Vasicinone is a quinazoline alkaloid. It shows bronchodilator action in vitro[1] but bronchoconstrictor action in vivo.[2] Vasicinone was shown to have an antianaphylactic action.[3] It has been found within Peganum harmala.[4]
| |
| Names | |
|---|---|
| Preferred IUPAC name
(1S)-1-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-5(1H)-one | |
| Identifiers | |
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.208.620 |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C11H10N2O2 | |
| Molar mass | 202.213 g·mol−1 |
| Density | 1.5 g/cm3 |
| Melting point | 200 to 202 °C (392 to 396 °F; 473 to 475 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Vasicinone has also been studied in combination with the related alkaloid vasicine. Both the alkaloids in combination (1:1) showed pronounced bronchodilatory activity in vivo and in vitro.[5] Both alkaloids are also respiratory stimulants.[5] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids.[5][3] Vasicine is reported to have a uterine stimulant effect.[3]
References
edit- ^ Amin, A. H.; Mehta, D. R. (1959). "A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees". Nature. 184 (4695): 1317. Bibcode:1959Natur.184.1317A. doi:10.1038/1841317a0. ISSN 0028-0836. PMID 13793186.
- ^ Mehta, D. R.; Naravane, J. S.; Desai, R. M. (1963). "Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae)". The Journal of Organic Chemistry. 28 (2): 445–448. doi:10.1021/jo01037a041. ISSN 0022-3263.445-448&rft.date=1963&rft_id=info:doi/10.1021/jo01037a041&rft.issn=0022-3263&rft.aulast=Mehta&rft.aufirst=D. R.&rft.au=Naravane, J. S.&rft.au=Desai, R. M.&rfr_id=info:sid/en.wikipedia.org:Vasicinone" class="Z3988">
- ^ a b c Rajani, M; Soni, S; Anandjiwala, Sheetal; Patel, G (2008). "Validation of different methods of preparation of Adhatoda vasica leaf juice by quantification of total alkaloids and vasicine". Indian Journal of Pharmaceutical Sciences. 70 (1): 36–42. doi:10.4103/0250-474X.40329. ISSN 0250-474X. PMC 2852058. PMID 20390078.36-42&rft.date=2008&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2852058#id-name=PMC&rft.issn=0250-474X&rft_id=info:pmid/20390078&rft_id=info:doi/10.4103/0250-474X.40329&rft.aulast=Rajani&rft.aufirst=M&rft.au=Soni, S&rft.au=Anandjiwala, Sheetal&rft.au=Patel, G&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2852058&rfr_id=info:sid/en.wikipedia.org:Vasicinone" class="Z3988">
- ^ Moloudizargari M, Mikaili P, Aghajanshakeri S, Asghari MH, Shayegh J (July 2013). "Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids". Pharmacogn Rev. 7 (14): 199–212. doi:10.4103/0973-7847.120524. PMC 3841998. PMID 24347928.199-212&rft.date=2013-07&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3841998#id-name=PMC&rft_id=info:pmid/24347928&rft_id=info:doi/10.4103/0973-7847.120524&rft.aulast=Moloudizargari&rft.aufirst=M&rft.au=Mikaili, P&rft.au=Aghajanshakeri, S&rft.au=Asghari, MH&rft.au=Shayegh, J&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3841998&rfr_id=info:sid/en.wikipedia.org:Vasicinone" class="Z3988">
- ^ a b c Avula, B.; et al. (2008). "Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis" (PDF). Die Pharmazie. 63 (1): 20–22. doi:10.1691/ph.2008.7175. PMID 18271297.20-22&rft.date=2008&rft_id=info:doi/10.1691/ph.2008.7175&rft_id=info:pmid/18271297&rft.aulast=Avula&rft.aufirst=B.&rft_id=http://docserver.ingentaconnect.com/deliver/connect/govi/00317144/v63n1/s4.pdf?expires=1388798104&id=76777466&titleid=75007325&rfr_id=info:sid/en.wikipedia.org:Vasicinone" class="Z3988">