3-[(2S)-1-methylpyrrolidin-2-yl]pyridine

• ChemBase ID: 119383
• Molecular Formular: C10H14N2
• Molecular Mass: 162.23156
• Monoisotopic Mass: 162.11569846
• SMILES: N1([C@H](c2cnccc2)CCC1)C
• Canonical SMILES: CN1CCC[C@H]1c1cccnc1
• 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/t10-/m0/s1
• InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
• IUPAC Traditional name: nicoderm CQ
• Brand Name: Nicorette, Nicotrol
• Synonyms: (-)-Nicotine solution; (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine; (-)-Nicotine; (-)-1-Methyl-2-(3-pyridyl)pyrrolidine; (-)-1-Methyl-2-[3-pyridyl]pyrrolidine; 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine; (-)-Nicotine; Exodus; Nicolan; Niconil; Nicopatch; Nicorette; Nicotell TTS; Nicotin; l-Nicotine; (S)-(-)-Nicotine; (S)-3-(1-methylpyrrolidin-2-yl)pyridine; Nicotine; (-)-尼古丁 溶液; (-)-1-甲基-2-(3-吡啶基)吡咯烷; (-)-尼古丁

Database IDs

• CAS Number: 54-11-5
• EC Number: 200-193-3; 200-835-2
• MDL Number: MFCD00006369
• Beilstein Number: 82109; 5733110
• PubChem SID: 24897663; 162103194; 24897737; 24862741; 24870064
• PubChem CID: 942; 89594
• CHEBI ID: 17688
• ATC CODE: QP53AX13; N07BA01
• CHEMBL: 3
• Chemspider ID: 80863
• DrugBank ID: DB00184
• IUPHAR ligand ID: 2585
• KEGG ID: D03365
• Unique Ingredient Identifier: 6M3C89ZY6R
• Wikipedia Title: Nicotine

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Dichloromethane; ethanol: soluble50 mg/mL; Ether; Ethyl Acetate; Methanol
• Apperance: Colourless to Yellow Oil; yellow liquid
• Melting Point: -79°C (-110.2°F)
• Boiling Point: 243-248 °C; 247°C (476.6°F)
• Flash Point: 101 °C; 2 °C; 213.8 °F; 35.6 °F
• Density: 1.01 g/cm^3; 1.010 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.5265(lit.); n20/D 1.528
• Optical Rotation: [α]20/D -166°, neat; [α]20/D -168±5°, c = 1% in acetone; [α]20/D -169°(lit.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: QS5250000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Highly toxic (T+); Harmful (Xn)
• UN Number: 1648; 1654; 1992
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 23/24/25-39/23/24/25; 25-27-51/53
• Safety Statements: 16-36/37; 36/37-45; 36/37-45-61
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302 + H312 + H332-H319; H301-H310-H411; H301-H311-H331-H370
• GHS Precautionary statements: P210-P280-P305 + P351 + P338; P260-P280-P301 + P310-P311; 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 1648 3/PG 2; UN 1654 6.1/PG 2; UN 1992 3/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: smoked (as smoking tobacco, mapacho, etc.), insufflated (as tobacco snuff or nicotine nasal spray), chewed (as nicotine gum, tobacco gum or chewing tobacco), transdermal (as nicotine patch, nicogel or topical tobacco paste), intrabuccal (as dipping tobacco, snuffs, dissolvable tobacco or creamy snuff), vaporized (as electronic cigarette, etc.), directly inhaled (as nicotine inhaler), oral (as nicotini), buccal (as snus)
• Bioavailability: 20 to 45% (oral)
• Dependency Liability: Moderate
• Half Life: 2 hours; 20 hours active metabolite (cotinine)
• Metabolism: hepatic
• Legal Status: GSL (UK); OTC (US); Unscheduled (Australia)
• Pregnancy Category: D (US)
• Gene Information: human ... CHRNA2(1135); human ... CHRNA2(1135), CHRNA3(1136), CHRNB2(1141), CHRNB4(1143), CYP2A6(1548), KCNH1(3756)mouse ... Chrna7(11441), Chrnb1(11443)rat ... Chrna1(79557), Chrna2(170945), Chrna4(25590), Chrna7(25302), Chrnb2(54239), Chrnb4(25103); human ... CHRNA3(1136), CHRNB2(1141), CHRNB4(1143), CYP2A6(1548), KCNH1(3756)mouse ... Chrna7(11441), Chrnb1(11443)rat ... Chrna1(79557), Chrna2(170945), Chrna4(25590), Chrna7(25302), Chrnb2(54239), Chrnb4(25103)

Product Information

• Purity: ≥99% (GC); ≥99.0% (sum of enantiomers, GC); 95+%; 98%
• Concentration: 1.0 mg/mL; 1.0 mg/mL±5% in methanol; 100 ng/μL in acetonitrile
• Grade: analytical standard, for drug analysis; PESTANAL®, analytical standard
• Impurities: ~1% water
• Empirical Formula (Hill Notation): C10H14N2
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - N3876

Frequently Asked Questions
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Biochem/physiol Actions
原型烟酸乙酰胆碱受体激动剂;天然异构体。

Sigma Aldrich - 186376

Biochem/physiol Actions
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Sigma Aldrich - 72290

Biochem/physiol Actions
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.
Caution
may discolor to brown on storage

Sigma Aldrich - 36733

Biochem/physiol Actions
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 46343

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - N412450

(S)-(-)-Nicotine is a prototype nicotinic acetylcholine receptor agonist. (S)-(-)-Nicotine is the naturally occurring isomer. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of sm

REFERENCES

• Geffken, D., et al.: Am. J. Epidemiol., 153, 242 (2001)
• Bolego, C., et al.: Cardiovasc. Res., 53, 568 (2001)
• Leone, A., et al.: Curr. Pharm. Des., 1, 2199 (2001)