Norcocaine is a minor metabolite of cocaine. It is the only confirmed pharmacologically active metabolite of cocaine,[1] 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,[2][3] 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.[4][5]
The legal status of norcocaine is somewhat ambiguous. The US DEA does not list norcocaine as a controlled substance.[6] However, some suppliers of norcocaine, like Sigma-Aldrich, consider the drug to be a Schedule II drug (same as cocaine) for the purpose of their own sales.[7][8]
Toxicityedit
The LD50 of norcocaine has been studied in mice. When administered by the intraperitoneal route, the LD50 in mice was 40 mg/kg.[9]
Controversyedit
Some researchers have suggested that hair drug testing for cocaine use should include testing for metabolites like norcocaine.[10] 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,[11][12] while others state, the residual contamination may result in a false positive test.[10][13][14][15] 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.[10] 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.[16]
Referencesedit
^. Archived from the original on 2007-09-01. Retrieved 2008-01-14.
^Wang Q, Simpao A, Sun L, Falk JL, Lau CE (January 2001). "Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics". Psychopharmacology. 153 (3): 341–52. doi:10.1007/s002130000568. PMID 11271407. S2CID 10708670.
^Just WW, Hoyer J (January 1977). "The local anesthetic potency of norcocaine, a metabolite of cocaine". Experientia. 33 (1). Birkhäuser: 70–1. doi:10.1007/BF01936761. PMID 836425. S2CID 32483810.
^Stenberg VI, Narain NK, Singh SP, Parmar SS (April 1976). "An improved synthesis of norcocaine". Journal of Heterocyclic Chemistry. 13 (2): 363–364. doi:10.1002/jhet.5570130231.
^Lazer ES, Aggarwal ND, Hite GJ, Nieforth KA, Kelleher RT, Spealman RD, et al. (December 1978). "Synthesis and biological activity of cocaine analogs I: N-alkylated norcocaine derivatives". Journal of Pharmaceutical Sciences. 67 (12): 1656–8. doi:10.1002/jps.2600671204. PMID 102759.
^(PDF). dea.gov. United States Drug Enforcement Administration, United States Department of Justice. 9 September 2014. Archived from the original (PDF) on 17 April 2016. Retrieved 8 December 2014.
^B.S, Amanda Stevens (2022-06-05). "Symptoms & Risks Of Cocaine Use & Abuse". Retrieved 2023-04-15.
^"Norcocaine". sigmaaldrich.com. Sigma-Aldrich Co. LLC. Retrieved 8 December 2014.
^Evans MA, Morarity T (January 1980). "Analysis of cocaine and cocaine metabolites by high pressure liquid chromatography". Journal of Analytical Toxicology. 4 (1): 19–22. doi:10.1093/jat/4.1.19. PMID 6927046.
^ abcCone EJ, Yousefnejad D, Darwin WD, Maguire T (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. 15 (5): 250–5. doi:10.1093/jat/15.5.250. PMID 1960975.
^Koren G, Klein J, Forman R, Graham K (July 1992). "Hair analysis of cocaine: differentiation between systemic exposure and external contamination". Journal of Clinical Pharmacology. 32 (7): 671–5. doi:10.1002/j.1552-4604.1992.tb05780.x. PMID 1640006. S2CID 39938511.
^Baumgartner WA, Hill VA (1992). "Hair analysis for drugs of abuse: Decontamination issues". Recent Developments in Therapeutic Drug Monitoring and Clinical Toxicology.
^Henderson GL, Harkey MR, Jones RT, Zhou C (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.
^Welch MJ, Sniegoski LT, Allgood CC, Habram M (1993). "Hair analysis for drugs of abuse: evaluation of analytical methods, environmental issues, and development of reference materials". Journal of Analytical Toxicology. 17 (7): 389–98. doi:10.1093/jat/17.7.389. PMID 8309210.
^Blank DL, Kidwell DA (December 1993). "External contamination of hair by cocaine: an issue in forensic interpretation". Forensic Science International. 63 (1–3): 145–56, discussion 157–60. doi:10.1016/0379-0738(93)90268-f. PMID 8138216.
^Janzen K (1992). "Concerning norcocaine, ethylbenzoylecgonine, and the identification of cocaine use in human hair". Journal of Analytical Toxicology. 16 (6): 402. doi:10.1093/jat/16.6.402. PMID 1293409.
