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Noscapine
Systematic (IUPAC) name
(3S)- 6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro- 4-methoxy- 6-methyl- 1,3-dioxolo (4,5-g)isoquinolin-5-yl]- 1(3H)-isobenzofuranone
Identifiers
CAS number 128-62-1
ATC code R05DA07
PubChem 4544
Chemical data
Formula C 22H23NO7  
Mol. mass 413.421
Synonyms Narcotine
Pharmacokinetic data
Bioavailability ~30%
Metabolism  ?
Half life 1.5 to 4h (mean 2.5)
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?
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Noscapine (also known as Narcotine, Nectodon, Nospen, and Anarcotine) is a benzylisoquinoline alkaloid from plants of the Papaveraceae family, without significant painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. It has also been shown to have anticancer activity. [1]

Contents

Structure analysis

Naturally it occurs as the alpha enantiomer. It can be converted into the beta enantiomer when it is dissolved in alkaline water-ethanol solutions. The lactone ring is unstable and opens in basic media. The opposite reaction is presented in acidic media. The bond C1-C3' is also unstable. This is the bond connecting the two optically active carbon atoms. In aqueous solution of sulphuric acid and heating it dissociates into Cotarnine (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 Hydrocotarnine (2-hydroxycotarnine) and Meconine (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.[2]

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.[3]

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.[4]

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.

Abuse

Noscapine has a history of over-the-counter drug abuse in several countries, being readily available from local pharmacies without a prescription. The effects, beginning around 45 to 120 mins after consumption, are similar to dextromethorphan and alcohol intoxication. Unlike dextromethorphan, noscapine is not an NMDA receptor antagonist.[5]

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 Liège, Belgium, the average noscapine concentration was around 8%.[6]

Noscapine has also been used to identify drug users who are taking street heroin at the same time as prescribed diamorphine.[7] 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 performed by gas chromatography-mass spectrometry or liquid chromatography-mass spectrometry (LCMS) but can also use a variety of other analytical techniques.

Possible side-effects

The effects shown above are not permanent.

Noscapine should not be taken with any MAOIs (monoamine oxidase inhibitors), as unknown and potentially fatal effects may occur.

Noscapine should not be taken in conjunction with warfarin. The anticoagulant effects of warfarin is drastically increased by noscapine, leading to serious and possibly fatal thinning of the blood.

References

  1. ^ "Cold med ingredient may treat prostate cancer". MSNBC. http://www.msnbc.msn.com/id/28470061/. Retrieved 2009-01-02.  
  2. ^ Kamei J (1996). "Role of opioidergic and serotonergic mechanisms in cough and antitussives". Pulmonary pharmacology 9 (5-6): 349–56. doi:10.1006/pulp.1996.0046. PMID 9232674.  
  3. ^ "Noscapine effective against prostate cancer". http://www.news-medical.net/?id=21951. Retrieved 2007-07-16.  
  4. ^ "A preliminary report on the application of noscapine in the treatment of stroke". http://www.springerlink.com/content/dlp6jd6gvrtgauk3/. Retrieved 2007-07-16.  
  5. ^ PMID 2673498
  6. ^ Denooz R, Dubois N, Charlier C (2005). "[Analysis of two year heroin seizures in the Liege area]" (in French). Revue médicale de Liège 60 (9): 724–8. PMID 16265967.  
  7. ^ Paterson S, Lintzeris N, Mitchell TB, Cordero R, Nestor L, Strang J (2005). "Validation of techniques to detect illicit heroin use in patients prescribed pharmaceutical heroin for the management of opioid dependence". Addiction 100 (12): 1832–9. doi:10.1111/j.1360-0443.2005.01225.x. PMID 16367984.  

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