Vasicinone

Vasicinone
Names
	IUPAC name (3S)-3-Hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
Identifiers
CAS Number	486-64-6;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9936;
ChEMBL	ChEMBL3120244;
ChemSpider	391238;
ECHA InfoCard	100.208.620
PubChem CID	442935;
UNII	G6T5819NXM;
CompTox Dashboard (EPA)	DTXSID80964090 ;
	InChI InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1 Key: SDIVYZXRQHWCKF-VIFPVBQESA-N;
	SMILES C1CN2C(=NC3=CC=CC=C3C2=O)[C@H]1O;
Properties
Chemical formula	C11H10N2O2
Molar mass	202.213 g·mol−1
Density	1.5 g/cm3
Melting point	200 to 202 °C (392 to 396 °F; 473 to 475 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Vasicinone is a quinazoline alkaloid. It shows bronchodilatory activity in vitro[1] but bronchoconstrictory activity in vivo.[2] Vasicinone was shown to have an antianaphylactic action.[3] It has been found within Peganum harmala.[4]

Vasicinone has also been studied in combination with the related alkaloid vasicine. Both the alkaloids in combination (1:1) showed pronounced bronchodilatory activity in vivo and in vitro.[5] Both alkaloids are also respiratory stimulants.[5] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids.[5][3] Vasicine is reported to have a uterine stimulant effect.[3]

References

Amin, A. H.; Mehta, D. R. (1959). "A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees". Nature. 184 (4695): 1317–1317. doi:10.1038/1841317a0. ISSN 0028-0836.
Mehta, D. R.; Naravane, J. S.; Desai, R. M. (1963). "Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae)". The Journal of Organic Chemistry. 28 (2): 445–448. doi:10.1021/jo01037a041. ISSN 0022-3263.
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. doi:10.4103/0250-474X.40329. ISSN 0250-474X. PMC 2852058. PMID 20390078.
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.
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.

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[AminMehta1959-1] Amin, A. H.; Mehta, D. R. (1959). "A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees". Nature. 184 (4695): 1317–1317. doi:10.1038/1841317a0. ISSN 0028-0836.

[MehtaNaravane1963-2] Mehta, D. R.; Naravane, J. S.; Desai, R. M. (1963). "Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae)". The Journal of Organic Chemistry. 28 (2): 445–448. doi:10.1021/jo01037a041. ISSN 0022-3263.

[RajaniSoni2008-3] 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. doi:10.4103/0250-474X.40329. ISSN 0250-474X. PMC 2852058. PMID 20390078.

[4] 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.

[avula2008-5] 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.