Page last updated: 2024-09-27

norcocaine

Description

norcocaine: N-demethylated cocaine; RN given refers to (1R-(exo,exo))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID644007
CHEBI ID178585
SCHEMBL ID328855
MeSH IDM0052720

Synonyms (21)

Synonym
methyl (1r,2r,3s,5s)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2-carboxylate
CHEBI:178585
1-alpha-h,5-alpha-h-nortropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester)
norcocaine
8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-, methyl ester, [1r-(exo,exo)]-
18717-72-1
1alphah,5alphah-nortropane-2beta-carboxylic acid, 3beta-hydroxy-, methyl ester, benzoate (ester) (8ci)
(-)-norcocaine
8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-, methyl ester, (1r,2r,3s,5s)- (9ci)
unii-3sl7br2m1e
3sl7br2m1e ,
n-demethylcocaine
SCHEMBL328855
methyl (1r,2r,3s,5s)-3-(benzoyloxy)-8-azabicyclo(3.2.1)octane-2-carboxylate
8-azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-, methyl ester, (1r,2r,3s,5s)-
8-azabicyclo[3.2.1]octane-2-carboxylicacid,3-(benzoyloxy)-,methyl ester,(1r,2r,3s,5s)-
AYDBLCSLKNTEJL-RFQIPJPRSA-N
DTXSID80912319
Q7050488
8-azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-, methyl ester, (1r,2r,3s,5s)-
norcocaine (hydrochloride)

Treatment

ExcerptReference
"Norcocaine treatments also resulted in significant correlations between ANP or NT-ANP levels and haemodynamic variables, especially between the right atrial pressure and the plasma immunoreactive ANP levels (r = 0.58, n = 28, P < 0.005)."( Huttunen, P; MacDonald, E; Mahlakaarto, J; Pasanen, M; Ruskoaho, H, 1998)

Drug Classes (1)

ClassDescription
benzoate esterEsters of benzoic acid or substituted benzoic acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (118)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (18.64)18.7374
1990's49 (41.53)18.2507
2000's19 (16.10)29.6817
2010's25 (21.19)24.3611
2020's3 (2.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.75%)5.53%
Reviews2 (1.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other130 (97.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (8)

ArticleYear
In vivo characterization of toxicity of norcocaethylene and norcocaine identified as the most toxic cocaine metabolites in male mice.
Drug and alcohol dependence, 11-01, Volume: 204
2019
Role of oxidative metabolites of cocaine in toxicity and addiction: oxidative stress and electron transfer.
Medical hypotheses, Volume: 64, Issue: 2
2005
The comparative toxicity of cocaine and its metabolites in conscious rats.
Anesthesiology, Volume: 90, Issue: 6
1999
Role of gender in the toxicity of norcocaine.
The Journal of laboratory and clinical medicine, Volume: 133, Issue: 6
1999
Effect of cytochrome P450 inducers on cocaine-mediated hepatotoxicity.
Toxicology and applied pharmacology, Volume: 150, Issue: 1
1998
Cocaine toxicity in cultured chicken hepatocytes: role of cytochrome P450.
Toxicology and applied pharmacology, Volume: 125, Issue: 2
1994
Lethal toxicity from equimolar infusions of cocaine and cocaine metabolites in conscious and anesthetized rats.
Anesthesia and analgesia, Volume: 81, Issue: 5
1995
Cocaine-induced hepatotoxicity: lipid peroxidation as a possible mechanism.
Drug and chemical toxicology, Volume: 7, Issue: 4
1984
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (1)

ArticleYear
Single hair cocaine consumption monitoring by mass spectrometric imaging.
Analytical chemistry, Jun-01, Volume: 83, Issue: 11
2011
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (10)

ArticleYear
Estrogen and progesterone affect cocaine pharmacokinetics in female rats.
Brain research bulletin, Jan-30, Volume: 68, Issue: 5
2006
Simultaneous pharmacokinetic modeling of cocaine and its metabolites, norcocaine and benzoylecgonine, after intravenous and oral administration in rats.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 29, Issue: 9
2001
Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics.
Psychopharmacology, Volume: 153, Issue: 3
2001
Chronic continuous cocaine infusion in rats: effect on urine cocaine, ecgonine methylester and benzoylecgonine concentrations and bolus-dose cocaine pharmacokinetics.
The Journal of pharmacy and pharmacology, Volume: 52, Issue: 4
2000
Cocaine, norcocaine, ecgonine methylester and benzoylecgonine pharmacokinetics in the rat.
Life sciences, Volume: 65, Issue: 12
1999
Cocaine pharmacodynamics after intravenous and oral administration in rats: relation to pharmacokinetics.
Psychopharmacology, Volume: 144, Issue: 4
1999
Determination of cocaine and its metabolites in serum microsamples by high-performance liquid chromatography and its application to pharmacokinetics in rats.
Journal of chromatography. B, Biomedical sciences and applications, Jun-06, Volume: 693, Issue: 2
1997
Pharmacokinetics and effect of cocaine on cerebral blood flow in the newborn.
Developmental pharmacology and therapeutics, Volume: 20, Issue: 1-2
1993
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (3)

ArticleYear
Simultaneous pharmacokinetic modeling of cocaine and its metabolites, norcocaine and benzoylecgonine, after intravenous and oral administration in rats.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 29, Issue: 9
2001
Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics.
Psychopharmacology, Volume: 153, Issue: 3
2001
Cocaine pharmacodynamics after intravenous and oral administration in rats: relation to pharmacokinetics.
Psychopharmacology, Volume: 144, Issue: 4
1999
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (5)

ArticleYear
Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics.
Psychopharmacology, Volume: 153, Issue: 3
2001
Effects of cocaine, benzoylecgonine, and cocaine metabolites in cannulated pressurized fetal sheep cerebral arteries.
Journal of applied physiology (Bethesda, Md. : 1985), Volume: 77, Issue: 2
1994
Lethal toxicity from equimolar infusions of cocaine and cocaine metabolites in conscious and anesthetized rats.
Anesthesia and analgesia, Volume: 81, Issue: 5
1995
Intravenous self-administration of cocaine and norcocaine by dogs.
Psychopharmacology, Volume: 71, Issue: 1
1980
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]