Vasicine

Vasicine
Names
	IUPAC name 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
	Other names Peganine
Identifiers
CAS Number	6159-56-4 ;
3D model (JSmol)	Interactive image;
PubChem CID	72610;
UNII	0VFV53RMC2 ;
	SMILES C1CN2CC3=CC=CC=C3N=C2C1O;
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]

Bromhexine, a synthetic compound imitating the molecular shape of vasicine, is a common ingredient of cough medicine for its mucolytic properties; it increases the production of serous mucus in the respiratory tract which makes the phlegm thinner and less viscous, which allows the cilia to more easily transport the phlegm out of the lungs.

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.
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.
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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[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.

[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.

[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.