(−)-nicotine

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

Nicotine is an alkaloid found primarily in plants of the nightshade family, notably in tobacco; it is also synthesized. Nicotine is used recreationally for its stimulant and anxiolytic effects. In tobacco leaves, nicotine constitutes about 0.6–3.0% of the dry weight, and smaller, trace quantities occur in other Solanaceae crops such as tomatoes, potatoes, and eggplants. In pure form, nicotine is a colorless to yellowish, oily liquid that readily penetrates biological membranes and acts as a potent neurotoxin in insects, where it serves as an antiherbivore toxin. Historically, it was widely use

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

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

~51 min read

Encyclopedic overview

52 sections

Contents

Uses
Medical
Pesticide
Performance
Recreational
Contraindications
Adverse effects
Sleep
Cardiovascular system
Blood pressure
Reinforcement disorders
Cancer
Genotoxicity
Pregnancy and breastfeeding
Overdose
Toxicity
Drug interactions
Pharmacodynamic
Pharmacokinetic
Pharmacology
Pharmacodynamics
Central nervous system
Acute effects on CNS
Long-term effects on CNS
Sympathetic nervous system
Adrenal medulla
Pharmacokinetics
Influence of ionization state
Metabolism
Chemistry
Stereochemistry
Preparation
Biosynthesis
Detection in body fluids
Methods for analysis of enantiomers
Analogues and derivatives
Natural analogues
Synthetic analogues
Natural occurrence
History
Society and culture
Regulation
Age limits on purchase
In media
Research
Central nervous system
Immune system
Optopharmacology
Oral health
See also
References
External links

In humans, nicotine acts primarily as a stimulant by binding to and activating nicotinic acetylcholine receptors (nAChRs) in the central nervous system and peripheral tissues. This results in the release of neurotransmitters such as dopamine, acetylcholine, and norepinephrine, producing effects including increased alertness, reduced anxiety, and mild euphoria. Nicotine is typically consumed through tobacco smoking, vaping, or other nicotine delivery systems. An average cigarette yields about 2 mg of absorbed nicotine, a dose sufficient to produce reinforcement and dependence while remaining far below toxic levels.

Excerpted from Wikipedia’s “(−)-nicotine” article, available under the CC BY-SA 4.0 licence.