Vasicine

Vasicine
Names
	IUPAC name (3S)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
	Other names Peganine; (-)-vasicine
Identifiers
CAS Number	6159-55-3 ; (±): 6159-56-4;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.025.619
PubChem CID	667496;
UNII	6C2ZBI733P ;
CompTox Dashboard (EPA)	DTXSID601024261 ;
	SMILES O[C@@H]1C=2N(CC=3C(N2)=CC=CC3)CC1;
Properties
Chemical formula	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). Infobox references

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

^ 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.
^ 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.
^ ^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.
^ ^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.

[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.

[NepaliSharma2012-2] 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.

[avula2008-3] 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.

[RajaniSoni2008-4] 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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