Vasicine

Vasicine
Names
IUPAC name
(3S)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Other names
Peganine; (-)-vasicine
Identifiers
3D model (JSmol)
UNII
  • O[C@@H]1C=2N(CC=3C(N2)=CC=CC3)CC1
Properties
C11H12N2O
Molar mass 188.230 g·mol−1
Melting point 210 °C (410 °F; 483 K)
Solubility in acetone, alcohol, chloroform Soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vasicine (peganine) is a quinazoline alkaloid. It is found in Justicia adhatoda, after which it is named. It is additionally found in Peganum harmala.[1]

Vasicine has been compared to theophylline both in vitro and in vivo.[2] It has also been studied in combination with the related alkaloid vasicinone. Both the alkaloids in combination (1:1) showed pronounced bronchodilatory activity in vivo and in vitro.[3] Both alkaloids are also respiratory stimulants.[3] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids.[3][4] Vasicine is reported to have a uterine stimulant effect.[4]

References

  1. ^ 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.
  2. ^ Nepali, Kunal; Sharma, Sahil; Ojha, Ritu; Dhar, Kanaya Lal (2012). "Vasicine and structurally related quinazolines". Medicinal Chemistry Research. 22 (1): 1–15. doi:10.1007/s00044-012-0002-5. ISSN 1054-2523. S2CID 253636554.
  3. ^ 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.
  4. ^ a b 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.