Tetrahydrocannabinol

Tetrahydrocannabinol
Datos Klinikal
Kategorya sa; pagdadalangtao	C;
Dependence; liability	8–10%
Mga ruta ng; administrasyon	orally, smoked (or vaporized)
Kodigong ATC	A04AD10 (WHO) ;
Estadong Legal
Estadong legal	AU: S8 (May kontrol) ; CA: Schedule II (CA) ; Schedule I and III (US);
Datos Parmakokinetiko
Bioavailability	10–35% (inhalation), 6–20% (oral)
Pagbuklod ng protina	95–99%
Metabolismo	mostly hepatic by CYP2C
Biyolohikal na hating-buhay	1.6–59 h, 25–36 h (orally administered dronabinol)
Ekskresyon	65–80% (feces), 20–35% (urine) as acid metabolites
Mga pangkilala
	Pangalang IUPAC (−)-(6aR,10aR)-6,6,9-trimethyl-; 3-pentyl-6a,7,8,10a-tetrahydro-; 6H-benzo[c]chromen-1-ol;
Singkahulugan	Dronabinol
Bilang ng CAS	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
Datos Kemikal at Pisikal
Pormula	C21H30O2
Bigat Molar	314.4636
Modelong 3D (Jmol)	Interaktibong larawan;
Tiyak na pihit	-152° (etanol)
Punto ng pagkulo	157 °C (315 °F)
Pagkatunaw sa tubig	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 ;
(ano ito?) (patunayan)

Ang Tetrahydrocannabinol ( /ˌtɛtrəˌhaɪdrɵkəˈnæbɪnɔːl/ tet-rə-HY-drə-kə-NAB-i-nawl or /ˌtɛtrəˌhaɪdrɵkəˈnæbɪnɒl/ 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

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	Bilang ng mga stereoisomer	Pag-iral sa kalikasan	Convention on Psychotropic Substances Schedule	Istuktura
Δ^6a,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
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
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
Δ^9,11-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	Δ^1,7-tetrahydrocannabinol	3 and 4	4	Hindi	Schedule I
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
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
Δ^6a,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

4 stereoisomer ng Δ⁹-tetrahydrocannabinol
Mga pangalan		Paglalarawan	Pag-iral sa kalikasan	Istruktura
(−)-trans-Δ⁹-tetrahydrocannabinol	(6aR,10aR)-Δ⁹-tetrahydrocannabinol	levorotary trans	Oo
(−)-cis-Δ⁹-tetrahydrocannabinol	(6aS,10aR)-Δ⁹-tetrahydrocannabinol	levorotary cis	Oo
( )-trans-Δ⁹-tetrahydrocannabinol	(6aS,10aS)-Δ⁹-tetrahydrocannabinol	dextrorotary trans	Hindi
( )-cis-Δ⁹-tetrahydrocannabinol	(6aR,10aS)-Δ⁹-tetrahydrocannabinol	dextrorotary cis	Hindi

Mga sanggunian

↑ "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. (Disyembre 2010). "The Facts On Marijuana". NADCP. {{cite journal}}: Cite journal requires |journal= (tulong)CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)
↑ ^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.{{cite journal}}: CS1 maint: date auto-translated (link)
↑ ^3.0 ^3.1 Garrett, Edward R.; C. Anthony Hunt (1974). "Physicochemical properties, solubility, and protein binding of Δ⁹ -tetrahydrocannabinol". J. Pharm. Sci. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640. {{cite journal}}: Unknown parameter |month= ignored (tulong)CS1 maint: date auto-translated (link)
↑ "Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?" (PDF). Inarkibo mula sa orihinal (PDF) noong 2017-06-22. Nakuha noong 2013-04-26.{{cite web}}: CS1 maint: date auto-translated (link)
↑ Dictionary Reference: tetrahydrocannabinol: /ˌtɛtrəˌhaɪdrəkəˈnæbəˌnɔːl/, /ʔˌnɒl/
↑ 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.{{cite journal}}: CS1 maint: date auto-translated (link)
↑ Interview with the winner of the first ECNP Lifetime Achievement Award: Raphael Mechoulam, Israel Naka-arkibo 2011-04-30 sa Wayback Machine. February 2007
↑ Geller, Tom (2007). "Cannabinoids: A Secret History". Chemical Heritage Newsmagazine. 25 (2). Inarkibo mula sa orihinal noong Hunyo 19, 2008. Nakuha noong Setyembre 29, 2013.{{cite journal}}: CS1 maint: date auto-translated (link)
↑ PMID 11316486 (PubMed)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
↑ Hoaken (2003). "Drugs of abuse and the elicitation of human aggressive behavior". Addictive Behaviors. 28: 1533–1554.{{cite journal}}: CS1 maint: date auto-translated (link)

[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. (Disyembre 2010). "The Facts On Marijuana". NADCP. {{cite journal}}: Cite journal requires |journal= (tulong)CS1 maint: date auto-translated (link) CS1 maint: multiple names: mga may-akda (link)

[pmid12648025-2] 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.{{cite journal}}: CS1 maint: date auto-translated (link)

[Garrett1974-3] 3.0 ^3.1 Garrett, Edward R.; C. Anthony Hunt (1974). "Physicochemical properties, solubility, and protein binding of Δ⁹ -tetrahydrocannabinol". J. Pharm. Sci. 63 (7): 1056–64. doi:10.1002/jps.2600630705. PMID 4853640. {{cite journal}}: Unknown parameter |month= ignored (tulong)CS1 maint: date auto-translated (link)

[4] "Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?" (PDF). Inarkibo mula sa orihinal (PDF) noong 2017-06-22. Nakuha noong 2013-04-26.{{cite web}}: CS1 maint: date auto-translated (link)

[5] Dictionary Reference: tetrahydrocannabinol: /ˌtɛtrəˌhaɪdrəkəˈnæbəˌnɔːl/, /ʔˌnɒl/

[doi10.1021/ja01062a046-6] 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.{{cite journal}}: CS1 maint: date auto-translated (link)

[7] Interview with the winner of the first ECNP Lifetime Achievement Award: Raphael Mechoulam, Israel Naka-arkibo 2011-04-30 sa Wayback Machine. February 2007

[8] Geller, Tom (2007). "Cannabinoids: A Secret History". Chemical Heritage Newsmagazine. 25 (2). Inarkibo mula sa orihinal noong Hunyo 19, 2008. Nakuha noong Setyembre 29, 2013.{{cite journal}}: CS1 maint: date auto-translated (link)

[pmid11316486-9] PMID 11316486 (PubMed)
Citation will be completed automatically in a few minutes. Jump the queue or expand by hand

[10] Hoaken (2003). "Drugs of abuse and the elicitation of human aggressive behavior". Addictive Behaviors. 28: 1533–1554.{{cite journal}}: CS1 maint: date auto-translated (link)

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