Tetrahydrocannabinol

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Tumalon sa: nabigasyon, hanapin
Tetrahydrocannabinol
Pangalang sistematiko (IUPAC)
(−)-(6aR,10aR)-6,6,9-trimethyl-
3-pentyl-6a,7,8,10a-tetrahydro-
6H-benzo[c]chromen-1-ol
Mga datong pangklinika
Kategorya sa pagdadalangtao C
Katayuang legal Controlled (S8) (AU) ? (CA) Schedule I and III (US)
Dependence liability 8–10%[1]
Routes orally, smoked (or vaporized)
Pharmacokinetic data
Bioavailability 10–35% (inhalation), 6–20% (oral)[2]
Protein binding 95–99%[2]
Metabolism mostly hepatic by CYP2C[2]
Half-life 1.6–59 h,[2] 25–36 h (orally administered dronabinol)
Excretion 65–80% (feces), 20–35% (urine) as acid metabolites[2]
Mga pangkilala
Bilang sa CAS 1972-08-3 Y
Kodigo sa ATC A04AD10
PubChem CID 16078
IUPHAR ligand 2424
DrugBank DB00470
ChemSpider 15266 Y
UNII 7J8897W37S Y
ChEBI CHEBI:66964 N
ChEMBL CHEMBL465 Y
Synonyms Dronabinol
Mga datong pangkimika
Pormula C21H30O2 
Mol. mass 314.4636
SMILES eMolecules & PubChem
Physical data
Boiling point 157 °C (315 °F) [4]
Solubility in water 0.0028[3] (23 °C) mg/mL (20 °C)
Spec. rot -152° (ethanol)
 N(ano ito?)  (tiyakin)
Molekulang THC sa 3D

Ang Tetrahydrocannabinol ( /ˌtɛtrəˌhdrɵkəˈnæbɪnɔːl/ tet-rə-HY-drə-kə-NAB-i-nawl or /ˌtɛtrəˌhdrɵkəˈnæbɪnɒl/ tet-rə-HY-drə-kə-NAB-i-nol;[5] THC), o mas tumpak ay ang pangunahing isomer (−)-trans-Δ9-tetrahydrocannabinol ((6aR,10aR)-delta-9-tetrahydrocannabinol) ang pangunahing sangkap na sikoaktibo o cannabinoid ng halamang cannabis o marijuana. Ito ay unang ihiniwalay noong 1964 ng mga siyentipikong Israeli na sina Raphael Mechoulam, Yechiel Gaoni at mga kasama nito sa Hebrew University of Jerusalem.[6][7][8] Ang isang pormulasyong pharmaceutical ng (−)-trans-Δ9-tetrahydrocannabinol na kilala sa INN dronabinol ay makukuha sa pamamagitan ng pagrereseta sa Estados Unidos at Canada sa ilalim ng pangalang Marinol. Ito ay isang aromatic terpenoid na may napakababang solubilidad sa tubig ngunit mabuting solubilidad sa karamihan ng mga organikong solvent sa spesipiko ay mga lipid at alkohol.[3]

Ang mga aksiyong parmakolohikal nito ay nagreresulta mula sa parsiyal na gawaing agonista sa cannabinoid receptor CB1 (Ki=10nM[13]) na matatagpuan sa sentral na sistemang nerbiyos at CB2 receptor (Ki=24nM[14]) na pangunahing inahahayag sa mga selula ng sistemang immuno. Ang mga epektong sikoaktibo nito ay pangunahing pinamamagitan ng aktibasyon ng mga CB1G-protein coupled receptor na nagpapabawas ng konsentrasyon ng ikalawang mensaherong molekulang cAMP sa pamamagitan ng pagpigil ng adenylate cyclase.

Ang THC ay may mga epektong analhesiko at ang marijuana ay magagamit upang gamutin ang kirot sa pamamagitan ng pagbabago ng paglabas ng transmitter sa dorsal root ganglion ng spinal cord at periaqueductal gray.[9] Ang ibang mga epekto nito ay kinabibilangan ng relaksasyon, pagbabago ng mga pandamang paningin, pandinig at pang-amoy, at stimulasyon ng gana sa pagkain. Ang THC ay mga katangiang antiemetiko at maaring magbawas ng agresyon sa ilang mga indibidwal. [10]

Isomerism[baguhin | baguhin ang batayan]

