Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H14N2 |
Molecular Weight | 162.2319 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC[C@@]1([H])c2cccnc2
InChI
InChIKey=SNICXCGAKADSCV-JTQLQIEISA-N
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
Molecular Formula | C10H14N2 |
Molecular Weight | 162.2319 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: www.inchem.org/documents/pims/chemical/nicotine.htmCurator's Comment:: description was created based on several sources, including
https://cancercontrol.cancer.gov/brp/tcrb/monographs/1/index.html
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928221/
Sources: www.inchem.org/documents/pims/chemical/nicotine.htm
Curator's Comment:: description was created based on several sources, including
https://cancercontrol.cancer.gov/brp/tcrb/monographs/1/index.html
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928221/
Nicotine is a natural alkaloid obtained from the dried leaves and stems of the nightshade family of pants, such as Nicotiana tabacum and Nicotiana rustica, where it occurs in concentrations of 0.5-8%. Cigarette tobacco varies in its nicotine content, but common blends contain 15-25 mg per cigarette, with a current trend towards lower levels. Nicotine is highly addictive substance, it exhibits a stimulant effect when adsorbed at 2 mg. Administration of higher doses could be harmful. Action of nicotine is mediated by nicotinic cholinergic receptors. Nicotine binds to the interface between two subunits of the receptors, opens the channel and allows the entry of sodium or calcium. The principal mediator of nicotine dependence is α4β2 nicotine receptor.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443 |
7.9 null [pKi] | ||
Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173 |
260.0 nM [Ki] | ||
Target ID: CHEMBL2492 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15528443 |
3.0 µM [Ki] | ||
Target ID: CHEMBL2109238 |
|||
Target ID: Nicotinic acetylcholine receptors |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | NICORETTE Approved UseReduces withdrawal symptoms, including nicotine craving associated with quitting smoking Launch Date4.42713604E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 ng/mL |
1 mg single, nasal dose: 1 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NICOTINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 ng × h/mL |
1 mg single, nasal dose: 1 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NICOTINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3 min |
1 mg single, nasal dose: 1 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NICOTINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95% |
1 mg single, nasal dose: 1 mg route of administration: Nasal experiment type: SINGLE co-administered: |
NICOTINE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
6 mg single, oral Highest studied dose |
healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: |
Disc. AE: Bradycardia... AEs leading to discontinuation/dose reduction: Bradycardia (1 patient) Sources: |
4 mg single, oral Studied dose |
healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: |
Disc. AE: Allergic dermatitis... AEs leading to discontinuation/dose reduction: Allergic dermatitis (1 patient) Sources: |
6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Disc. AE: Hypersensitivity, Nausea... AEs leading to discontinuation/dose reduction: Hypersensitivity (1 patient) Sources: Nausea (1 patient) |
8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Disc. AE: Depression, Nausea... AEs leading to discontinuation/dose reduction: Depression (1 patient) Sources: Nausea (grade 2-3, 2 patients) |
111 mg single, transdermal Overdose Dose: 111 mg Route: transdermal Route: single Dose: 111 mg Sources: |
healthy, 41 years n = 1 Health Status: healthy Condition: adult smoker Age Group: 41 years Sex: M Population Size: 1 Sources: |
Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: |
84 mg 1 times / day steady, transdermal Highest studied dose Dose: 84 mg, 1 times / day Route: transdermal Route: steady Dose: 84 mg, 1 times / day Sources: |
healthy, adult n = 36 Health Status: healthy Condition: adult smokers Age Group: adult Sex: unknown Population Size: 36 Sources: |
Other AEs: Nausea... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bradycardia | 1 patient Disc. AE |
6 mg single, oral Highest studied dose |
healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: |
Allergic dermatitis | 1 patient Disc. AE |
4 mg single, oral Studied dose |
healthy, 19 - 49 years n = 44 Health Status: healthy Condition: adult smokers Age Group: 19 - 49 years Sex: M+F Population Size: 44 Sources: |
Hypersensitivity | 1 patient Disc. AE |
6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Nausea | 1 patient Disc. AE |
6 mg 1 times / hour steady, oral Highest studied dose Dose: 6 mg, 1 times / hour Route: oral Route: steady Dose: 6 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Depression | 1 patient Disc. AE |
8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Nausea | grade 2-3, 2 patients Disc. AE |
