Kanabidiol

Kanabidiol
Formula kimikoa	C21H30O2
SMILES kanonikoa	2D eredua
SMILES isomerikoa	CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
MolView	3D eredua
Konposizioa	karbono
Mota	[[2-[(6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol\|2-[(6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol]] (en)
Estereoisomeroa	[[1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1R-trans)-\|1,3-Benzenediol, 2-[3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-, (1R-trans)-]] (en)
Ezaugarriak
Fusio-puntua	66 °C
Masa molekularra	314,22458 Da
Erabilera
Elkarrekintza	G protein-coupled receptor 18 (en) , G protein-coupled receptor 55 (en) , Transient receptor potential cation channel subfamily M member 8 (en) eta Transient receptor potential cation channel subfamily V member 2 (en)
Identifikatzaileak
InChlKey	QHMBSVQNZZTUGM-ZWKOTPCHSA-N
CAS zenbakia	13956-29-1
ChemSpider	559095
PubChem	644019
Gmelin	69478
ChEMBL	CHEMBL190461
EC zenbakia	689-176-3
ECHA	100.215.986
CosIng	93486
MeSH	D002185
RxNorm	2045371
KNApSAcK	C00002641
UNII	19GBJ60SN5
PDB Ligand	P0T

Kanabidiola edo CBD kalamuan dauden 113 kannabinoideetako bat da, eta kalamu barietateetan landarearen osagai nagusia da^[1].

Tetrahidrokanabinola (THC) ez bezala, kalamua ez da psikoaktiboa eta aplikazio medikoetarako irismen zabalagoa duela uste da —epilepsia^[2] eta entzefalopatia epileptikoak barne, hala nola Westen sindromea, esklerosi anizkoitza^[3], antsietate-desordenak, eskizofrenia^[4] eta goragalea—. Ondorio lasaigarria eragiten du kasu gehienetan, eta minarekin lotutako nerbio-seinaleen transmisioa inhibitzen du. Ikusi da CBDk in vitro giza bularreko minbiziaren zelulen hazkundea murrizten duela eta haien inbasibitatea murrizten duela^[5].

Berez, CBD ez da intoxikatzailea, baina THCren eragin euforikoa moderatzen duela dirudi, kalamuaren isomeroa dena eta ezaugarri lasaigarri bat gehitzen diona^[6]. Hala ere, zenbait ikerketak iradokitzen dute CBDak alerta egoera areagotu dezakeela^[7]. Jakina da organismotik THCa ezabatzeko abiadura murriztu dezakeela, beharbada gibelean THCaren metabolismoa oztopatzean. Ez dirudi datuen oinarrizko multzoak hartzaileei eragiten dienik, ez CB₁ari, ez CB₂ri^[8].

Erreferentzia

↑ Aizpurua-Olaizola, Oier; Soydaner, Umut; Öztürk, Ekin; Schibano, Daniele; Simsir, Yilmaz; Navarro, Patricia; Etxebarria, Nestor; Usobiaga, Aresatz. (2016-02-26). «Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes» Journal of Natural Products 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. ISSN 0163-3864. (Noiz kontsultatua: 2020-09-06).
↑ Jones, Nicholas A.; Glyn, Sarah E.; Akiyama, Satoshi; Hill, Thomas D.M.; Hill, Andrew J.; Weston, Samantha E.; Burnett, Matthew D.A.; Yamasaki, Yuki et al.. (2012-06). «Cannabidiol exerts anti-convulsant effects in animal models of temporal lobe and partial seizures» Seizure 21 (5): 344–352. doi:10.1016/j.seizure.2012.03.001. ISSN 1059-1311. (Noiz kontsultatua: 2020-09-06).
↑ (Ingelesez) Kozela, Ewa; Lev, Nirit; Kaushansky, Nathali; Eilam, Raya; Rimmerman, Neta; Levy, Rivka; Ben‐Nun, Avraham; Juknat, Ana et al.. (2011). «Cannabidiol inhibits pathogenic T cells, decreases spinal microglial activation and ameliorates multiple sclerosis-like disease in C57BL/6 mice» British Journal of Pharmacology 163 (7): 1507–1519. doi:10.1111/j.1476-5381.2011.01379.x. ISSN 1476-5381. PMID 21449980. PMC PMC3165959. (Noiz kontsultatua: 2020-09-06).
↑ Zuardi, A. W.; Crippa, J. a. S.; Hallak, J. E. C.; Moreira, F. A.; Guimarães, F. S.. (2006-04). «Cannabidiol, a Cannabis sativa constituent, as an antipsychotic drug» Brazilian Journal of Medical and Biological Research 39 (4): 421–429. doi:10.1590/S0100-879X2006000400001. ISSN 0100-879X. (Noiz kontsultatua: 2020-09-06).
↑ (Ingelesez) McAllister, Sean D.; Christian, Rigel T.; Horowitz, Maxx P.; Garcia, Amaia; Desprez, Pierre-Yves. (2007-11-01). «Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells» Molecular Cancer Therapeutics 6 (11): 2921–2927. doi:10.1158/1535-7163.MCT-07-0371. ISSN 1535-7163. PMID 18025276. (Noiz kontsultatua: 2020-09-06).
↑ Pickens, J. T.. (1981-04). «Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content.» British Journal of Pharmacology 72 (4): 649–656. ISSN 0007-1188. PMID 6269680. PMC 2071638. (Noiz kontsultatua: 2020-09-06).
↑ (Ingelesez) Nicholson, Anthony N.; Turner, Claire; Stone, Barbara M.; Robson, Philip J.. (2004-06). «Effect of Δ-9-Tetrahydrocannabinol and Cannabidiol on Nocturnal Sleep and Early-Morning Behavior in Young Adults» Journal of Clinical Psychopharmacology 24 (3): 305–313. doi:10.1097/01.jcp.0000125688.05091.8f. ISSN 0271-0749. (Noiz kontsultatua: 2020-09-06).
↑ Straus, Stephen E.. (2000-08-15). «Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents» Proceedings of the National Academy of Sciences of the United States of America 97 (17): 9363–9364. ISSN 0027-8424. PMID 10931962. (Noiz kontsultatua: 2020-09-06).

