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5746-86-1 | 3-(2-Pyrrolidinyl)pyridine
CAS No: 5746-86-1 Catalog No: AG00IA8O MDL No:MFCD00016913
Product Description
Catalog Number:
AG00IA8O
Chemical Name:
3-(2-Pyrrolidinyl)pyridine
CAS Number:
5746-86-1
Molecular Formula:
C9H12N2
Molecular Weight:
148.2050
MDL Number:
MFCD00016913
IUPAC Name:
3-pyrrolidin-2-ylpyridine
InChI:
InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2
InChI Key:
MYKUKUCHPMASKF-UHFFFAOYSA-N
SMILES:
C1CNC(C1)c1cccnc1
Properties
Complexity:
125
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
148.1g/mol
Formal Charge:
0
Heavy Atom Count:
11
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
148.209g/mol
Monoisotopic Mass:
148.1g/mol
Rotatable Bond Count:
1
Topological Polar Surface Area:
24.9A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
0.2
Literature
| Title | Journal |
|---|---|
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| Determination of nicotine exposure in dogs subjected to passive smoking using methanol extraction of hair followed by hydrophilic interaction chromatography in combination with Fourier transform mass spectrometry. | Talanta 20120115 |
| A one-year monitoring of nicotine use in sport: frontier between potential performance enhancement and addiction issues. | Forensic science international 20111210 |
| Validation of a liquid chromatography-tandem mass spectrometry method for the detection of nicotine biomarkers in hair and an evaluation of wash procedures for removal of environmental nicotine. | Journal of analytical toxicology 20110701 |
| Nicotine and metabolites in paired umbilical cord tissue and meconium specimens. | Therapeutic drug monitoring 20110201 |
| In silico theoretical molecular modeling for Alzheimer's disease: the nicotine-curcumin paradigm in neuroprotection and neurotherapy. | International journal of molecular sciences 20110101 |
| Three nicotine demethylase genes mediate nornicotine biosynthesis in Nicotiana tabacum L.: functional characterization of the CYP82E10 gene. | Phytochemistry 20101201 |
| A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. | Research in microbiology 20100901 |
| Extinction with varenicline and nornicotine, but not ABT-418, weakens conditioned responding evoked by the interoceptive stimulus effects of nicotine. | Neuropharmacology 20100601 |
| The analgesic and toxic effects of nornicotine enantiomers alone and in interaction with morphine in rodent models of acute and persistent pain. | Pharmacology, biochemistry, and behavior 20100101 |
| Quantitation of nicotine, its metabolites, and other related alkaloids in urine, serum, and plasma using LC-MS-MS. | Methods in molecular biology (Clifton, N.J.) 20100101 |
| The addition of five minor tobacco alkaloids increases nicotine-induced hyperactivity, sensitization and intravenous self-administration in rats. | The international journal of neuropsychopharmacology 20091101 |
| Drugs of abuse that mediate advanced glycation end product formation: a chemical link to disease pathology. | Accounts of chemical research 20090519 |
| Smoking and Parkinson's disease: does nicotine affect alpha-synuclein fibrillation? | Biochimica et biophysica acta 20090201 |
| [Development of analytical method for determination nicotine metabolites in urine]. | Przeglad lekarski 20090101 |
| Meconium nicotine and metabolites by liquid chromatography-tandem mass spectrometry: differentiation of passive and nonexposure and correlation with neonatal outcome measures. | Clinical chemistry 20081201 |
| Nicotine metabolism in pregnant and nonpregnant rabbits. | Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco 20080801 |
| Enantiomeric analysis of anatabine, nornicotine and anabasine in commercial tobacco by multi-dimensional gas chromatography and mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080401 |
| Quantification of nicotine, cotinine, trans-3'-hydroxycotinine, nornicotine and norcotinine in human meconium by liquid chromatography/tandem mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080215 |
| Nornicotine-organocatalyzed aqueous reduction of alpha,beta-unsaturated aldehydes. | Chemical communications (Cambridge, England) 20071214 |
| Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco. | Plant & cell physiology 20071101 |
| Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. | Journal of chromatography. A 20070914 |
| Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract. | Journal of agricultural and food chemistry 20070822 |
| Effects of tobacco and cigarette smoke extracts on serotonergic raphe neurons in the rat. | Neuroreport 20070611 |