8 mg 1 times / hour steady, oral Highest studied dose Dose: 8 mg, 1 times / hour Route: oral Route: steady Dose: 8 mg, 1 times / hour Sources: |
healthy, 19 - 50 years n = 50 Health Status: healthy Condition: adult smokers Age Group: 19 - 50 years Sex: M+F Population Size: 50 Sources: |
Death | grade 5, 1 patient Disc. AE |
111 mg single, transdermal Overdose Dose: 111 mg Route: transdermal Route: single Dose: 111 mg Sources: |
healthy, 41 years n = 1 Health Status: healthy Condition: adult smoker Age Group: 41 years Sex: M Population Size: 1 Sources: |
Nausea | 84 mg 1 times / day steady, transdermal Highest studied dose Dose: 84 mg, 1 times / day Route: transdermal Route: steady Dose: 84 mg, 1 times / day Sources: |
healthy, adult n = 36 Health Status: healthy Condition: adult smokers Age Group: adult Sex: unknown Population Size: 36 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 245.0 |
minor | |||
Page: 245.0 |
minor | |||
Sources: https://molpharm.aspetjournals.org/content/72/3/761 Page: - |
no | |||
Page: - |
yes | |||
Page: 245.0 |
yes | |||
Page: - |
yes | |||
Page: 60.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/17909004/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/20876810/ Page: - |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Modulation of phosphatidylinositol turnover on central nicotinic receptors. | 1997 Jul |
|
Nicotine potentiates sulpiride-induced catalepsy in mice. | 1998 |
|
Ginseng total saponin inhibits nicotine-induced hyperactivity and conditioned place preference in mice. | 1999 Jul |
|
Predictors and timing of adverse experiences during trandsdermal nicotine therapy. | 1999 Jun |
|
Selective alpha 7 nicotinic receptor stimulation normalizes chronic cocaine-induced loss of hippocampal sensory inhibition in C3H mice. | 1999 Nov 15 |
|
Mimicking gene defects to treat drug dependence. | 2000 |
|
Analgesic and toxic effects of ABT-594 resemble epibatidine and nicotine in rats. | 2000 Apr |
|
Transdermal nicotine mimics the smoking-induced endothelial dysfunction. | 2000 Aug |
|
Deficient cotinine formation from nicotine is attributed to the whole deletion of the CYP2A6 gene in humans. | 2000 Jan |
|
Regional and cellular induction of nicotine-metabolizing CYP2B1 in rat brain by chronic nicotine treatment. | 2000 Jun 15 |
|
[A comparative study of the central H-cholinergic-blocking and NMDA-blocking actions of MK-801, memantin, amantadine, pyrilen and IEM-1754 in experiments on intact rats]. | 2000 Mar-Apr |
|
Kynurenic acid does not protect against nicotine-induced seizures in mice. | 2000 Nov-Dec |
|
Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats. | 2000 Oct |
|
Duplications and defects in the CYP2A6 gene: identification, genotyping, and in vivo effects on smoking. | 2000 Oct |
|
Evidence that nicotinic alpha(7) receptors are not involved in the hyperlocomotor and rewarding effects of nicotine. | 2000 Sep |
|
Effect of nicotine on fibroblast beta 1 integrin expression and distribution in vitro. | 2001 Apr |
|
Nicotine inhibits UV-induced activation of the apoptotic pathway. | 2001 Dec 15 |
|
Tolerance to nicotine's effects in the elevated plus-maze and increased anxiety during withdrawal. | 2001 Feb |
|
Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats. | 2001 Jan |
|
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. | 2001 Jun |
|
Reversal of diminished inhibitory sensory gating in cocaine addicts by a nicotinic cholinergic mechanism. | 2001 Jun |
|
Smoking and balance: correlation of nicotine-induced nystagmus and postural body sway. | 2001 May 8 |
|
Comparison of cytochrome P450 2A6 polymorphism frequencies in Caucasians and African-Americans using a new one-step PCR-RFLP genotyping method. | 2001 Nov 30 |
|
Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine. | 2001 Sep |
|
Microsomal N-glucuronidation of nicotine and cotinine: human hepatic interindividual, human intertissue, and interspecies hepatic variation. | 2002 Dec |
|
Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor. | 2002 Feb 11 |
|
Enhancement of cocaine-seeking behavior by repeated nicotine exposure in rats. | 2002 Jul |
|
Involvement of human heat shock protein 90 alpha in nicotine-induced apoptosis. | 2002 Jul 1 |
|
The selectively bred high alcohol sensitivity (HAS) and low alcohol sensitivity (LAS) rats differ in sensitivity to nicotine. | 2002 Jun |
|
N-n-alkylnicotinium analogs, a novel class of nicotinic receptor antagonist: inhibition of S(-)-nicotine-evoked [(3)H]dopamine overflow from superfused rat striatal slices. | 2002 Jun |
|
Increased sensitivity to nicotine-induced seizures in mice expressing the L250T alpha 7 nicotinic acetylcholine receptor mutation. | 2002 Mar |
|
Nicotine potentiation of morphine-induced catalepsy in mice. | 2002 May |
|
Genetic polymorphisms in human CYP2A6 gene causing impaired nicotine metabolism. | 2002 Nov |
|
CYP2A6 genetic variation and potential consequences. | 2002 Nov 18 |
|
beta 2 nicotinic acetylcholine receptor subunit modulates protective responses to stress: A receptor basis for sleep-disordered breathing after nicotine exposure. | 2002 Oct 1 |
|
N-glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases. | 2002 Sep |
|
