Vasicinone

Vasicinone
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 Edit this at Wikidata
UNII
  • 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/s1
    Key: SDIVYZXRQHWCKF-VIFPVBQESA-N
  • C1CN2C(=NC3=CC=CC=C3C2=O)[C@H]1O
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 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]

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]

  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. ^ 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.
  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. ^ 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.