Tetrahidrokanabinolna kiselina

Tetrahidrokanabinolna kiselina
IUPAC ime
	(6aR,10aR)-1-hidroksi-6,6,9-trimetil-3-pentil-6a,7,8,10a-tetrahidro-6h-benzo[c]hromen-2-karboksilna kiselina
Identifikatori
CAS broj	23978-85-0
ATC kod	none
PubChem	CID 98523
ChemSpider	88974
Hemijski podaci
Formula	C22H30O4
Molarna masa	358,4733 g/mol
	SMILES CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1C(=O)O)O; ;

Tetrahidrokanabinolna kiselina (THCA, 2-COOH-THC) je biosintetički precursor tetrahidrokanabinola (THC), aktivne komponente kanabisa.^[1]^[2]^[3]^[4] THCA je prisutan u varijabilnim količinama u svežem, neosušenom kanabisu, ali se progresiivno dekarboksiluje do THC tokom sušenja, a posebno tokom intezivnog zagrevanja, npr. pri pušenju kanabisa.^[5]

Reference

^ Baker PB, Taylor BJ, Gough TA (1981), „The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products”, Journal of Pharmacy and Pharmacology, 33 (6): 369—72, PMID 6115009
^ Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F (17. 9. 2004), „The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.”, Journal of Biological Chemistry, 279 (38): 39767—74, PMID 15190053
^ Moore C, Rana S, Coulter C (1. 6. 2007), „Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid”, J Chromatogr B Analyt Technol Biomed Life Sci., 852 (1-2): 459—64, PMID 17321807
^ Taura F. (2009), „Studies on tetrahydrocannabinolic acid synthase that produces the acidic precursor of tetrahydrocannabinol, the pharmacologically active cannabinoid in marijuana”, Drug Discoveries and Therapeutics, 3 (3): 83—7, PMID 22495534
^ Dussy FE, Hamberg C, Luginbühl M, Schwerzmann T, Briellmann TA (2005-04-20), „Isolation of Delta9-THCA-A from hemp and analytical aspects concerning the determination of Delta9-THC in cannabis products”, Forensic Science International, 149 (1): 3—10, PMID 15734104

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[1] Baker PB, Taylor BJ, Gough TA (1981), „The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products”, Journal of Pharmacy and Pharmacology, 33 (6): 369—72, PMID 6115009

[2] Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F (17. 9. 2004), „The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.”, Journal of Biological Chemistry, 279 (38): 39767—74, PMID 15190053

[3] Moore C, Rana S, Coulter C (1. 6. 2007), „Simultaneous identification of 2-carboxy-tetrahydrocannabinol, tetrahydrocannabinol, cannabinol and cannabidiol in oral fluid”, J Chromatogr B Analyt Technol Biomed Life Sci., 852 (1-2): 459—64, PMID 17321807

[4] Taura F. (2009), „Studies on tetrahydrocannabinolic acid synthase that produces the acidic precursor of tetrahydrocannabinol, the pharmacologically active cannabinoid in marijuana”, Drug Discoveries and Therapeutics, 3 (3): 83—7, PMID 22495534

[5] Dussy FE, Hamberg C, Luginbühl M, Schwerzmann T, Briellmann TA (2005-04-20), „Isolation of Delta9-THCA-A from hemp and analytical aspects concerning the determination of Delta9-THC in cannabis products”, Forensic Science International, 149 (1): 3—10, PMID 15734104

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