Dibenzopyran at monoterpenoid numbering of tetrahydrocannabinol derivatives
7 double bond isomers at kanilang 30 stereoisomer
Pagbibilang na Dibenzopyran Pagbibilang na Monoterpenoid Bilang ng mga stereoisomer Pag-iral sa kalikasan Convention on Psychotropic Substances Schedule Istuktura
Maikling pangalan Mga Chiral center Buong pangalan Maikling pangalan Mga Chiral center
Δ6a,7-tetrahydrocannabinol 9 and 10a 8,9,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ4-tetrahydrocannabinol 1 at 3 4 Hindi Schedule I Delta6a,7-Tetrahydrocannabinol.png
Δ7-tetrahydrocannabinol 6a, 9 and 10a 6a,9,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ5-tetrahydrocannabinol 1, 3 at 4 8 Hindi Schedule I Delta7-Tetrahydrocannabinol.png
Δ8-tetrahydrocannabinol 6a and 10a 6a,7,10,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ6-tetrahydrocannabinol 3 at 4 4 Oo Schedule I Delta8-Tetrahydrocannabinol.png
Δ9,11-tetrahydrocannabinol 6a and 10a 6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9-methylene-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ1,7-tetrahydrocannabinol 3 and 4 4 Hindi Schedule I Delta9,11-Tetrahydrocannabinol.png
Δ9-tetrahydrocannabinol 6a and 10a 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ1-tetrahydrocannabinol 3 and 4 4 Oo Schedule II Delta9-Tetrahydrocannabinol.png
Δ10-tetrahydrocannabinol 6a and 9 6a,7,8,9-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ2-tetrahydrocannabinol 1 and 4 4 Hindi Schedule I Delta10-Tetrahydrocannabinol.png
Δ6a,10a-tetrahydrocannabinol 9 7,8,9,10-tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol Δ3-tetrahydrocannabinol 1 2 Hindi Schedule I Delta6a,10a-Tetrahydrocannabinol.png
4 stereoisomer ng Δ9-tetrahydrocannabinol
Mga pangalan Paglalarawan Pag-iral sa kalikasan Istruktura
(−)-trans-Δ9-tetrahydrocannabinol (6aR,10aR)-Δ9-tetrahydrocannabinol levorotary trans Oo (−)-(6aR,10aR)-Δ9-Tetrahydrocannabinol (with hydrogen atoms shown).svg
(−)-cis-Δ9-tetrahydrocannabinol (6aS,10aR)-Δ9-tetrahydrocannabinol levorotary cis Oo (−)-(6aS,10aR)-Δ9-Tetrahydrocannabinol (with hydrogen atoms shown).svg
(+)-trans-Δ9-tetrahydrocannabinol (6aS,10aS)-Δ9-tetrahydrocannabinol dextrorotary trans Hindi (+)-(6aS,10aS)-Δ9-Tetrahydrocannabinol (with hydrogen atoms shown).svg
(+)-cis-Δ9-tetrahydrocannabinol (6aR,10aS)-Δ9-tetrahydrocannabinol dextrorotary cis Hindi (+)-(6aR,10aS)-Δ9-Tetrahydrocannabinol (with hydrogen atoms shown).svg

Mga sanggunian[baguhin | baguhin ang batayan]

  1. "Based upon several nationwide epidemiological studies, marijuana’s dependence liability has been reliably determined to be 8 to 10 percent." Douglas B. Marlowe, J.D., Ph.D. (December 2010). The Facts On Marijuana. NADCP. 
  2. 2.0 2.1 2.2 2.3 2.4 Grotenhermen F (2003). "Pharmacokinetics and pharmacodynamics of cannabinoids". Clin Pharmacokinet 42 (4): 327–60. doi:10.2165/00003088-200342040-00003. PMID 12648025. 
  3. 3.0 3.1 Garrett, Edward R.; C. Anthony Hunt (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. 
  4. "Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?". http://www.cannabis-med.org/data/pdf/2001-03-04-7.pdf. Hinango noong 2013-04-26. 
  5. Dictionary Reference: tetrahydrocannabinol: /ˌtɛtrəˌhdrəkəˈnæbəˌnɔːl/, /ʔˌnɒl/
  6. Gaoni, Y.; Mechoulam, R. (1964). "Isolation, structure and partial synthesis of an active constituent of hashish". Journal of the American Chemical Society 86 (8): 1646–1647. doi:10.1021/ja01062a046. 
  7. Interview with the winner of the first ECNP Lifetime Achievement Award: Raphael Mechoulam, Israel February 2007
  8. Geller, Tom (2007). "Cannabinoids: A Secret History". Chemical Heritage Newsmagazine 25 (2). Archived from the original noong June 19, 2008. http://web.archive.org/web/20080619013348/http://chemicalheritage.org/pubs/ch-v25n2-articles/feature_cannabinoids.html. 
  9. PMID 11316486 (PubMed)
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  10. Hoaken (2003). "Drugs of abuse and the elicitation of human aggressive behavior". Addictive Behaviors 28: 1533–1554.