Vasicine

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Vasicine
Vasicin.svg
Names
IUPAC name
(3S)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Other names
Peganine; (-)-vasicine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2
    Key: YIICVSCAKJMMDJ-UHFFFAOYSA-N
  • 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, chloroformSoluble
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. 1 2 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. 1 2 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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