Compounds > norcotinine
Page last updated: 2024-12-04

norcotinine

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

Description

norcotinine: RN given refers to compound without isomeric designation; metabolite of cotinine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID413
CHEMBL ID3126030
CHEBI ID89406
SCHEMBL ID2788897
MeSH IDM0182064

Synonyms (30)

Synonym
5-(3-pyridinyl)-2-pyrrolidinone
norcotinine
(r,s)-norcotinine
17708-87-1
5-pyridin-3-ylpyrrolidin-2-one
AKOS006278969
2-pyrrolidinone, 5-(3-pyridinyl)-
17114-40-8
FT-0673062
FT-0673063
chebi:89406 ,
CHEMBL3126030
SCHEMBL2788897
desmethylcotinine
FXFANIORDKRCCA-UHFFFAOYSA-N
5-(pyridin-3-yl)pyrrolidin-2-one
rac-norcotinine
(rs)-norcotinine; 2-pyrrolidinone, 5-(3-pyridinyl)-, (+/-)-; norcotinine, (+/-)- (8ci); (+/-)-demethylcotinine; (+/-)-norcotinine
(5rs)-5-(pyridin-3-yl)pyrrolidin-2-one ((rs)-norcotinine)
rac-norcotinine 1.0 mg/ml in methanol
J-011252
(rs)-norcotinine
DTXSID10864736
Q27161596
chlorambenmethylester
5-pyridin-3-yl-pyrrolidin-2-one
SB34310
SB31675
SB37864
(r)-5-pyridin-3-yl-pyrrolidin-2-one

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" However, other compounds metabolized by CYP2A6, as well as other drugs excreted via renal clearance mechanisms similar to those of nicotine, may be susceptible to significant pharmacokinetic grapefruit juice interactions."( Effect of grapefruit juice on cytochrome P450 2A6 and nicotine renal clearance.
Benowitz, NL; Hukkanen, J; Jacob, P, 2006)		0.33
" However, age-related pharmacokinetic differences may confound the interpretation of these findings."( Nicotine pharmacokinetics in rats is altered as a function of age, impacting the interpretation of animal model data.
Craig, EL; Cui, JZ; Miksys, S; Novalen, M; Tyndale, RF; Zhao, B, 2014)		0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
pyrrolidinesAny of a class of heterocyclic amines having a saturated five-membered ring.
pyridinesAny organonitrogen heterocyclic compound based on a pyridine skeleton and its substituted derivatives.
[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]

Pathways (3)

PathwayProteinsCompounds
Nicotine Action Pathway3832
Nicotine Metabolism Pathway923
Nicotine Pathway, Pharmacokinetics129

Bioassays (11)

Assay IDTitleYearJournalArticle
AID1076771Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 100 nM pretreated for 24 hrs followed by amyloid beta 1 to 42 challenge measured after 22014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076766Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of glutamate-induced toxicity by measuring cell viability at 1 uM pretreated for 24 hrs followed by glutamate challenge measured after 24 hrs by MTT assay relat2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076775Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 100 uM pretreated for 24 hrs followed by amyloid beta 1 to 42 challenge measured after 22014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076770Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 1 uM pretreated for 24 hrs followed by amyloid beta 1 to 42 challenge measured after 24 2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076773Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 100 uM by trypan blue exclusion assay2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076768Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of glutamate-induced toxicity by measuring cell viability at 10 nM pretreated for 24 hrs followed by glutamate challenge measured after 24 hrs by MTT assay rela2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076769Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 10 uM pretreated for 24 hrs followed by amyloid beta 1 to 42 challenge measured after 242014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076767Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of glutamate-induced toxicity by measuring cell viability at 100 nM pretreated for 24 hrs followed by glutamate challenge measured after 24 hrs by MTT assay rel2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076772Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of amyloid beta 1 to 42-induced toxicity by measuring cell viability at 10 nM pretreated for 24 hrs followed by amyloid beta 1 to 42 challenge measured after 242014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076765Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of glutamate-induced toxicity by measuring cell viability at 10 uM pretreated for 24 hrs followed by glutamate challenge measured after 24 hrs by MTT assay rela2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
AID1076764Neuroprotective activity in Sprague-Dawley rat primary cortical neurons assessed as inhibition of glutamate-induced toxicity by measuring cell viability at 100 uM pretreated for 24 hrs followed by glutamate challenge measured after 24 hrs by MTT assay rel2014Bioorganic & medicinal chemistry letters, Mar-15, Volume: 24, Issue:6
Evaluation of nicotine and cotinine analogs as potential neuroprotective agents for Alzheimer's disease.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.26)18.7374
1990's4 (21.05)18.2507
2000's6 (31.58)29.6817
2010's7 (36.84)24.3611
2020's1 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.53

