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Norcocaine

Chemical compound


Summary

Chemical compound

Norcocaine is a minor metabolite of cocaine. It is the only confirmed pharmacologically active metabolite of cocaine, although salicylmethylecgonine is also speculated to be an active metabolite. The local anesthetic potential of norcocaine has been shown to be higher than that of cocaine, however cocaine continues to be more widely used. Norcocaine used for research purposes is typically synthesized from cocaine. Several methods for the synthesis have been described.

Toxicity

The LD50 of norcocaine has been studied in mice. When administered by the intraperitoneal route, the LD50 in mice was 40 mg/kg.

Controversy

Some researchers have suggested that hair drug testing for cocaine use should include testing for metabolites like norcocaine. The basis for this suggestion is the potential for external contamination of hair during testing. There is considerable debate about whether current means of washing hair samples are sufficient for removing external contamination. Some researchers state the methods are sufficient, while others state, the residual contamination may result in a false positive test. Metabolites of cocaine, like norcocaine, in addition to cocaine, should be present in samples from drug users. Authors have stated that the metabolites should be present in any samples declared positive. Issues arise because the metabolites are present in only low concentrations. If the metabolites are present, it is possible for them to be from other contamination.

References

References

  1. "Virtual Mass Spectrometry Laboratory: Cocaine in Hair".
  2. (January 2001). "Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics". Psychopharmacology.
  3. (January 1977). "The local anesthetic potency of norcocaine, a metabolite of cocaine". Birkhäuser.
  4. (April 1976). "An improved synthesis of norcocaine". Journal of Heterocyclic Chemistry.
  5. (December 1978). "Synthesis and biological activity of cocaine analogs I: N-alkylated norcocaine derivatives". Journal of Pharmaceutical Sciences.
  6. . (9 September 2014). ["Controlled Substances"](http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf). *United States Drug Enforcement Administration, United States Department of Justice*.
  7. B.S, Amanda Stevens. (2022-06-05). "Symptoms & Risks Of Cocaine Use & Abuse".
  8. "Norcocaine". Sigma-Aldrich Co. LLC.
  9. (January 1980). "Analysis of cocaine and cocaine metabolites by high pressure liquid chromatography". Journal of Analytical Toxicology.
  10. (1991). "Testing human hair for drugs of abuse. II. Identification of unique cocaine metabolites in hair of drug abusers and evaluation of decontamination procedures". Journal of Analytical Toxicology.
  11. (July 1992). "Hair analysis of cocaine: differentiation between systemic exposure and external contamination". Journal of Clinical Pharmacology.
  12. (1992). "Hair analysis for drugs of abuse: Decontamination issues.".
  13. (23 September 1991). "Effect of External Contamination on the Analysis of Hair for Cocaine". Paper Presented at the Joint Meeting of Forensic Toxicologists and the Canadian Society of Forensic Scientists, Montreal, Quebec, Canada.
  14. (1993). "Hair analysis for drugs of abuse: evaluation of analytical methods, environmental issues, and development of reference materials". Journal of Analytical Toxicology.
  15. (December 1993). "External contamination of hair by cocaine: an issue in forensic interpretation". Forensic Science International.
  16. (1992). "Concerning norcocaine, ethylbenzoylecgonine, and the identification of cocaine use in human hair". Journal of Analytical Toxicology.
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This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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