Canabidivarina

Canabidivarina
Alerta sobre risco à saúde
Nome IUPAC 2-((1S,6S)-3-methyl-6-(prop-1-en-2-yl)
cyclohex-2-enyl)-5-propylbenzene-1,3-diol
Identificadores
Número CAS 24274-48-4
PubChem 11601669
ChemSpider 21106275
KEGG C20217
SMILES
Propriedades
Fórmula química C19H26O2
Massa molar 286.4 g mol-1
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Canabidivarina (CBDV, GWP42006) é um canabinoide não-psicoativo encontrado na Cannabis. É um homólogo do canabidiol (CBD), com a cadeia lateral substituída por duas pontes de metileno (CH2).

Embora a canabidivarina (CBDV) seja considerada uma constituinte menor dos canabinoides presentes na Cannabis, níveis elevados de CBDV foram encontrados em cepas de C. indica (C. sativa ssp. indica var. kafiristanica) do noroeste da Índia e em amostras de haxixe do Nepal.[1][2][3][4]

A CBDV é objeto de pesquisa científica por potenciais efeitos anticonvulsivantes e analgésicos.[5] Foi identificada pela primeira vez em 1969 por Vollner et al.[6]

Da mesma forma que o CBD, possui sete isômeros de ligações duplas e 30 estereoisômeros. A canabividarina está sendo desenvolvida ativamente pela farmacêutica australiana GW Pharmaceuticals (sob o codinome GWP42006),[7] principalmente por conta de uma via neuroquímica na qual atua como antiepiléptico e anticonvulsivante, propriedades já observadas anteriormente.[8] A GW iniciou um estudo de fase 2 para epilepsia em adultos,[9] e também planeja realizar testes em crianças na Austrália.[10][11]

Ver também

Referências

  1. ↑ Turner CE, Cheng PC, Lewis GS, Russell MH, Sharma GK (1979). «Constituents of Cannabis sativa XV: Botanical and chemical profile of Indian variants». Planta Medica. 37 (3): 217–25. doi:10.1055/s-0028-1097331 
  2. ↑ Hillig KW, Mahlberg PG (2004). «A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)». American Journal of Botany. 91 (6): 966–75. PMID 21653452. doi:10.3732/ajb.91.6.966Acessível livremente 
  3. ↑ Hillig KW, Mahlberg PG (junho de 2004). «A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)». American Journal of Botany. 91 (6): 966–75. PMID 21653452. doi:10.3732/ajb.91.6.966Acessível livremente 
  4. ↑ Merkus FW (agosto de 1971). «Cannabivarin and tetrahydrocannabivarin, two new constituents of hashish». Nature. 232 (5312): 579–80. Bibcode:1971Natur.232..579M. PMID 4937510. doi:10.1038/232579a0 
  5. ↑ Hill AJ, Mercier MS, Hill TD, Glyn SE, Jones NA, Yamasaki Y, Futamura T, Duncan M, Stott CG, Stephens GJ, Williams CM, Whalley BJ (2012). «Cannabidivarin is anticonvulsant in mouse and rat». British Journal of Pharmacology. 167 (8): 1629–42. PMC 3525866Acessível livremente. PMID 22970845. doi:10.1111/j.1476-5381.2012.02207.x 
  6. ↑ Vollner, L.; Bieniek, D.; Korte, F. (1 de janeiro de 1969). «Haschisch XX11XIX. Mitteillung: F. von Spulak, U. Claussen, H.-W. Fehlhaber und F. Korte, Tetrahedron 24, 5379 (1968).: Cannabidivarin, ein neuer Haschisch-Inhaltsstoff». Tetrahedron Letters. 10 (3): 145–147. ISSN 0040-4039. PMID 5778489. doi:10.1016/S0040-4039(01)87494-3 
  7. ↑ «GW Pharmaceuticals Announces Preliminary Results of Phase 2a Study for its Pipeline Compound GWP42006». GW Pharmaceuticals. 21 de fevereiro de 2018. Consultado em 28 de maio de 2019 
  8. ↑ Amada N, Yamasaki Y, Williams CM, Whalley BJ (2013). «Cannabidivarin (CBDV) suppresses pentylenetetrazole (PTZ)-induced increases in epilepsy-related gene expression». PeerJ. 1: e214. PMC 3840466Acessível livremente. PMID 24282673. doi:10.7717/peerj.214 
  9. ↑ «GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy» (Nota de imprensa). GW Pharmaceuticals. 6 de maio de 2015. Consultado em 10 de novembro de 2015 
  10. ↑ «GW Pharma Press release». Arquivado do original em 21 de novembro de 2015 
  11. ↑ «NSW advice to practitioners on Medical Cannabis trials» (PDF). Arquivado do original (PDF) em 21 de novembro de 2015 

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