Norcocaine

Last updated
Norcocaine
Norcocaine.png
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.161.803 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H19NO4
Molar mass 289.331 g·mol−1
3D model (JSmol)
  • COC(=O)[C@@H]1[C@H]2CC[C@H](N2)C[C@@H]1OC(=O)C3=CC=CC=C3
  • 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 Yes check.svgY
  • Key:AYDBLCSLKNTEJL-RFQIPJPRSA-N Yes check.svgY
   (verify)

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]

Contents

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]

Toxicity

The LD50 of norcocaine has been studied in mice. When administered by the intraperitoneal route, the LD50 in mice was 40 mg/kg. [9]

Controversy

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]

Related Research Articles

<span class="mw-page-title-main">PCHP</span> Chemical compound

1-(1-Phenylcyclohexyl)-4-hydroxypiperidine (PCHP) is a metabolite of phencyclidine (PCP). PCHP can be detected in the hair, urine, stool, sweat, and saliva of PCP users.

<span class="mw-page-title-main">Hair analysis</span> Chemical analysis of a hair sample

Hair analysis may refer to the chemical analysis of a hair sample, but can also refer to microscopic analysis or comparison. Chemical hair analysis may be considered for retrospective purposes when blood and urine are no longer expected to contain a particular contaminant, typically three months or less.

A drug test is a technical analysis of a biological specimen, for example urine, hair, blood, breath, sweat, or oral fluid/saliva—to determine the presence or absence of specified parent drugs or their metabolites. Major applications of drug testing include detection of the presence of performance enhancing steroids in sport, employers and parole/probation officers screening for drugs prohibited by law and police officers testing for the presence and concentration of alcohol (ethanol) in the blood commonly referred to as BAC. BAC tests are typically administered via a breathalyzer while urinalysis is used for the vast majority of drug testing in sports and the workplace. Numerous other methods with varying degrees of accuracy, sensitivity, and detection periods exist.

<span class="mw-page-title-main">Forensic toxicology</span> Use of toxicology for investigations

Forensic toxicology is a multidisciplinary field that combines the principles of toxicology with expertise in disciplines such as analytical chemistry, pharmacology and clinical chemistry to aid medical or legal investigation of death, poisoning, and drug use. The paramount focus for forensic toxicology is not the legal implications of the toxicological investigation or the methodologies employed, but rather the acquisition and accurate interpretation of results. Toxicological analyses can encompass a wide array of samples. In the course of an investigation, a forensic toxicologist must consider the context of an investigation, in particular any physical symptoms recorded, and any evidence collected at a crime scene that may narrow the search, such as pill bottles, powders, trace residue, and any available chemicals. Armed with this contextual information and samples to examine, the forensic toxicologist is tasked with identifying the specific toxic substances present, quantifying their concentrations, and assessing their likely impact on the individual involved.

<span class="mw-page-title-main">Cocaethylene</span> Chemical compound

Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In 1885, cocaethylene was first synthesized, and in 1979, cocaethylene's side effects were discovered.

<span class="mw-page-title-main">Dimethocaine</span> Stimulant

Dimethocaine, also known as DMC or larocaine, is a compound with a stimulatory effect. This effect resembles that of cocaine, although dimethocaine appears to be less potent. Just like cocaine, dimethocaine is addictive due to its stimulation of the reward pathway in the brain. However, dimethocaine is a legal cocaine replacement in some countries and is even listed by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) under the category “synthetic cocaine derivatives”. The structure of dimethocaine, being a 4-aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature.

<span class="mw-page-title-main">11-Nor-9-carboxy-THC</span> Main secondary metabolite of THC

11-Nor-9-carboxy-Δ9-tetrahydrocannabinol, often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<span class="mw-page-title-main">Contaminated currency</span>

Most banknotes have traces of cocaine on them; this has been confirmed by studies done in several countries. In 1994, the U.S. 9th Circuit Court of Appeals determined that in Los Angeles, out of every four banknotes, on average more than three are tainted by cocaine or another illicit drug.

<span class="mw-page-title-main">Ethyl glucuronide</span> Chemical compound

Ethyl glucuronide (EtG) is a metabolite of ethanol which is formed in the body by glucuronidation following exposure to ethanol, usually from drinking alcoholic beverages. It is used as a biomarker to test for ethanol use and to monitor alcohol abstinence in situations where drinking is prohibited, such as by the military, in alcohol treatment programs, in professional monitoring programs, in schools, liver transplant clinics, or in recovering alcoholic patients. In addition to its use to monitor abstinence and detect drinking, EtG also has potential for monitoring the amount of alcohol use over time because it can be detected in hair and nails, though the effectiveness of this has not yet been proven.

