Vasicinone
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MedKoo CAT#: 598145

CAS#: 486-64-6

Description: Vasicinone is a quinazoline alkaloid that can be isolated from A. vasica leaves and demonstrates bronchodilatory activity. It also is reported to possess antioxidant activity in nitric oxide and ABTS radical scavenging assays.


Chemical Structure

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Vasicinone
CAS# 486-64-6

Theoretical Analysis

MedKoo Cat#: 598145
Name: Vasicinone
CAS#: 486-64-6
Chemical Formula: C11H10N2O2
Exact Mass: 202.0742
Molecular Weight: 202.21
Elemental Analysis: C, 65.34; H, 4.98; N, 13.85; O, 15.82

Price and Availability

Size Price Availability Quantity
1.0mg USD 210.0 2 Weeks
5.0mg USD 450.0 2 Weeks
10.0mg USD 730.0 2 Weeks
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Synonym: Vasicinone; (-)-Vasicinone;

IUPAC/Chemical Name: (R)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

InChi Key: SDIVYZXRQHWCKF-SECBINFHSA-N

InChi Code: 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-/m1/s1

SMILES Code: O=C1N2C([C@H](O)CC2)=NC3=C1C=CC=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 202.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Sarkar C, Bose S, Banerjee S. Evaluation of hepatoprotective activity of vasicinone in mice. Indian J Exp Biol. 2014 Jul;52(7):705-11. PubMed PMID: 25059038.

2: Subramanya MD, Pai SR, Ankad GM, Hegde HV, Roy S, Hoti SL. Simultaneous determination of vasicine and vasicinone by High-performance liquid chromatography in roots of eight Sida species. Ayu. 2016 Apr-Jun;37(2):135-139. doi: 10.4103/ayu.AYU_49_16. PubMed PMID: 29200752; PubMed Central PMCID: PMC5688836.

3: Liu W, Wang Y, He DD, Li SP, Zhu YD, Jiang B, Cheng XM, Wang Z-, Wang CH. Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L. Phytomedicine. 2015 Nov 15;22(12):1088-95. doi: 10.1016/j.phymed.2015.08.005. Epub 2015 Aug 28. PubMed PMID: 26547531.

4: Wang CH, Zeng H, Wang YH, Li C, Cheng J, Ye ZJ, He XJ. Antitumor quinazoline alkaloids from the seeds of Peganum harmala. J Asian Nat Prod Res. 2015 May;17(5):595-600. doi: 10.1080/10286020.2015.1042373. PubMed PMID: 26166311.

5: Eguchi S, Suzuki T, Okawa T, Matsushita Y, Yashima E, Okamoto Y. Synthesis of Optically Active Vasicinone Based on Intramolecular Aza-Wittig Reaction and Asymmetric Oxidation(1). J Org Chem. 1996 Oct 18;61(21):7316-7319. PubMed PMID: 11667656.

6: Das C, Poi R, Chowdhury A. HPTLC determination of vasicine and vasicinone in Adhatoda vasica. Phytochem Anal. 2005 Mar-Apr;16(2):90-2. PubMed PMID: 15881115.

7: Avula B, Begum S, Ahmed S, Choudhary MI, Khan IA. Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis. Pharmazie. 2008 Jan;63(1):20-2. PubMed PMID: 18271297.

8: Pulpati H, Biradar YS, Rajani M. High-performance thin-layer chromatography densitometric method for the quantification of harmine, harmaline, vasicine, and vasicinone in Peganum harmala. J AOAC Int. 2008 Sep-Oct;91(5):1179-85. PubMed PMID: 18980138.

9: Lamchouri F, Zemzami M, Jossang A, Abdellatif A, Israili ZH, Lyoussi B. Cytotoxicity of alkaloids isolated from Peganum harmala seeds. Pak J Pharm Sci. 2013 Jul;26(4):699-706. PubMed PMID: 23811445.

10: AMIN AH, MEHTA DR. A bronchodilator alkaloid (vasicinone) from Adhatoda vasica Nees. Nature. 1959 Oct 24;184(Suppl 17):1317. PubMed PMID: 13793186.

11: Qazi AK, Hussain A, Aga MA, Ali S, Taneja SC, Sharma PR, Saxena AK, Mondhe DM, Hamid A. Cell specific apoptosis by RLX is mediated by NFκB in human colon carcinoma HCT-116 cells. BMC Cell Biol. 2014 Oct 10;15:36. doi: 10.1186/1471-2121-15-36. PubMed PMID: 25303828; PubMed Central PMCID: PMC4195704.

12: Mhaske SB, Argade NP. Concise and efficient synthesis of bioactive natural products pegamine, deoxyvasicinone, and (-)-vasicinone. J Org Chem. 2001 Dec 28;66(26):9038-40. PubMed PMID: 11749642.

13: Kamal A, Ramana KV, Rao MV. Chemoenzymatic synthesis of pyrrolo[2,1-b]quinazolinones: lipase-catalyzed resolution of vasicinone. J Org Chem. 2001 Feb 9;66(3):997-1001. PubMed PMID: 11430123.

14: CAMBRIDGE GW, JANSEN AB, JARMAN DA. Bronchodilating action of vasicinone and related compounds. Nature. 1962 Dec 22;196:1217. PubMed PMID: 14018005.

15: Gupta OP, Sharma ML, Ghatak BJ, Atal CK. Pharmacological investigations of vasicine and vasicinone--the alkaloids of Adhatoda vasica. Indian J Med Res. 1977 Oct;66(4):680-91. PubMed PMID: 608735.

16: Singh B, Sharma RA. Anti-inflammatory and antimicrobial properties of pyrroloquinazoline alkaloids from Adhatoda vasica Nees. Phytomedicine. 2013 Mar 15;20(5):441-5. doi: 10.1016/j.phymed.2012.12.015. Epub 2013 Jan 26. PubMed PMID: 23357363.

17: Pandita K, Bhatia MS, Thappa RK, Agarwal SG, Dhar KL, Atal CK. Seasonal variation of alkaloids of Adhatoda vasica and detection of glycosides and N-Oxides of vasicine and vasicinone. Planta Med. 1983 Jun;48(2):81-2. PubMed PMID: 17404955.

18: Špulák M, Pourová J, Vopršálová M, Mikušek J, Kuneš J, Vacek J, Ghavre M, Gathergood N, Pour M. Novel bronchodilatory quinazolines and quinoxalines: synthesis and biological evaluation. Eur J Med Chem. 2014 Mar 3;74:65-72. doi: 10.1016/j.ejmech.2013.12.024. Epub 2014 Jan 2. PubMed PMID: 24445313.

19: Jha DK, Panda L, Lavanya P, Ramaiah S, Anbarasu A. Detection and confirmation of alkaloids in leaves of Justicia adhatoda and bioinformatics approach to elicit its anti-tuberculosis activity. Appl Biochem Biotechnol. 2012 Nov;168(5):980-90. doi: 10.1007/s12010-012-9834-1. Epub 2012 Aug 17. PubMed PMID: 22899014.

20: Liu W, Shi X, Yang Y, Cheng X, Liu Q, Han H, Yang B, He C, Wang Y, Jiang B, Wang Z, Wang C. In vitro and in vivo metabolism and inhibitory activities of vasicine, a potent acetylcholinesterase and butyrylcholinesterase inhibitor. PLoS One. 2015 Apr 7;10(4):e0122366. doi: 10.1371/journal.pone.0122366. eCollection 2015. Erratum in: PLoS One. 2015;10(6):e0129759. PubMed PMID: 25849329; PubMed Central PMCID: PMC4388757.