3-(1-methylpyrrolidin-2-yl)pyridine

• ChemBase ID: 69
• Molecular Formular: C10H14N2
• Molecular Mass: 162.23156
• Monoisotopic Mass: 162.11569846
• SMILES: N1(C(CCC1)c1cccnc1)C
• Canonical SMILES: CN1CCCC1c1cccnc1
• InChI: 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
• InChIKey: SNICXCGAKADSCV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1-methylpyrrolidin-2-yl)pyridine
• IUPAC Traditional name: nicotine
• Brand Name: Black Leaf; Black Leaf 40; Campbell's Nico-Soap; Commit; Destruxol Orchid Spray; Emo-Nik; Flux Maag; Fumetobac; Habitrol; Mach-Nic; Niagara P.A. Dust; Nic-Sal; Nico-Dust; Nico-Fume; Nicocide; Nicoderm; Nicoderm Cq; Nicorette; Nicorette Plus; Nicotin; Nicotina; Nicotine Polacrilex; Nicotrol; Nicotrol Inhaler; Nicotrol Ns; Nikotin; Nikotyna; Ortho N-4 Dust; Ortho N-5 Dust; Prostep; Tendust
• Synonyms: (±)-Nicotine; 3-(1-Methyl-2-pyrrolidinyl)pyridine; (±)-Nicotine; (±)-3-(1-Methyl-2-pyrrolidinyl)pyridine; (R,S)-Nicotine; 1-Methyl-2-(3-pyridyl)pyrrolidine; DL-Nicotine; rac-Nicotine; 3-(1-methylpyrrolidin-2-yl)pyridine; L-Nicotine; Nicotine Alkaloid; Nicotine; L-1-Methyl-2-[3-pyridyl]pyrrolidine; (-)-NICOTINE FREE BASE

Database IDs

• CAS Number: 54-11-5; 22083-74-5
• EC Number: 200-193-3
• MDL Number: MFCD00065370
• Beilstein Number: 82108
• PubChem SID: 46506924; 160963532; 24897418
• PubChem CID: 942

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.9628259
• LogD (pH = 7.4): -0.31012845
• Log P: 1.1625347
• Molar Refractivity: 49.655 cm^3
• Polarizability: 19.449343 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.87
• LOG S: -0.24
• Solubility (Water): 9.33e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 g/mL; Chloroform; Ethanol; ethanol: soluble50 mg/mL; Methanol
• Apperance: Clear Colourless to Light Yellow Oil; yellow liquid
• Melting Point: -79 °C
• Boiling Point: 247 °C at 745 mmHg (partial decomposition); 67°C/0.5 mm
• Flash Point: 101 °C; 101°C; 213.8 °F; 214 °F
• Auto Ignition Point: 244 °C (471 °F)
• Density: 1.0097 at 20 °C (water = 1); 1.02 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0425 mm Hg at 20 °C
• Vapor Density: 5.6 (air = 1)
• Optical Rotation: [α]25/D 0°(lit.)
• Hydrophobicity(logP): 0.883; 1.1

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate, Store Under Nitrogen, Protect from light
• RTECS: QS5250000; QS5257500
• European Hazard Symbols: Nature polluting (N); Highly toxic (T+)
• UN Number: 1654
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 25-27-51/53; R:25-27-51/53
• Safety Statements: 36/37-45-61; S:45-61-36/37
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H411
• GHS Precautionary statements: P273-P280-P301 + P310-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1654 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... CHRNA2(1135), CHRNA3(1136), CHRNA4(1137)rat ... Chrna3(25101), Chrna4(25590), Chrna7(25302)

Product Information

• Purity: ≥99% (TLC); ≥99.0% (TLC); 95%; 98-100%
• Empirical Formula (Hill Notation): C10H14N2

DETAILS

MP Biomedicals - 02190671

Free Base
Purity: 98-100% (~ 6.22M)
Clear light yellow liquid

DrugBank - DB00184

• Drug Groups: approved
• Description: Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. [PubChem]
• Indication: For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.
• Pharmacology: Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.
• Toxicity: Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD₅₀= 24 mg/kg (orally in mice).
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, cotinine is the primary metabolite.
• Absorption: Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.
• Half Life: Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours
• Protein Binding: Less than 5%
• Elimination: About 10% of the nicotine absorbed is excreted unchanged in the urine.
• Distribution: * 2 to 3 L/kg
• Clearance: * 1.2 L/min [healthy adult smoker]
• References: Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [Pubmed] ; de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [Pubmed] ; de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [Pubmed] ; Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - N0267

Biochem/physiol Actions
Prototype nicotinic acetylcholine receptor agonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. N0267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - N412420

Nicotine is an alkaloid isolated from plants. Nicotine is an active stimulant, having both addictive and carcinogenic properties. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment o

REFERENCES

• Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. Pubmed
• de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. Pubmed
• de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. Pubmed
• Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. Pubmed
• Ferretti, G., et al.: J. Med. Chem., 45, 4724 (2002)
• Guillen, M., et al.: J. Agric. Food Chem., 53, 1093 (2002)
• Ramunno, A., et al.: Bioorg. Med. Chem. Lett., 15, 3237 (2002)
• Alburges, M., et al.: Eur. J. Pharmacol., 573, 124 (2002)