January 01, 1970
norcocaine, confused, with, nocaine, minor, metabolite, cocaine, only, confirmed, pharmacologically, active, metabolite, cocaine, although, salicylmethylecgonine, also, speculated, active, metabolite, local, anesthetic, potential, norcocaine, been, shown, high. Not to be confused with Nocaine Norcocaine is a minor metabolite of cocaine It is the only confirmed pharmacologically active metabolite of cocaine 1 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 2 3 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 4 5 NorcocaineClinical dataAddictionliabilityHighATC codenoneLegal statusLegal statusUS Schedule IIIdentifiersIUPAC name methyl 1R 2R 3S 5S 3 benzoyloxy 8 azabicyclo 3 2 1 octane 2 carboxylateCAS Number18717 72 1 YPubChem CID644007ChemSpider559083 YUNII3SL7BR2M1ECompTox Dashboard EPA DTXSID80912319ECHA InfoCard100 161 803Chemical and physical dataFormulaC 16H 19N O 4Molar mass289 331 g mol 13D model JSmol Interactive imageSMILES COC O C H 1 C H 2CC C H N2 C C H 1OC O C3 CC CC C3InChI InChI 1S C16H19NO4 c1 20 16 19 14 12 8 7 11 17 12 9 13 14 21 15 18 10 5 3 2 4 6 10 h2 6 11 14 17H 7 9H2 1H3 t11 12 13 14 m0 s1 YKey AYDBLCSLKNTEJL RFQIPJPRSA N Y verify Contents 1 Legal status 2 Toxicity 3 Controversy 4 ReferencesLegal status editThe legal status of norcocaine is somewhat ambiguous The US DEA does not list norcocaine as a controlled substance 6 However some suppliers of norcocaine like Sigma Aldrich consider the drug to be a Schedule II drug same as cocaine for the purpose of their own sales 7 8 Toxicity editThe LD50 of norcocaine has been studied in mice When administered by the intraperitoneal route the LD50 in mice was 40 mg kg 9 Controversy editSome researchers have suggested that hair drug testing for cocaine use should include testing for metabolites like norcocaine 10 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 11 12 while others state the residual contamination may result in a false positive test 10 13 14 15 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 10 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 16 References edit Virtual Mass Spectrometry Laboratory Cocaine in Hair Archived from the original on 2007 09 01 Retrieved 2008 01 14 Wang Q Simpao A Sun L Falk JL Lau CE January 2001 Contribution of the active metabolite norcocaine to cocaine s effects after intravenous and oral administration in rats pharmacodynamics Psychopharmacology 153 3 341 52 doi 10 1007 s002130000568 PMID 11271407 S2CID 10708670 Just WW Hoyer J January 1977 The local anesthetic potency of norcocaine a metabolite of cocaine Experientia 33 1 Birkhauser 70 1 doi 10 1007 BF01936761 PMID 836425 S2CID 32483810 Stenberg VI Narain NK Singh SP Parmar SS April 1976 An improved synthesis of norcocaine Journal of Heterocyclic Chemistry 13 2 363 364 doi 10 1002 jhet 5570130231 Lazer ES Aggarwal ND Hite GJ Nieforth KA Kelleher RT Spealman RD et al December 1978 Synthesis and biological activity of cocaine analogs I N alkylated norcocaine derivatives Journal of Pharmaceutical Sciences 67 12 1656 8 doi 10 1002 jps 2600671204 PMID 102759 Controlled Substances PDF dea gov United States Drug Enforcement Administration United States Department of Justice 9 September 2014 Archived from the original PDF on 17 April 2016 Retrieved 8 December 2014 B S Amanda Stevens 2022 06 05 Symptoms amp Risks Of Cocaine Use amp Abuse Retrieved 2023 04 15 Norcocaine sigmaaldrich com Sigma Aldrich Co LLC Retrieved 8 December 2014 Evans MA Morarity T January 1980 Analysis of cocaine and cocaine metabolites by high pressure liquid chromatography Journal of Analytical Toxicology 4 1 19 22 doi 10 1093 jat 4 1 19 PMID 6927046 a b c Cone EJ Yousefnejad D Darwin WD Maguire T 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 15 5 250 5 doi 10 1093 jat 15 5 250 PMID 1960975 Koren G Klein J Forman R Graham K July 1992 Hair analysis of cocaine differentiation between systemic exposure and external contamination Journal of Clinical Pharmacology 32 7 671 5 doi 10 1002 j 1552 4604 1992 tb05780 x PMID 1640006 S2CID 39938511 Baumgartner WA Hill VA 1992 Hair analysis for drugs of abuse Decontamination issues Recent Developments in Therapeutic Drug Monitoring and Clinical Toxicology Henderson GL Harkey MR Jones RT Zhou C 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 Welch MJ Sniegoski LT Allgood CC Habram M 1993 Hair analysis for drugs of abuse evaluation of analytical methods environmental issues and development of reference materials Journal of Analytical Toxicology 17 7 389 98 doi 10 1093 jat 17 7 389 PMID 8309210 Blank DL Kidwell DA December 1993 External contamination of hair by cocaine an issue in forensic interpretation Forensic Science International 63 1 3 145 56 discussion 157 60 doi 10 1016 0379 0738 93 90268 f PMID 8138216 Janzen K 1992 Concerning norcocaine ethylbenzoylecgonine and the identification of cocaine use in human hair Journal of Analytical Toxicology 16 6 402 doi 10 1093 jat 16 6 402 PMID 1293409 Retrieved from https en wikipedia org w index php title Norcocaine amp oldid 1221373041, wikipedia, wiki, book, books, library,
