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VASICINE, (peganine)

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Vasicine (peganine) is a quinazoline alkaloid. It is the active compound of Justicia adhatoda, after which the chemical is named.

Vasicine has been compared to theophylline both in vitro and in vivo.[1] 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.[2] Both alkaloids are also respiratory stimulants.[2] Vasicine has a cardiac–depressant effect, while vasicinone is a weak cardiac stimulant; the effect can be normalized by combining the alkaloids.[2][3] Vasicine is reported to have a uterine stimulant effect.[3]

Vasicine

Synonym Peganine

Biological Sources It is obtained from the leaves of Adhatoda vasica (L.) Nees (Acanthaceae) (Malabar Nut, Adotodai, Paveltia); and the seeds of Peganum harmala L. (Rutaceae) (Harmel, Syrian Rue, African Rue).

Chemical Structure

1, 2, 3, 9-Tetrahydropyrrolo [2, 1-b] quinazoline-3-ol; (C11H12N2O).

Isolation It is isolated from the leaves of Adhatoda vasica* and also from the seeds of Peganum harmala** by adopting the standard methods of isolation described earlier in this chapter.

Characteristic Features

dl-Form: 1. It is obtained as needles from ethanol having mp 210°C.

  1. It sublimes on being subjected to high vacuum.
  2. It is soluble in acetone, alcohol, chloroform; and slightly soluble in water, ether and

benzene.

l-Form: 1. It is obtained as needles from ethanol with mp 212°C.

  1. Its specific rotation [α ]D14-2540(C = 2.4 in CHCl3); [α ]D14–14  62° (C = 2.4 in ethanol).

Note: In dilute HCl it is obtained as its dextrorotatory form.

Identification Tests

  1. Hydrochloride dihydrate derivative is obtained as needles having mp 208°C (dry).
  2. Hydroiodide dihydrate derivative is formed as needles with mp 195°C (dry).
  3. Methiodide derivative is obtained as needles from methanol having mp 187°C.
  4. Acetyl vasicine derivative (C11H11N2O COCH3) is formed as crystals having mp 123°C and bp0.01 230-240°C.

Uses

  1. It is mostly used as an expectorant and bronchodilator.
  2. It also shows oxytocic properties very similar to those exhibited by oxytocin and methyl ergometrine.
  3. Vasicine also shows abortifacient action which is due to the release of prostaglandins.

Biosynthesis of Vasicine Various studies in Peganum harmala have evidently revealed vasicine (peganine) to be derived from the anthranilic acid, while the remaining portion of the structure comprising of a pyrrolidine ring provided by ornithine. The probable mechanism of vasicine skeleton may be explained by virtue of the nucleophilic attack from the N-atom present in anthranilate upon the pyrrolidinium cation, ultimately followed by amide formation. However, interestingly this pathway is not being adopted in Justicia adhatoda.

Vasaka

Vasaka

http://www.himalayawellness.com/products/pharmaceuticals/vasaka.htm

Effective respiratory care

Vasaka (Malabar Nut Tree/Adhatoda zeylanica) is well known in Ayurveda for its beneficial effects in respiratory ailments, particularly as an expectorant in bronchitis. The leaves, flowers, fruits and roots are used extensively for treating cold, cough, whooping-cough, chronic bronchitis and asthma.

Vasaka grows throughout India, up to an altitude of 1,300 meters.

Active constituents:

Vasaka contains the pyrroquinazoline alkaloids, including vasicine, vasicol and vasinone along with other minor constituents. Vasicine and vasinone are the major bioactive constituents of Vasaka which have bronchodilatory and antitussive properties.

The alkaloids present in the plant show significant protection against allergen-induced bronchial obstruction.

Herb Functions:

Respiratory care: Vasaka exhibits anti-inflammatory, antitussive and bronchodilatory action which eases congestion and coughing by helping loosen and thin mucus in airways. Vasaka relieves dyspnea by dilating the airways and improves overall lung functions. The herb is an excellent supportive therapy for symptomatic relief in tuberculosis and pulmonary infections.

Indications

  • Productive cough
  • Bronchitis
  • Bronchial asthma

Contraindications:

None

Recommended dose:

One capsule, twice a day or as directed by your physician

Composition:

Each capsule contains 250mg extract of Vasaka

Note: Since Himalaya’s Pure Herbs are in capsule form, some children below 14 years may find it difficult to swallow them. For this reason, Pure Herbs are recommended for children ages 14 and above.

The information on this page is not intended to be a substitute for professional medical advice. Do not use this information to diagnose or treat your problem without consulting your doctor.

 

http://kumarncsirihbt.weebly.com/publications.html

 

 

Adhatoda Vasica (Justicia Adhatoda) – Malabar Nut, Vasa, Vasaka …

Adhatoda Vasica (Justicia Adhatoda) – Malabar Nut, Vasa, Vasaka, Adulsa

 

Presentation “Herbal drugs for health Herbal drugs for health …

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… प्रयोग – पत्तियाँ खाँसी में Several alkaloids are present in the leaves and the chief principle is a quinazoline alkaloid vasicine

 

References

  1.  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.
  2.  Avula, B.; et al. (2008). “Quantitative determination of vasicine and vasicinone in Adhatoda vasica by high performance capillary electrophoresis” (PDF). Die Pharmazie – An International Journal of Pharmaceutical Sciences 63 (1): 20–22. doi:10.1691/ph.2008.7175.
  3. ^ Jump up to:a b 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.

 

 

 

Vasicine
Vasicine (peganine).png
Names
IUPAC name

1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol
Other names

Peganine
Identifiers
6159-56-4
Jmol interactive 3D Image
PubChem 72610
Properties
C11H12N2O
Molar mass 188.23 g·mol−1
Melting point 210 °C (410 °F; 483 K)
Solubility in acetone, alcohol, chloroform Soluble

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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