Kanpo estekak

Datuak: Q422917
Multimedia: Cannabidiol / Q422917

[1] Aizpurua-Olaizola, Oier; Soydaner, Umut; Öztürk, Ekin; Schibano, Daniele; Simsir, Yilmaz; Navarro, Patricia; Etxebarria, Nestor; Usobiaga, Aresatz. (2016-02-26). «Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes» Journal of Natural Products 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. ISSN 0163-3864. (Noiz kontsultatua: 2020-09-06).

[2] Jones, Nicholas A.; Glyn, Sarah E.; Akiyama, Satoshi; Hill, Thomas D.M.; Hill, Andrew J.; Weston, Samantha E.; Burnett, Matthew D.A.; Yamasaki, Yuki et al.. (2012-06). «Cannabidiol exerts anti-convulsant effects in animal models of temporal lobe and partial seizures» Seizure 21 (5): 344–352. doi:10.1016/j.seizure.2012.03.001. ISSN 1059-1311. (Noiz kontsultatua: 2020-09-06).

[3] (Ingelesez) Kozela, Ewa; Lev, Nirit; Kaushansky, Nathali; Eilam, Raya; Rimmerman, Neta; Levy, Rivka; Ben‐Nun, Avraham; Juknat, Ana et al.. (2011). «Cannabidiol inhibits pathogenic T cells, decreases spinal microglial activation and ameliorates multiple sclerosis-like disease in C57BL/6 mice» British Journal of Pharmacology 163 (7): 1507–1519. doi:10.1111/j.1476-5381.2011.01379.x. ISSN 1476-5381. PMID 21449980. PMC PMC3165959. (Noiz kontsultatua: 2020-09-06).

[4] Zuardi, A. W.; Crippa, J. a. S.; Hallak, J. E. C.; Moreira, F. A.; Guimarães, F. S.. (2006-04). «Cannabidiol, a Cannabis sativa constituent, as an antipsychotic drug» Brazilian Journal of Medical and Biological Research 39 (4): 421–429. doi:10.1590/S0100-879X2006000400001. ISSN 0100-879X. (Noiz kontsultatua: 2020-09-06).

[5] (Ingelesez) McAllister, Sean D.; Christian, Rigel T.; Horowitz, Maxx P.; Garcia, Amaia; Desprez, Pierre-Yves. (2007-11-01). «Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells» Molecular Cancer Therapeutics 6 (11): 2921–2927. doi:10.1158/1535-7163.MCT-07-0371. ISSN 1535-7163. PMID 18025276. (Noiz kontsultatua: 2020-09-06).

[6] Pickens, J. T.. (1981-04). «Sedative activity of cannabis in relation to its delta'-trans-tetrahydrocannabinol and cannabidiol content.» British Journal of Pharmacology 72 (4): 649–656. ISSN 0007-1188. PMID 6269680. PMC 2071638. (Noiz kontsultatua: 2020-09-06).

[7] (Ingelesez) Nicholson, Anthony N.; Turner, Claire; Stone, Barbara M.; Robson, Philip J.. (2004-06). «Effect of Δ-9-Tetrahydrocannabinol and Cannabidiol on Nocturnal Sleep and Early-Morning Behavior in Young Adults» Journal of Clinical Psychopharmacology 24 (3): 305–313. doi:10.1097/01.jcp.0000125688.05091.8f. ISSN 0271-0749. (Noiz kontsultatua: 2020-09-06).

[8] Straus, Stephen E.. (2000-08-15). «Immunoactive cannabinoids: Therapeutic prospects for marijuana constituents» Proceedings of the National Academy of Sciences of the United States of America 97 (17): 9363–9364. ISSN 0027-8424. PMID 10931962. (Noiz kontsultatua: 2020-09-06).

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