| The pharmacological activity of nicotine and nornicotine on nAChRs subtypes: relevance to nicotine dependence and drug discovery. | Journal of neurochemistry 20070401 |
| Expression of the receptor of advanced glycation end products in the gingival tissue of smokers with generalized periodontal disease and after nornicotine induction in primary gingival epithelial cells. | Journal of periodontology 20070401 |
| Nornicotine inhibition of dopamine transporter function in striatum via nicotinic receptor activation. | Synapse (New York, N.Y.) 20070301 |
| Effects of nornicotine enantiomers on intravenous S(-)-nicotine self-administration and cardiovascular function in rats. | Psychopharmacology 20070201 |
| Genetic engineering of Nicotiana tabacum for reduced nornicotine content. | Journal of agricultural and food chemistry 20061129 |
| Re: Receptor for advanced glycation end product (RAGE) upregulation in human gingival fibroblasts incubated with nornicotine. Katz J, Caudle RM, Bhattacharyya I, Stewart CM, Cohen DM (2005;76:1171-1174). | Journal of periodontology 20060201 |
| CYP2A6 AND CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions. | Drug metabolism and disposition: the biological fate of chemicals 20051201 |
| 3-(2-Aminoethyl)pyridine analogs as alpha4beta2 nicotinic cholinergic receptor ligands. | Bioorganic & medicinal chemistry letters 20051001 |
| Nicotine demethylation in Nicotiana cell suspension cultures: N'-formylnornicotine is not involved. | Phytochemistry 20051001 |
| A general procedure for the enantioselective synthesis of the minor tobacco alkaloids nornicotine, anabasine, and anatabine. | The AAPS journal 20050901 |
| Nicotine 5'-oxidation and methyl oxidation by P450 2A enzymes. | Drug metabolism and disposition: the biological fate of chemicals 20050801 |
| Receptor for advanced glycation end product (RAGE) upregulation in human gingival fibroblasts incubated with nornicotine. | Journal of periodontology 20050701 |
| Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis. | The Journal of organic chemistry 20050429 |
| 6'-Methylpyrido[3,4-b]norhomotropane: synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model. | Bioorganic & medicinal chemistry letters 20050215 |
| Nornicotine aqueous aldol reactions: synthetic and theoretical investigations into the origins of catalysis. | The Journal of organic chemistry 20041001 |
| In vitro microsomal [correction of mircosomal] metabolism of N-benzyl and N-benzoylnornicotine derivates by rat. | European journal of drug metabolism and pharmacokinetics 20040101 |
| The nicotinic pharmacophore: thermodynamics of the hydrogen-bonding complexation of nicotine, nornicotine, and models. | The Journal of organic chemistry 20031017 |
| Binding of nicotine and homoazanicotine analogues at neuronal nicotinic acetylcholinergic (nACh) receptors. | Bioorganic & medicinal chemistry letters 20030224 |
| Long-lasting occupancy of central nicotinic acetylcholine receptors after smoking: a PET study in monkeys. | Journal of neurochemistry 20030101 |
| Locomotor stimulant effects of nornicotine: role of dopamine. | Pharmacology, biochemistry, and behavior 20021201 |
| Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. | Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology 20021201 |
| Site of protonation of nicotine and nornicotine in the gas phase: pyridine or pyrrolidine nitrogen? | Journal of the American Chemical Society 20020904 |
| Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. | Clinical chemistry 20020901 |
| Aqueous aldol catalysis by a nicotine metabolite. | Journal of the American Chemical Society 20020403 |
| Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices. | Biochemical pharmacology 20011215 |
| Nornicotine, a nicotine metabolite and tobacco alkaloid: desensitization of nicotinic receptor-stimulated dopamine release from rat striatum. | European journal of pharmacology 20010928 |
| A new and direct synthesis of 2-substituted pyrrolidines. | The Journal of organic chemistry 20010907 |
| In vitro effects of nicotine on mitochondrial respiration and superoxide anion generation. | Brain research 20010504 |
| Accumulation of nicotine and its metabolites in rat brain after intermittent or continuous peripheral administration of [2'-(14)C]nicotine. | Drug metabolism and disposition: the biological fate of chemicals 20010501 |
| Enhancement of haloperidol-induced catalepsy by nicotine: an investigation of possible mechanisms. | Canadian journal of physiology and pharmacology 20001101 |
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