Tetrahydrocannabinol

Tetrahydrocannabinol
Clinical data
Tred names	Marinol
Leecence data	US FDA: Dronabinol;
Pregnancy; category	US: C (Risk nae ruled oot) ; ;
Dependence; liability	8–10% (Relatively low risk of tolerance)
Routes o; admeenistration	Orally, local/topical, transdermal, sublingual, inhaled
ATC code	A04AD10 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled) ; CA: Schedule II ; DE: Anlage I (Controlled) ; UK: Cless B ; US: Schedule I an Schedule III as Marinol/dronabinol ;
Pharmacokinetic data
Bioavailability	10–35% (inhalation), 6–20% (oral)
Protein bindin	97–99%
Metabolism	Maistly hepatic by CYP2C
Biological hauf-life	1.6–59 h, 25–36 h (orally administered dronabinol)
Excretion	65–80% (feces), 20–35% (urine) as acid metabolites
Identifiers
	IUPAC name (−)-(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol;
Synonyms	Dronabinol
CAS Nummer	1972-08-3 ;
PubChem CID	16078;
IUPHAR/BPS	2424;
DrugBank	DB00470 ;
ChemSpider	15266 ;
UNII	7J8897W37S;
ChEBI	CHEBI:66964 ;
ChEMBL	CHEMBL465 ;
ECHA InfoCard	100.153.676
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g/mol
3D model (Jmol)	Interactive eemage;
Specific rotation	-152° (ethanol)
Bylin pynt	157 °C (315 °F)
Solubility in watter	0.0028, (23 °C) mg/mL (20 °C)
	SMILES CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C=C(CC3)C)(C)C)O;
	InChI InChI=1S/C21H30O2/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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 ; Key:CYQFCXCEBYINGO-IAGOWNOFSA-N ;
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Tetrahydrocannabinol (THC), or mair precisely its main isomer (−)-trans-Δ⁹-tetrahydrocannabinol ( (6aR,10aR)-delta-9-tetrahydrocannabinol), is the principal psychoactive constituent (or cannabinoid) o cannabis.

References

↑ Marlowe, Douglas B. (December 2010). "The Facts On Marijuana". NADCP. Based upon several nationwide epidemiological studies, marijuana’s dependence liability has been reliably determined to be 8 to 10 percent. Cite journal requires |journal= (help)
↑ "Archived copy" (PDF). Archived frae the original (PDF) on 13 Mey 2014. Retrieved 9 November 2015.CS1 maint: archived copy as title (link)
↑ ^a ^b ^c ^d ^e Grotenhermen, F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clin Pharmacokinet. 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. Unknown parameter |subscription= ignored (help)
↑ The Royal Pharmaceutical Society of Great Britain (30 November 2006). "Cannabis". In Sean C. Sweetman (ed.). Martindale: The Complete Drug Reference: Single User (35th ed.). Pharmaceutical Press. ISBN 978-0-85369-703-9.^{[page needit]}
↑ "Tetrahydrocannabinol – Compound Summary". National Center for Biotechnology Information. PubChem. Retrieved 12 Januar 2014. Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility. The plasma protein binding of dronabinol and its metabolites is approximately 97%.
↑ Garrett ER, Hunt CA (Julie 1974). "Physicochemical properties, solubility, and protein binding of Δ⁹-tetrahydrocannabinol". J. Pharm. Sci. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640.
↑ McPartland JM, Russo EB (2001). "Cannabis and cannabis extracts: greater than the sum of their parts?" (PDF). Journal of Cannabis Therapeutics. 1 (3/4): 103–132. doi:10.1300/J175v01n03_08. Archived frae the original (PDF) on 22 Juin 2017. Retrieved 9 November 2015.

[1] Marlowe, Douglas B. (December 2010). "The Facts On Marijuana". NADCP. Based upon several nationwide epidemiological studies, marijuana’s dependence liability has been reliably determined to be 8 to 10 percent. Cite journal requires |journal= (help)

[2] "Archived copy" (PDF). Archived frae the original (PDF) on 13 Mey 2014. Retrieved 9 November 2015.CS1 maint: archived copy as title (link)

[pmid12648025-3] Grotenhermen, F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clin Pharmacokinet. 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. Unknown parameter |subscription= ignored (help)

[Martindale-4] The Royal Pharmaceutical Society of Great Britain (30 November 2006). "Cannabis". In Sean C. Sweetman (ed.). Martindale: The Complete Drug Reference: Single User (35th ed.). Pharmaceutical Press. ISBN 978-0-85369-703-9.^{[page needit]}

[5] "Tetrahydrocannabinol – Compound Summary". National Center for Biotechnology Information. PubChem. Retrieved 12 Januar 2014. Dronabinol has a large apparent volume of distribution, approximately 10 L/kg, because of its lipid solubility. The plasma protein binding of dronabinol and its metabolites is approximately 97%.

[Garrett1974-6] Garrett ER, Hunt CA (Julie 1974). "Physicochemical properties, solubility, and protein binding of Δ⁹-tetrahydrocannabinol". J. Pharm. Sci. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640.

[7] McPartland JM, Russo EB (2001). "Cannabis and cannabis extracts: greater than the sum of their parts?" (PDF). Journal of Cannabis Therapeutics. 1 (3/4): 103–132. doi:10.1300/J175v01n03_08. Archived frae the original (PDF) on 22 Juin 2017. Retrieved 9 November 2015.

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