To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
Noscapine (also known as Narcotine or Anarcotine) is an alkaloid opioid agonist from plants of the Papaveraceae family, without significant painkilling properties. It is grouped as part of the benzylisoquinolines, of which papaverine is also included. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity (PDF file).
Additional recommended knowledge
Naturally it occurs as alpha enantiomer. It can be converted in the beta enantiomer when it is dissolved in alkaline water-ethanol solvutions. The lacton ring is unstable and it opens in basic media. The oposit reaction is presented in acidic media. The bond C1-C3' is unstable also. This is the bond connecting the two optical active carbon atoms. In water solution of sulphuric acid and heating it dissociats into Cortarnin (4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline) and Opic acid (6-formyl-2,3-dimethoxybenzoic acid). When Noscapine is reduced with Zn/HCl the bond C1-C3' saturates and the molecule dissociates into Hydrocortarin (2-hydroxycortarin) and Merconine (6,7-dimethoxyisobenzofuran-1(3H)-one).
Mechanism of action
Noscapine's antitussive effects appear to be primarily mediated by its sigma receptor agonist activity. Evidence for this mechanism is suggested by experimental evidence in rats. Pretreatment with rimcazole, a sigma specific antagonist, causes a dose-dependent reduction in antitussive activity of noscapine.
Cancer and stroke treatment
Noscapine is currently under investigation for use in the treatment of several cancers and hypoxic ischemia in stroke patients. In cancer treatment, noscapine appears to interfere with microtubule function, and thus the division of cancer cells in a way similar to the taxanes. Early studies in treatment of prostate cancer are very promising.
In stroke patients, noscapine blocks the bradykinine b-2 receptors. A 2003 study in Iran showed a dramatic decrease in mortality in patients treated with noscapine.
Studies are currently underway to assess the effectiveness of this drug in cancer and stroke treatment. Noscapine is non-addictive, widely available, has a low side-effect incidence, and is easily administered orally, thus it has great potential for use, especially in developing countries.
Noscapine (Nospen) has a history of Over-the-counter drug abuse in a several countries being readily available from local pharmacies as a prescription drug. The effects, beginning around 45 to 120 mins after consumption, are similar to dextromethorphan and alcohol intoxication. Abuse of noscapine and other cough suppressants (dextromethorphan, codeine, antihistamines, and xylometazoline nasal drops) has been reported to cause chronic cough lasting over one month upon withdrawal. Unlike dextromethorphan, noscapine is not an NMDA receptor antagonist.
Noscapine in Heroin
Noscapine can survive the manufacturing processes of heroin and can be found in street heroin. This is useful for law enforcement agencies, as the amounts of contaminants can identify the source of seized drugs. In 2005 in Liege, Belgium, the average noscapine concentration was around 8%.
Noscapine has also been used to identify drug users who are taking street heroin at the same time as prescribed diamorphine. Since the diamorphine in street heroin is the same as the pharmaceutical diamorphine, examination of the contaminants is the only way to test whether street heroin has been used. Other contaminants used in urine samples alongside noscapine include papaverine and acetylcodeine. Noscapine is metabolised by the body, and is itself rarely found in urine, instead being present as the primary metabolites, cotarnine and meconine . Detection is usually by gas chromatography-mass spectrometry or Liquid Chromatography-Mass Spectrometry (LCMS) but can also use a variety of other analytical techniques.
The effects shown above are not permanent, the user may experience spasms the following day after yawning. It is possible to over dose (20+ pills) and avoid taking any other drug in combination to this medication.
WARNING: Do not take noscapine with any MAOIs (monoamine oxidase inhibitors), unknown and potentially fatal effects may occur. There are no significant contraindications listed for this drug but caution should be exercised.
Categories: Sigma agonists | Antitussives
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Noscapine". A list of authors is available in Wikipedia.|