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index23.53 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (4.76%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (95.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
nicotine 1-n-oxide
nicotine 1-N-oxide: RN given refers to unspecified stereoisomer. nicotine N(1')-oxide : A tertiary amine oxide resulting from the oxidation of the pyrrolidine nitrogen of nicotine.		2.4920pyridines;
pyrrolidine N-oxides
nornicotine
nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure		3.82110
donepezil
Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.		2.110aromatic ether;
indanones;
piperidines;
racemate		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent
mecamylamine
Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.		7.0710primary aliphatic amine
memantine
[no description available]		2.110adamantanes;
primary aliphatic amine		antidepressant;
antiparkinson drug;
dopaminergic agent;
neuroprotective agent;
NMDA receptor antagonist
phenobarbital
Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.		1.9710barbituratesanticonvulsant;
drug allergen;
excitatory amino acid antagonist;
sedative
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.110benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
anatabine
anatabine: alkaloid found in tobacco; structure		2.110bipyridines
deuterium
Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.		3.4111dihydrogen
pyrrolidine
[no description available]		1.9710azacycloalkane;
pyrrolidines;
saturated organic heteromonocyclic parent
rivastigmine
[no description available]		2.110carbamate ester;
tertiary amino compound		cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent
nicotine
(S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.		5.711913-(1-methylpyrrolidin-2-yl)pyridineanxiolytic drug;
biomarker;
immunomodulator;
mitogen;
neurotoxin;
nicotinic acetylcholine receptor agonist;
peripheral nervous system drug;
phytogenic insecticide;
plant metabolite;
psychotropic drug;
teratogenic agent;
xenobiotic
hydroxycotinine
hydroxycotinine: metabolite of nicotine; RN given refers to (S)-isomer; structure. trans-3-hydroxycotinine : An N-alkylpyrrolidine that is cotinine substituted at position C-3 by a hydroxy group (the 3R,5S-diastereomer).		5.38131N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid
cotinine-n-oxide
cotinine-N-oxide: metabolite of nicotine; structure		2.7230
pseudonicotine
pseudonicotine: structure. (R)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has R-configuration.		2.1103-(1-methylpyrrolidin-2-yl)pyridine
anabasine
Anabasine: A piperidine botanical insecticide.. (S)-anabasine : The (S)-enantiomer of anabasine.. anabasine : A pyridine alkaloid that is pyridine substituted by a piperidin-2-yl group at position 3.		2.5520anabasine
cotinine
Cotinine: The N-glucuronide conjugate of cotinine is a major urinary metabolite of NICOTINE. It thus serves as a biomarker of exposure to tobacco SMOKING. It has CNS stimulating properties.. (-)-cotinine : An N-alkylpyrrolidine that consists of N-methylpyrrolidinone bearing a pyridin-3-yl substituent at position C-5 (the 5S-enantiomer). It is an alkaloid commonly found in Nicotiana tabacum.		5.71191N-alkylpyrrolidine;
pyridines;
pyrrolidin-2-ones;
pyrrolidine alkaloid		antidepressant;
biomarker;
human xenobiotic metabolite;
plant metabolite
nicotine n-glucuronide
nicotine N-glucuronide: a metabolite of nicotine. (S)-nicotinium N-alpha-D-glucosiduronate : An N-glycosylpyridine that is the N-alpha-D-glucosiduronyl derivative of (S)-nicotine.		2.0410iminium betaine;
N-glycosylpyridine		metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Acute Confusional Senile Dementia
[description not available]		02.110
Alzheimer Disease
A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)		02.110
Smoking Cessation
Discontinuing the habit of SMOKING.		02.5320
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		02.0810
HIV Coinfection
[description not available]		02.110
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		02.110
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.4420
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.9640