Tetrahydrocannabinol (THC), or mair precisely its main isomer (−)-trans9-tetrahydrocannabinol ((6aR,10aR)-delta-9-tetrahydrocannabinol), is the principal psychoactive constituent (or cannabinoid) o cannabis.

Tetrahydrocannabinol
Tetrahydrocannabinol.svg
Delta-9-tetrahydrocannabinol-from-tosylate-xtal-3D-balls.png
Clinical data
Tred namesMarinol
Leecence data
Pregnancy
category
  • US: C (Risk nae ruled oot)
Dependence
liability
8–10% (Relatively low risk of tolerance)[1]
Routes o
admeenistration
Orally, local/topical, transdermal, sublingual, inhaled
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability10–35% (inhalation), 6–20% (oral)[3]
Protein bindin97–99%[3][4][5]
MetabolismMaistly hepatic by CYP2C[3]
Biological hauf-life1.6–59 h,[3] 25–36 h (orally administered dronabinol)
Excretion65–80% (feces), 20–35% (urine) as acid metabolites[3]
Identifiers
SynonymsDronabinol
CAS Nummer
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard100.153.676
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g/mol
3D model (Jmol)
Specific rotation-152° (ethanol)
Bylin pynt157 °C (315 °F) [7]
Solubility in watter0.0028,[6] (23 °C) mg/mL (20 °C)
 NYesY (whit is this?)  (verify)

ReferencesEedit

  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. http://www.fda.gov/ohrms/dockets/dockets/05n0479/05N-0479-emc0004-04.pdf
  3. 3.0 3.1 3.2 3.3 3.4 Grotenhermen, F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clin Pharmacokinet. 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. (Subscription required (help)). Cite uses deprecated parameter |subscription= (help)
  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 January 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%.
  6. Garrett ER, Hunt CA (July 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.