<span class="mw-page-title-main">Famprofazone</span> NSAID analgesic medication

Famprofazone is a nonsteroidal anti-inflammatory agent (NSAID) of the pyrazolone series which is available over-the-counter in some countries such as Taiwan. It has analgesic, anti-inflammatory, and antipyretic effects. Famprofazone has been known to produce methamphetamine as an active metabolite, with 15–20% of an oral dose being converted to it. As a result, famprofazone has occasionally been implicated in causing positives on drug tests for amphetamines.

<span class="mw-page-title-main">Cannabis drug testing</span> Drug test methodologies for the use of cannabis

Cannabis drug testing describes various drug test methodologies for the use of cannabis in medicine, sport, and law. Cannabis use is highly detectable and can be detected by urinalysis, hair analysis, as well as saliva tests for days or weeks.

<span class="mw-page-title-main">Flubromazepam</span> Benzodiazepine designer drug

Flubromazepam is a benzodiazepine derivative which was first synthesized in 1960, but was never marketed and did not receive any further attention or study until late 2012 when it appeared on the grey market as a novel designer drug.

<span class="mw-page-title-main">NPDPA</span> Chemical compound

NPDPA is a dissociative anesthetic that has been sold online as a designer drug. It was first identified in Germany in 2008, and while it has never been as widely sold as related compounds such as diphenidine and ephenidine, it has continued to show up in seized drug samples occasionally, and was banned in Sweden in 2015.

<span class="mw-page-title-main">MDMB-4en-PINACA</span> Chemical compound

MDMB-4en-PINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. MDMB-4en-PINACA was first identified in Europe in 2017. In 2021, MDMB-4en-PINACA was the most common synthetic cannabinoid identified by the Drug Enforcement Administration in the United States. MDMB-4en-PINACA differs from 5F-MDMB-PINACA due to replacement of 5-fluoropentyl with a pent-4-ene moiety (4-en).

<span class="mw-page-title-main">ADB-BINACA</span> Chemical compound

ADB-BINACA (also known as ADMB-BZINACA using EMCDDA naming standards) is a cannabinoid designer drug that has been found as an ingredient in some synthetic cannabis products. It was originally developed by Pfizer as a potential analgesic, and is a potent agonist of the CB1 receptor with a binding affinity (Ki) of 0.33 nM and an EC50 of 14.7 nM.

<span class="mw-page-title-main">ADB-BUTINACA</span> Chemical compound

ADB-BUTINACA (also known as ADMB-BINACA using EMCDDA naming standards) is a synthetic cannabinoid compound which has been sold as a designer drug. It is a potent CB1 agonist, with a binding affinity of 0.29nM for CB1 and 0.91nM for CB2, and an EC50 of 6.36 nM for CB1.

<span class="mw-page-title-main">Butyrylnorfentanyl</span> Synthetic opioid analgesic metabolite

Butyrnorfentanyl or butyrylnorfentanyl is an inactive synthetic opioid analgesic drug precursor. It is an analog of fentanyl.

<span class="mw-page-title-main">Furanyl norfentanyl</span> Synthetic opioid analgesic metabolite

Furanylnorfentanyl is an inactive synthetic opioid analgesic drug precursor. It is an analog of fentanyl.

<span class="mw-page-title-main">Norfentanyl</span> Synthetic opioid analgesic metabolite and precursor

Norfentanyl is an inactive synthetic opioid analgesic drug precursor. It is an analog and metabolite of fentanyl with the removal of the phenethyl moiety from fentanyl chemical structure.

References

  1. "Virtual Mass Spectrometry Laboratory: Cocaine in Hair". Archived from the original on 2007-09-01. Retrieved 2008-01-14.
  2. 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.
  3. Just WW, Hoyer J (January 1977). "The local anesthetic potency of norcocaine, a metabolite of cocaine". Experientia. Birkhäuser. 33 (1): 70–1. doi:10.1007/BF01936761. PMID   836425. S2CID   32483810.
  4. 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.
  5. 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.
  6. "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.
  7. B.S, Amanda Stevens (2022-06-05). "Symptoms & Risks Of Cocaine Use & Abuse" . Retrieved 2023-04-15.
  8. "Norcocaine". sigmaaldrich.com. Sigma-Aldrich Co. LLC. Retrieved 8 December 2014.
  9. 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.
  10. 1 2 3 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.
  11. 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.
  12. Baumgartner WA, Hill VA (1992). "Hair analysis for drugs of abuse: Decontamination issues". Recent Developments in Therapeutic Drug Monitoring and Clinical Toxicology.
  13. 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.
  14. 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.
  15. 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.
  16. 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.