Nicotine

Nicotine
Compound Structure:
Synonyms: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine; nicotine; L-Nicotine; (-)-Nicotine; (S)-Nicotine; Habitrol; Nicotrol; (S)-(-)-Nicotine; Nicoderm; Fumetobac; Micotine; Nicocide; Nico-dust; Nicotine alkaloid; Emo-nik; Nicotina; Nikotyna; L(-)-nicotine
Compound ID: NMPC-1311
PubChem ID:

89594

Molecular Formula: C10H14N2
Canonical SMILES: CN1CCCC1C2=CN=CC=C2
InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N
About the compound:

Nicotine is a colorless to light yellow or brown liquid that is combustible and toxic if inhaled or absorbed through the skin. When burned, it produces toxic oxides of nitrogen. The naturally occurring and most active enantiomer of nicotine, known as (S)-nicotine, is isolated from the tobacco plant, Nicotianatabacum. It functions as a phytogenic insecticide, a teratogenic agent, a neurotoxin, an anxiolytic drug, and a nicotinic acetylcholine receptor agonist, among other roles. It is the conjugate base of (S)-nicotinium(1+) and is an enantiomer of (R)-nicotine. Nicotine is a highly toxic alkaloid and a well-known agonist at nicotinic cholinergic receptors. It stimulates neurons dramatically and eventually blocks synaptic transmission, making it an important substance both medically and recreationally due to its presence in tobacco smoke.This compound is naturally produced in the nightshade family of plants, predominantly found in tobacco and Duboisiahopwoodii. It is widely used as a recreational stimulant and anxiolytic. Medically, it is employed in smoking cessation therapies to alleviate withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors, except at two nicotinic receptor subunits where it functions as an antagonist. Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco and is also present in minute concentrations in other Solanaceae family plants, including potatoes, tomatoes, and eggplants. Its primary function in plants is as an antiherbivore toxin. Historically, nicotine was widely used as an insecticide, and neonicotinoids, which are structurally similar to nicotine, continue to be extensively used. Nicotine is known for its high addiction potential. Slow-release forms such as gums and patches are less addictive and assist in smoking cessation. Research suggests that monoamine oxidase inhibitors in tobacco smoke may enhance nicotine's addictive properties. The lower dose limit for fatal outcomes in adults is estimated to be 500–1,000 mg of ingested nicotine. Nicotine addiction involves various aspects, including drug-reinforced behavior, compulsive use, tolerance, sensitization, and physical and psychological dependence. Nicotine is considered safe when used as a tool for quitting smoking. It may have adverse effects on cognitive development in adolescence, but these findings' relevance to human development is disputed. At low doses, nicotine has a mild analgesic effect. While it is not generally considered a carcinogen, it is recognized as a teratogen and can produce birth defects in humans. The median lethal dose of nicotine in humans is unknown. Nicotine is used medically in smoking cessation therapies and is being researched for potential benefits in treating Parkinson's disease, dementia, ADHD, depression, and sarcoma. Recreational use of nicotine is widespread and highly addictive. Nicotine-containing products are sometimes used for their performance-enhancing effects on cognition. Despite its potential benefits, nicotine is addictive and can lead to dependence rapidly. Recreational nicotine products include chewing tobacco, cigars, cigarettes, e-cigarettes, snuff, pipe tobacco, snus, and nicotine pouches.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

162.23 g/mol

XLogP3

1.2

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

1

Exact Mass

162.115698455 g/mol

Monoisotopic Mass

162.115698455 g/mol

Topological Polar Surface Area

16.1Ų

Heavy Atom Count

12

Formal Charge

0

Complexity

147

Isotope Atom Count

0

Defined Atom Stereocenter Count

1

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Nicotine appears as a colorless to light yellow or brown liquid. Combustible. Toxic by inhalation and by skin absorption. Produces toxic oxides of nitrogen during combustion.

Boiling Point

247°C

Melting Point

-79°C

Density

1.01

Solubility 

Miscible with water below 60 °C; very sol in alcohol, chloroform, ether, petroleum ether, kerosene, oils

Vapor Pressure

0.08 [mmHg]

Source: PubChem            

Source Species: Nicotiana tabacum
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