難治性の痙攣および予後 seizures and epilepsy in children refractory seizures and prognosis

English Journal

Water-compatible imprinted pills for sensitive determination of cannabinoids in urine and oral fluid.

Cela-Pérez MC1, Bates F1, Jiménez-Morigosa C2, Lendoiro E3, de Castro A2, Cruz A2, López-Rivadulla M2, López-Vilariño JM4, González-Rodríguez MV1.
Journal of chromatography. A.J Chromatogr A.2016 Jan 15;1429:53-64. doi: 10.1016/j.chroma.2015.12.011. Epub 2015 Dec 8.
A novel molecularly imprinted solid phase extraction (MISPE) methodology followed by liquid chromatography tandem mass spectrometry (LC-MS/MS) has been developed using cylindrical shaped molecularly imprinted pills for detection of Δ(9)-tetrahydrocannabinol (THC), 11-nor-Δ(9)-tetrahydrocannabinol
PMID 26718187

Amphetamines and cannabinoids testing in hair: Evaluation of results from a two-year period.

Burgueño MJ1, Alonso A2, Sánchez S2.
Forensic science international.Forensic Sci Int.2016 Jan 11;265:47-53. doi: 10.1016/j.forsciint.2016.01.003. [Epub ahead of print]
This paper presents an overview of a set of amphetamines and cannabinoids tests performed on head hair samples from the Medico-Legal sector at the Madrid Department of the Spanish National Institute of Toxicology and Forensic Sciences during the years 2013 and 2014. The hair samples were tested for
PMID 26829334

Influence of thermal hair straightening on cannabis and cocaine content in hair.

Ettlinger J1, Yegles M2.
Forensic science international.Forensic Sci Int.2016 Jan 7;265:13-16. doi: 10.1016/j.forsciint.2016.01.002. [Epub ahead of print]
It has been shown that cosmetic treatment like bleaching and perming may lead to an important decrease of drugs of abuse content in hair. Currently, hair straightening has become a regular hair treatment especially for women. The aim of this preliminary study was to investigate the effect of in vitr
PMID 26826847

Japanese Journal

Comparison in the In Vitro Inhibitory Effects of Major Phytocannabinoids and Polycyclic Aromatic Hydrocarbons Contained in Marijuana Smoke on Cytochrome P450 2C9 Activity

Drug Metabolism and Pharmacokinetics 27(3), 294-300, 2012
NAID 130004463253

Cannabinoid Receptor 1 Binding Activity and Quantitative Analysis of Cannabis sativa L. Smoke and Vapor

Chemical and Pharmaceutical Bulletin 58(2), 201-207, 2010
NAID 130000161592

Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 852(1), 459-464, 2007-06-01
NAID 10025802597

Related Pictures

This licensing tag was added to this file File:Cannabinol-C2.png - Wikipedia, the is cannabinol cbn whaxy cannabinol Cannabinol (CBN) molecule Cannabinol - Wikipedia, the free and Derivates Cannabinol (CBN

★リンクテーブル★

リンク元	「カンナビノール」
拡張検索	「tetrahydrocannabinol」

「カンナビノール」

Cannabinol
Systematic (IUPAC) name
	6,6,9-Trimethyl-3-pentyl-benzo[c]chromen-1-ol
Identifiers
CAS Number	521-35-7
ATC code	None
PubChem	CID: 2543
IUPHAR/BPS	740
ChemSpider	2447
UNII	7UYP6MC9GH
KEGG	C07580
ChEMBL	CHEMBL74415
Chemical data
Formula	C21H26O2
Molecular mass	310.4319 g/mol
	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 ; Key:VBGLYOIFKLUMQG-UHFFFAOYSA-N ;
Physical data
Melting point	77 °C (171 °F)
Solubility in water	insoluble in water soluble in methanol and ethanol mg/mL (20 °C)
(what is this?) (verify)

　　[★]

英

cannabinol

大麻活性成分

「tetrahydrocannabinol」

　　[★] テトラヒドロカンナビノール, THC

[CRC-1] David R. Lide (2012). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–90. ISBN 1-43988049-2.

[Sigma-2] Sigma-Aldrich Co., Cannabinol solution, 1.0 mg/mL in methanol, analytical standard, for drug analysis.

[3] Biotrend: Cannabinol (PDF: 21 kB)

[ChemIDplus-4] Cannabinol in the ChemIDplus database.

[pmid1221432-5] 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.

[pmid1140243-6] 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.

[pmid11020293-7] 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.

[pmid9667767-8] 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.

[9] ttp://link.springer.com/article/10.1007%2FBF00421466

[10] Medical Jane, Cannabinol CBN

[PART_1308_.E2.80.94_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-11] §1308.11 Schedule I.

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