Vasicinone

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| ImageFile = Vasicinone.svg

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| PIN = (1S)-1-Hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-5(1H)-one

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|Section1={{Chembox Identifiers

| CASNo = 486-64-6

| PubChem = 442935

| SMILES = C1CN2C(=NC3=CC=CC=C3C2=O)[C@H]1O

| StdInChI = 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

| StdInChIKey = SDIVYZXRQHWCKF-VIFPVBQESA-N

| ChemSpiderID = 391238

| ChEBI = 9936

| ChEMBL = 3120244

| UNII = G6T5819NXM}}

|Section2={{Chembox Properties

| C=11 | H=10 | N=2 | O=2

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| Density = 1.5 g/cm3

| MeltingPtC = 200 to 202

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|Section3={{Chembox Hazards

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Vasicinone is a quinazoline alkaloid. It shows bronchodilator action in vitro{{cite journal|last1=Amin|first1=A. H.|last2=Mehta|first2=D. R.| title=A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees|journal=Nature|volume=184|issue=4695|year=1959|pages=1317 |issn=0028-0836| doi=10.1038/1841317a0|pmid=13793186|bibcode=1959Natur.184.1317A|doi-access=free}} but bronchoconstrictor action in vivo.{{cite journal |last1=Mehta|first1=D. R.|last2=Naravane|first2=J. S.|last3=Desai| first3=R. M.|title=Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae)|journal=The Journal of Organic Chemistry|volume=28 |issue=2|year=1963|pages=445–448| issn=0022-3263| doi=10.1021/jo01037a041}} Vasicinone was shown to have an antianaphylactic action. It has been found within Peganum harmala.{{cite journal |vauthors=Moloudizargari M, Mikaili P, Aghajanshakeri S, Asghari MH, Shayegh J |title=Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids |journal=Pharmacogn Rev |volume=7 |issue=14 |pages=199–212 |date=July 2013 |pmid=24347928 |pmc=3841998 |doi=10.4103/0973-7847.120524 |doi-access=free }}

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.{{cite journal| last=Avula | first=B. | title=Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis | journal=Die Pharmazie | volume=63 | issue=1 | year=2008 | pages=20–22 | doi=10.1691/ph.2008.7175 | pmid=18271297 | url=http://docserver.ingentaconnect.com/deliver/connect/govi/00317144/v63n1/s4.pdf?expires=1388798104&id=76777466&titleid=75007325 |display-authors=etal}} 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.{{cite journal|last1=Rajani|first1=M|last2=Soni|first2=S|last3=Anandjiwala|first3=Sheetal|last4=Patel|first4=G|title=Validation of different methods of preparation of Adhatoda vasica leaf juice by quantification of total alkaloids and vasicine|journal=Indian Journal of Pharmaceutical Sciences|volume=70|issue=1|year=2008|pages=36–42|issn=0250-474X|doi=10.4103/0250-474X.40329|pmc=2852058|pmid=20390078|doi-access=free}} Vasicine is reported to have a uterine stimulant effect.

References