(−)-Nicotin

Also known as nicotine, 3-(N-methylpyrollidino)pyridine, Nicotine betadex, Nicotine polacrilex, Nicotine, (S)-3-(1-methylpyrrolidin-2-yl)pyridine, (S)-Nicotine, (S)-(−)-nicotine

chemische Verbindung

OverviewAI-generated

(−)-Nicotine is a chemical compound with the formula C₁₀H₁₄N₂ and a mass of 162.115698448. Its IUPAC name is 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine. The substance has a density of 1.01 and an ionization energy of 8.01. It exhibits a melting point range of -110 to -79 and a decomposition point of 482. The flash point is recorded at 203, with a vapor pressure of 0.08.

Flammability limits for the compound range from a lower limit of 0.7 to an upper limit of 4. The time-weighted average exposure limit is 0.5, and the immediately dangerous to life or health value is 5. It has zero hydrogen bond donors and two hydrogen bond acceptors. The compound is referenced by 2,926 other encyclopedia articles. Scientific literature includes 68,056 PubMed entries associated with the query for (−)-nicotine.

Synthesized by Vinony from 30 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.imageL: Nicotine molecule ball from xtal.png
Drug.image_classL: bg-transparent
Drug.imageR: Nicotine molecule spacefill from xtal.png
Drug.image_classR: bg-transparent
Drug.tradename: Nicorette, others
Drug.pregnancy_AU: D
Drug.pregnancy_US: D
Drug.legal_AU: S7
Drug.legal_CA: Unscheduled
Drug.legal_BR: Unscheduled
Drug.legal_DE: Unscheduled
Drug.legal_NZ: Unscheduled
Drug.legal_UK: GSL
Drug.legal_US: OTC
Drug.legal_US_comment: and prescription
Drug.legal_UN: Unscheduled
Drug.legal_EU: Unscheduled / OTC
Drug.legal_status: SE: Unscheduled / OTC

via Wikipedia infobox

Chemical data

Formula: C10H14N2
Molecular weight: 162.23 g/mol
IUPAC name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
SMILES: CN1CCC[C@H]1C2=CN=CC=C2
InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N
XLogP: 1.2
Polar surface area: 16.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1984
Admin. routes: oral, topical
Indications: nicotine dependence, smoking cessation, memory impairment, post operative nausea and vomiting

via ChEMBL · EBI

Research

68,056 papers

Nicotine: From Discovery to Biological Effects.ReviewInternational journal of molecular sciences · 2023Sansone L, Milani F, Fabrizi R et al.DOI: 10.3390/ijms241914570
Nicotine's effect on cognition, a friend or foe?ReviewProgress in neuro-psychopharmacology & biological psychiatry · 2023Wang Q, Du W, Wang H et al.DOI: 10.1016/j.pnpbp.2023.110723
Cognitive Effects of Nicotine: Recent Progress.ReviewCurrent neuropharmacology · 2018Valentine G, Sofuoglu MDOI: 10.2174/1570159X15666171103152136
Nicotinic acetylcholine receptors and nicotine addiction: A brief introduction.ReviewNeuropharmacology · 2020Wittenberg RE, Wolfman SL, De Biasi M et al.DOI: 10.1016/j.neuropharm.2020.108256
E-cigarettes, nicotine, the lung and the brain: multi-level cascading pathophysiology.ReviewThe Journal of physiology · 2020Herman M, Tarran RDOI: 10.1113/JP278388
Anhedonia in Nicotine Dependence.ReviewCurrent topics in behavioral neurosciences · 2022Gilbert DG, Stone BMDOI: 10.1007/7854_2022_320
Nicotine forms: why and how do they matter in nicotine delivery from electronic cigarettes?ReviewExpert opinion on drug delivery · 2020Gholap VV, Kosmider L, Golshahi L et al.DOI: 10.1080/17425247.2020.1814736
Nicotine is an Immunosuppressant: Implications for Women's Health and Disease.ReviewJournal of neuroimmunology · 2024White AM, Craig AJ, Richie DL et al.DOI: 10.1016/j.jneuroim.2024.578468

via PubMed

Wikidata facts

Named after: Jean Nicot
Mass: 162.115698448
Has use: medication

Show 23 more facts

found in taxon: Erythroxylum macrophyllum
chemical formula: C₁₀H₁₄N₂
isomeric SMILES: CN1CCC[C@H]1C2=CC=CN=C2
NCI Thesaurus ID: C691
active ingredient in: tobacco product
has effect: nicotine poisoning
ionization energy: 8.01
density: 1.01
melting point: -79
decomposition point: 482
vapor pressure: 0.08
flash point: 203
immediately dangerous to life or health: 5
lower flammable limit: 0.7
upper flammable limit: 4
time-weighted average exposure limit: 0.5
NIOSH Pocket Guide ID: 0446
different from: nicotinic acid
on focus list of Wikimedia project: Wikipedia:Vital articles/Level/4
medical condition treated: nicotine dependence
canonical SMILES: N=1C=CC=C(C1)C2N(C)CCC2
Commons category: Nicotine
legal status (medicine): boxed warning

Sources (8)

via Wikidata · CC0

Article · Deutsch

Nicotin, auch Nikotin, ist ein natürlich in den Blättern der Tabakpflanze sowie in geringerer Konzentration auch in anderen Nachtschattengewächsen vorkommendes Alkaloid, das erregende oder lähmende Wirkungen auf Ganglien des vegetativen Nervensystem hat. Selten werden Nicotinderivate als Nicotinoide bezeichnet; meist sind damit die synthetischen, als Insektizide eingesetzten Neonicotinoide gemeint. Nicotin ist als psychoaktiver Wirkstoff bzw. Rauschgift von z. B. Zigaretten eine weit verbreitete Volksdroge (siehe Rauchen).

Abstract from DBpedia / Wikipedia · CC BY-SA