Vasicine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598146

CAS#: 6159-55-3

Description: Vasicine is an alkaloid.


Price and Availability

Size
Price

10mg
USD 500
Size
Price

Size
Price

Vasicine purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 598146
Name: Vasicine
CAS#: 6159-55-3
Chemical Formula: C11H12N2O
Exact Mass: 188.095
Molecular Weight: 188.23
Elemental Analysis: C, 70.19; H, 6.43; N, 14.88; O, 8.50


Synonym: Vasicine; l-Vasacine; l-Peganine; Peganin; (-)-Linarine;

IUPAC/Chemical Name: (R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol

InChi Key: YIICVSCAKJMMDJ-SNVBAGLBSA-N

InChi Code: InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m1/s1

SMILES Code: O[C@@H]1CCN2C1=NC3=C(C=CC=C3)C2


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Duraipandiyan V, Al-Dhabi NA, Balachandran C, Ignacimuthu S, Sankar C, Balakrishna K. Antimicrobial, antioxidant, and cytotoxic properties of vasicine acetate synthesized from vasicine isolated from Adhatoda vasica L. Biomed Res Int. 2015;2015:727304. doi: 10.1155/2015/727304. Epub 2015 Jan 14. PubMed PMID: 25632399; PubMed Central PMCID: PMC4303024.

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: Madhukar G, Tamboli ET, Rabea P, Ansari SH, Abdin MZ, Sayeed A. Rapid, sensitive, and validated UPLC/Q-TOF-MS method for quantitative determination of vasicine in Adhatoda vasica and its in vitro culture. Pharmacogn Mag. 2014 Jan;10(Suppl 1):S198-205. doi: 10.4103/0973-1296.127375. PubMed PMID: 24914304; PubMed Central PMCID: PMC4047591.

4: 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.

5: 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.

6: Sharma S, Kumar M, Kumar V, Kumar N. Metal-free transfer hydrogenation of nitroarenes in water with vasicine: revelation of organocatalytic facet of an abundant alkaloid. J Org Chem. 2014 Oct 3;79(19):9433-9. doi: 10.1021/jo5019415. Epub 2014 Sep 24. PubMed PMID: 25215900.

7: Rayees S, Mabalirajan U, Bhat WW, Rasool S, Rather RA, Panda L, Satti NK, Lattoo SK, Ghosh B, Singh G. Therapeutic effects of R8, a semi-synthetic analogue of Vasicine, on murine model of allergic airway inflammation via STAT6 inhibition. Int Immunopharmacol. 2015 May;26(1):246-56. doi: 10.1016/j.intimp.2015.03.035. Epub 2015 Apr 8. PubMed PMID: 25863236.

8: Chaliha AK, Gogoi D, Chetia P, Sarma D, Buragohain AK. An In Silico Approach for Identification of Potential Anti-Mycobacterial Targets of Vasicine and Related Chemical Compounds. Comb Chem High Throughput Screen. 2016;19(1):14-24. PubMed PMID: 26632438.

9: Liu W, Shi X, Yang Y, Cheng X, Liu Q, Han H, Yang B, He C, Wang Y, Jiang B, Wang Z, Wang C. Correction: In Vitro and In Vivo Metabolism and Inhibitory Activities of Vasicine, a Potent Acetylcholinesterase and Butyrylcholinesterase Inhibitor. PLoS One. 2015 Jun 5;10(6):e0129759. doi: 10.1371/journal.pone.0129759. eCollection 2015. PubMed PMID: 26046918; PubMed Central PMCID: PMC4457867.

10: Sharma S, Kumar M, Sharma S, Nayal OS, Kumar N, Singh B, Sharma U. Microwave assisted synthesis of phenanthridinones and dihydrophenanthridines by vasicine/KOtBu promoted intramolecular C-H arylation. Org Biomol Chem. 2016 Sep 28;14(36):8536-44. doi: 10.1039/c6ob01362g. Epub 2016 Aug 22. PubMed PMID: 27545507.

11: Shahwar D, Raza MA, Tariq S, Riasat M, Ajaib M. Enzyme inhibition, antioxidant and antibacterial potential of vasicine isolated from Adhatoda vasica Nees. Pak J Pharm Sci. 2012 Jul;25(3):651-6. PubMed PMID: 22713956.

12: Richers MT, Deb I, Platonova AY, Zhang C, Seidel D. Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine. Synthesis (Stuttg). 2013 Oct 6;45(13):1430-1748. PubMed PMID: 24052668; PubMed Central PMCID: PMC3774014.

13: Vyas T, Dash RP, Anandjiwala S, Nivsarkar M. Formulation and pharmacokinetic evaluation of hard gelatin capsule encapsulating lyophilized Vasa Swaras for improved stability and oral bioavailability of vasicine. Fitoterapia. 2011 Apr;82(3):446-53. doi: 10.1016/j.fitote.2010.12.005. Epub 2010 Dec 24. PubMed PMID: 21187127.

14: Ignacimuthu S, Shanmugam N. Antimycobacterial activity of two natural alkaloids, vasicine acetate and 2-acetyl benzylamine, isolated from Indian shrub Adhatoda vasica Ness. leaves. J Biosci. 2010 Dec;35(4):565-70. PubMed PMID: 21289439.

15: 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.

16: Pahwa GS, Zutshi U, Atal CK. Chronic toxicity studies with vasicine from Adhatoda vasica Nees. in rats and monkeys. Indian J Exp Biol. 1987 Jul;25(7):467-70. PubMed PMID: 3436645.

17: Atal CK, Sharma ML, Khajuria A, Kaul A, Arya RK. Thrombopoietic activity of vasicine hydrochloride. Indian J Exp Biol. 1982 Sep;20(9):704-9. PubMed PMID: 7160870.

18: 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.

19: 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.

20: Zutshi U, Rao PG, Soni A, Gupta OP, Atal CK. Absorption and distribution of vasicine a novel uterotonic. Planta Med. 1980 Dec;40(4):373-7. PubMed PMID: 7220651.