Oral caffeine maintenance potentiates the reinforcing and stimulant subjective effects of intravenous nicotine in cigarette smokers. | 2003 Jan |
|
Nicotinic acetylcholine receptors and the regulation of neuronal signalling. | 2004 Jun |
|
How much nicotine kills a human? Tracing back the generally accepted lethal dose to dubious self-experiments in the nineteenth century. | 2014 Jan |
Patents
Sample Use Guides
Reduces withdrawal symptoms, including nicotine craving associated with quitting smoking, nicotine is available as a chewing gum, and is administered according to a schedule at doses 2-4 mg once every 2-4 hours. Nicotine is also available as a transdermal patch.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22148173
Functional activity of nicotine against hα4β2 nicotinic receptors was evaluated using the 86Rb+ ion flux assay in SH-EP1 cells, expressing hα4β2. The 86Rb+ efflux was measured using the “flip-plate” technique. Nicotine activated 86Rb+ efflux with EC50 of 290 nM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:58:06 UTC 2021
by
admin
on
Fri Jun 25 20:58:06 UTC 2021
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Record UNII |
6M3C89ZY6R
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C221
Created by
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LIVERTOX |
683
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WHO-ATC |
N07BA01
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NDF-RT |
N0000175706
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WHO-VATC |
QP53AX13
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WHO-VATC |
QN07BA01
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EPA PESTICIDE CODE |
56702
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NDF-RT |
N0000006496
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NCI_THESAURUS |
C73579
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NDF-RT |
N0000006496
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Code System | Code | Type | Description | ||
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D009538
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7407
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2585
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C691
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89594
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1107
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NICOTINE
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CHEMBL3
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DB00184
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54-11-5
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SUB14645MIG
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Nicotine
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54-11-5
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SUB30160
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1920
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M7879
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PRIMARY | Merck Index | ||
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6M3C89ZY6R
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200-193-3
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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TARGET -> AGONIST |
NICOTINE IS AN ANTIHERBIVORY ALKALOID AND POTENT PARASYMPATHOMIMETIC STIMULANT AND FOUND IN PLANTS, MOSTLY THOSE IN THE NIGHTSHADE FAMILY. NICOTINE ACTS AS A RECEPTOR AGONIST AT MOST NICOTINIC ACETYLCHOLINE RECEPTORS (NACHRS), EXCEPT AT TWO NICOTINIC RECEPTOR SUBUNITS (NACHR.ALPHA.9 AND NACHR.ALPHA.10) WHERE IT ACTS AS A RECEPTOR ANTAGONIST.
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SUB_CONCEPT->SUBSTANCE | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Nicotine (mg/cigarette)
Domestic = 12.6 SD(1.6)
Imported = 11.1 SD(2.2)
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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LABELED -> NON-LABELED | |||
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SUB_CONCEPT->SUBSTANCE |
Related Record | Type | Details | ||
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METABOLITE LESS ACTIVE -> PARENT |
75% is converted into cotintine which is further metabolized.
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
circulating nicotine is metabolized to cotinine by cytochrome P450 and aldehyde oxidase
MAJOR
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METABOLITE -> PARENT |
in animals both N-oxide isomers form, in humans only the transisomers form.
MAJOR
URINE
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METABOLITE -> PARENT |
The extent of nicotine N-glucuronidation by African Americans is significantly lower than by Whites.
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METABOLITE -> PARENT |
PLASMA; URINE
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METABOLITE -> PARENT |
The extent of Cotinine N-glucuronidation by African Americans is significantly lower than by Whites.
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METABOLITE INACTIVE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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