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Vasicine

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Vasicine
Names
IUPAC name (3S)-1,2,3,9-Tetrahydropyrroloquinazolin-3-ol
Other names Peganine; (-)-vasicine
Identifiers
CAS Number
3D model (JSmol)
PubChem CID
UNII
CompTox Dashboard (EPA)
SMILES
  • O1C=2N(CC=3C(N2)=CC=CC3)CC1
Properties
Chemical formula C11H12N2O
Molar mass 188.230 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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

Vasicine has been compared to theophylline both in vitro and in vivo. 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. 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. 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. ^ 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. ^ 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.
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