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Vasicinone

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Vasicinone
Names
Preferred IUPAC name (1S)-1-Hydroxy-2,3-dihydropyrroloquinazolin-5(1H)-one
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.620 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1Key: SDIVYZXRQHWCKF-VIFPVBQESA-N
SMILES
  • C1CN2C(=NC3=CC=CC=C3C2=O)1O
Properties
Chemical formula C11H10N2O2
Molar mass 202.213 g·mol
Density 1.5 g/cm
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 , 100 kPa). Infobox references
Chemical compound

Vasicinone is a quinazoline alkaloid. It shows bronchodilator action in vitro but bronchoconstrictor action in vivo. Vasicinone was shown to have an antianaphylactic action. It has been found within Peganum harmala.

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. Both alkaloids are also respiratory stimulants. Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids. Vasicine is reported to have a uterine stimulant effect.

References

  1. 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.
  2. 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.
  3. ^ 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.
  4. 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.
  5. ^ 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.
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