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:: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2928221/
Sources: www.inchem.org/documents/pims/chemical/nicotine.htm
Curator's Comment:: 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 |
7.90000000000000036 null [pKi] | ||
Target ID: CHEMBL1907594 |
260 nM [Ki] | ||
Target ID: CHEMBL2492 |
3 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 Date442713600000 |
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 Health Status: healthy Age Group: 19 - 49 years Sex: M+F Sources: |
Disc. AE: Bradycardia... AEs leading to discontinuation/dose reduction: Bradycardia (1 patient) Sources: |
4 mg single, oral Studied dose |
healthy, 19 - 49 years Health Status: healthy Age Group: 19 - 49 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 |
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 Health Status: healthy Age Group: adult Sex: unknown 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 Health Status: healthy Age Group: 19 - 49 years Sex: M+F Sources: |
| Allergic dermatitis | 1 patient Disc. AE |
4 mg single, oral Studied dose |
healthy, 19 - 49 years Health Status: healthy Age Group: 19 - 49 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 Health Status: healthy Age Group: 19 - 50 years Sex: M+F 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 |
| 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 Health Status: healthy Age Group: adult Sex: unknown Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: - |
no | |||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| minor | ||||
| minor | ||||
Page: - |
no | |||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cow's urine poisoning in Nigeria. Experimental observations in mice. | 1975 Jun |
|
| Abstinence effects and reactivity to nicotine during 11 days of smoking deprivation. | 2000 May |
|
| Involvement of 5-hydroxytryptamine(1A) receptors in nicotine-induced tail tremor in rats. | 2000 Nov 10 |
|
| Nicotine-induced nystagmus: three-dimensional analysis and dependence on head position. | 2000 Nov 28 |
|
| Kynurenic acid does not protect against nicotine-induced seizures in mice. | 2000 Nov-Dec |
|
| Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. | 2000 Oct |
|
| Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats. | 2000 Oct |
|
| Formation of the quaternary ammonium-linked glucuronide of nicotine in human liver microsomes: identification and stereoselectivity in the kinetics. | 2001 Dec |
|
| Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices. | 2001 Dec 15 |
|
| Tolerance to nicotine's effects in the elevated plus-maze and increased anxiety during withdrawal. | 2001 Feb |
|
| Nicotine induced changes in gene expression by human coronary artery endothelial cells. | 2001 Feb 1 |
|
| Nicotine self-administration and withdrawal: modulation of anxiety in the social interaction test in rats. | 2001 Jan |
|
| Relationship between interindividual differences in nicotine metabolism and CYP2A6 genetic polymorphism in humans. | 2001 Jan |
|
| Cardiovascular effects of transdermal nicotine in mildly hypertensive smokers. | 2001 Jul |
|
| Nicotine produces selective degeneration in the medial habenula and fasciculus retroflexus. | 2001 Jul 6 |
|
| Nicotine metabolism and CYP2A6 allele frequencies in Koreans. | 2001 Jun |
|
| Nicotinic regulation of c-fos and osteopontin expression in human-derived osteoblast-like cells and human trabecular bone organ culture. | 2001 Jun |
|
| 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 |
|
| A novel single nucleotide polymorphism altering stability and activity of CYP2a6. | 2001 Mar 2 |
|
| Inhibition of nicotine-induced seizures in rats by combining vaccination against nicotine with chronic nicotine infusion. | 2001 May |
|
| 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 |
|
| Chronic ethanol and nicotine interaction on rat tissue antioxidant defense system. | 2001 Oct |
|
| Nicotine induced seizures blocked by mecamylamine and its stereoisomers. | 2001 Oct 19 |
|
| Activation of 5-HT(2C) receptors reduces the locomotor and rewarding effects of nicotine. | 2001 Sep |
|
| Acute myocardial infarction soon after nicotine replacement therapy. | 2001 Sep |
|
| Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco. | 2001 Sep 21 |
|
| Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum. | 2001 Sep 28 |
|
| Fetal and adolescent nicotine administration: effects on CNS serotonergic systems. | 2001 Sep 28 |
|
| Molecular orbital calculations and nicotine metabolism: a rationale for experimentally observed metabolite ratios. | 2002 |
|
| Mechanisms of cytotoxicity of nicotine in human periodontal ligament fibroblast cultures in vitro. | 2002 Aug |
|
| The relationship between hippocampal acetylcholine release and cholinergic convulsant sensitivity in withdrawal seizure-prone and withdrawal seizure-resistant selected mouse lines. | 2002 Aug |
|
| Alcohol and nicotine reduce cell proliferation and enhance apoptosis in dentate gyrus. | 2002 Aug 27 |
|
| Genetic variation in CYP2A6-mediated nicotine metabolism alters smoking behavior. | 2002 Feb |
|
| Increased sensitivity to nicotine-induced seizures in mice heterozygous for the L250T mutation in the alpha7 nicotinic acetylcholine receptor. | 2002 Feb 11 |
|
| An in vivo pilot study characterizing the new CYP2A6*7, *8, and *10 alleles. | 2002 Jan 11 |
|
| Absence of alpha7-containing neuronal nicotinic acetylcholine receptors does not prevent nicotine-induced seizures. | 2002 Jan 31 |
|
| 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 |
|
| Increased sensitivity to nicotine-induced seizures in mice expressing the L250T alpha 7 nicotinic acetylcholine receptor mutation. | 2002 Mar |
|
| Up-regulation of L-type voltage-dependent calcium channels after long term exposure to nicotine in cerebral cortical neurons. | 2002 Mar 8 |
|
| Effects of whole deletion of CYP2A6 on nicotine metabolism in humans. | 2002 May |
|
| 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 |
|
| Lasting effects of adolescent nicotine exposure on the electroencephalogram, event related potentials, and locomotor activity in the rat. | 2002 Sep 20 |
|
| Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
| Nicotinic acetylcholine receptors and the regulation of neuronal signalling. | 2004 Jun |
|
| Nicotine addiction. | 2010 Jun 17 |
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
| 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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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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NCI_THESAURUS |
C221
Created by
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LIVERTOX |
683
Created by
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WHO-ATC |
N07BA01
Created by
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NDF-RT |
N0000175706
Created by
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WHO-VATC |
QP53AX13
Created by
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WHO-VATC |
QN07BA01
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EPA PESTICIDE CODE |
56702
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NDF-RT |
N0000006496
Created by
admin on Fri Jun 25 20:58:06 UTC 2021 , Edited by admin on Fri Jun 25 20:58:06 UTC 2021
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NCI_THESAURUS |
C73579
Created by
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NDF-RT |
N0000006496
Created by
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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
Created by
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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 | |||
|
SALT/SOLVATE -> PARENT | |||
|
BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SUB_CONCEPT->SUBSTANCE | |||
|
SALT/SOLVATE -> PARENT | |||
|
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 |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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| Volume of Distribution | PHARMACOKINETIC |
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