Page last updated: 2024-12-09

norcocaine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

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)

Research Excerpts

Treatment

ExcerptReferenceRelevance
"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)."( Norcocaine is a potent modulator of haemodynamic responses, plasma catecholamines and cardiac hormone release in conscious rats.
Huttunen, P; MacDonald, E; Mahlakaarto, J; Pasanen, M; Ruskoaho, H, 1998
)
2.46

Toxicity

benzoylecgonine and ecgonine methyl ester are not as toxic as cocaine, norcocaine, or cocaethylene when administered intravenously to pharmacologically naive rats.

ExcerptReferenceRelevance
"Cocaine, norcocaine, cocaethylene, benzoylecgonine, and ecgonine methyl ester were infused intravenously to produce sequential behavioral alterations and central nervous system and cardiovascular toxic effects."( The comparative toxicity of cocaine and its metabolites in conscious rats.
Cooper, TB; Iso, A; Morishima, HO; Whittington, RA, 1999
)
0.72
"The dose of norcocaine necessary to produce toxic effects was smaller than that of cocaine and cocaethylene."( The comparative toxicity of cocaine and its metabolites in conscious rats.
Cooper, TB; Iso, A; Morishima, HO; Whittington, RA, 1999
)
0.68
"These results indicate that benzoylecgonine and ecgonine methyl ester are not as toxic as cocaine, norcocaine, or cocaethylene when administered intravenously to pharmacologically naive rats."( The comparative toxicity of cocaine and its metabolites in conscious rats.
Cooper, TB; Iso, A; Morishima, HO; Whittington, RA, 1999
)
0.52
" Other adverse effects associated with ROS comprise teratogenesis and apoptosis."( Role of oxidative metabolites of cocaine in toxicity and addiction: oxidative stress and electron transfer.
Kovacic, P, 2005
)
0.33
"The relative toxicity of these toxic drugs can be ranked in this order: norcocaethylene > norcocaine > cocaethylene > cocaine."( In vivo characterization of toxicity of norcocaethylene and norcocaine identified as the most toxic cocaine metabolites in male mice.
Shang, L; Zhan, CG; Zheng, F; Zheng, X, 2019
)
0.98

Pharmacokinetics

The half-life of both norcocaine and N-hydroxynorcocaine was significantly longer in DBA mice. These pharmacokinetic estimates were then used for determination of the formation of norcOCaine and benzoylecgonine after i.

ExcerptReferenceRelevance
" Although no significant differences between the strains were seen in the pharmacokinetics of cocaine, the half-life of both norcocaine and N-hydroxynorcocaine was significantly longer in DBA mice."( Pharmacokinetic analysis of the metabolism of cocaine to norcocaine and N-hydroxynorcocaine in mice.
Boyer, CS; Petersen, DR,
)
0.58
" The pharmacokinetic profile of these congeners was not dose dependent when the two doses administered were compared."( Cocaine, norcocaine, ecgonine methylester and benzoylecgonine pharmacokinetics in the rat.
Diaz, J; Jamdar, S; Mets, B; Soo, E, 1999
)
0.72
"Oral cocaine is more effective than IV cocaine by pharmacokinetic and pharmacodynamic analysis."( Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics.
Falk, JL; Lau, CE; Simpao, A; Sun, L; Wang, Q, 2001
)
0.58
" These findings suggest that while progesterone has an impact on locomotor behavior, pharmacokinetic effects may have a limited role in mediating behavioral responses to cocaine."( Estrogen and progesterone affect cocaine pharmacokinetics in female rats.
Akhavan, A; Festa, ED; Foltz, R; Lamm, L; Lin, SN; Niyomchai, T; Quiñones-Jenab, V, 2006
)
0.33

Bioavailability

ExcerptReferenceRelevance
"To investigate the absolute bioavailability of oral cocaine, its effectiveness and the relation between PK and PD in a within-subject design."( Cocaine pharmacodynamics after intravenous and oral administration in rats: relation to pharmacokinetics.
Falk, JL; Lau, CE; Ma, F, 1999
)
0.3
" The absolute oral cocaine bioavailability was determined pharmacokinetically (F) and pharmacodynamically (Fsrr and Frr)."( Cocaine pharmacodynamics after intravenous and oral administration in rats: relation to pharmacokinetics.
Falk, JL; Lau, CE; Ma, F, 1999
)
0.3

Dosage Studied

ExcerptRelevanceReference
" Cumulative dose-response curves (10(-12)-10(-4) M) were generated for cocaine and the major cocaine metabolites in fetal sheep cerebral artery segments."( Effects of cocaine, benzoylecgonine, and cocaine metabolites in cannulated pressurized fetal sheep cerebral arteries.
Covert, RF; Madden, JA; Schreiber, MD; Torgerson, LJ, 1994
)
0.29
" The changes in effects across time (effect-time profiles) and dose-response curves (DRCs) were constructed to evaluate the duration of action and potency (ED50) of both drugs."( Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics.
Falk, JL; Lau, CE; Simpao, A; Sun, L; Wang, Q, 2001
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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]

Market Indicators

Research Demand Index: 44.56

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index44.56 (24.57)
Research Supply Index4.91 (2.92)
Research Growth Index4.87 (4.65)
Search Engine Demand Index69.20 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.56)

All Compounds (24.57)

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]