Compound: nicotine
SMILES: n1cc(ccc1)[C@H]2N(CCC2)C
InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N
Synonyms: nicotine, L-Nicotine, 54-11-5, (-)-Nicotine, (S)-Nicotine, (S)-3-(1-methylpyrrolidin-2-yl)pyridine, (S)-(-)-Nicotine, Habitrol, Nicotrol, 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine, Nicoderm, Nicoderm Cq, Fumetobac, Nicocide, Prostep, Tendust, Nico-dust, Nicotine alkaloid, Emo-nik, Nico-Fume, Mach-Nic, Nic-Sal, 1-Methyl-2-(3-pyridyl)pyrrolidine, Flux MAAG, Nicotina, Nikotyna, Ortho N-4 dust, Ortho N-5 dust, XL All Insecticide, Niagara P.A. dust, Destruxol orchid spray, L(-)-nicotine, Black Leaf 40, 3-(N-Methylpyrollidino)pyridine, 3-(N-Methylpyrrolidino)pyridine, Nicabate, Niquitin, Tabazur, L-3-(1-Methyl-2-pyrrolidyl)pyridine, Ortho N-4 and N-5 dusts, Nicotin, (-)-3-(1-Methyl-2-pyrrolidyl)pyridine, Black leaf, beta-Pyridyl-alpha-N-methylpyrrolidine, RCRA waste number P075, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine, Nikotin, ENT 3,424, 3-(2-(N-methylpyrrolidinyl))pyridine, Nicotinum, 3-((2S)-1-methylpyrrolidin-2-yl)pyridine, Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)-, 6M3C89ZY6R, Pyrrolidine, 1-methyl-2-(3-pyridal)-, DTXSID1020930, CHEBI:17688, (S)-3-(N-methylpyrrolidin-2-yl)pyridine, Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-, DTXCID50930, CHEBI:18723, NSC-5065, Pyridine, 3-[(2S)-1-methyl-2-pyrrolidinyl]-, blip, Nicorelief, Nicopass, Nicopatch, Stoppers, bjwc nicotine, euqate nicotine, Stubit, nictoine gum, Lucy nicotine, Niquitin mint, Equate Nicotine, Leader Nicotine, NicFix, Nicorette Mint, Niquitin clr, quitine nicotine, Rexall Nicotine, Maxi Nicotine, Mini Nicotine, Nicorette invisi, Nicotine Mini, Nicotinum,, Careone Nicotine, Good Sense, Habitrol Lozenge, Sunmark Nicotine, Topcare Nicotine, NicFix Plus, HEB Nicotine, Nicotine polarilex, Nicotinell classic, Nicotinell support, Habitrol Step 1, Habitrol Step 2, Habitrol Step 3, Niquitin pre-quit, Stop Smoking Aid, Nicorette Original, Care One Nicotine, Nicoitne Polacrilex, DG Health nicotine, Nicotine transdermal, Niquitin minis mint, 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Polacrilex, Berkley and Jensen Nicotine, up and up uncoated nicotine, Nicotine Polacrilex Original, Nicotine Coated Fruit Flavor, Nicorette 4mg Cinnamon Surge, up and up mint mini nicotine, up and up nicotine mini mint, Nicotine Polacrilex, Original, up and up cherry ice nicotine, Up and Up Nicotine Polacrilex, NICOTINE POLACRILEX MINI, up and up citrus mini nicotine, Good Neighbor Pharmacy Nicotine, Health Mart Nicotine Polacrilex, Nicotine Polacrilex Coated Mint, Careone Mini Nicotine Polacrilex, Habitrol Lozenge Original Flavor, Nicotine Polacrilex Coated Fruit, Nicotine Polacrilex Lozenge Mint, up and up uncoated mint nicotine, Nicotine Polacrilex Lozenge 2 mg, Nicotine Polacrilex Lozenge 4 mg, Nicotine Transdermal System Patch, up and up coated cinnamon nicotine, up and up mini nicotine polacrilex, Nicotine Polacrilex coated cinnamon, Nicotine Polacrilex Origianl Flavor, Nicotine Polacrilex Original Flavor, Nicotine Transdermal System Step 1, Nicotine Transdermal System Step 2, Nicotine Transdermal System Step 3, good neighbor pharmacy nicotine mini, Nicotine Polacrilex Coated Ice Mint, NiEnjoy Nicotine Transdermal System, up and up coated cool mint nicotine, up and up uncoated original nicotine, up and up coated mint freeze nicotine, Berkley and Jensen Nicotine Polacrilex, UP AND UP COATED FRUIT NICOTINE, Clear Nicotine Transdermal System Patch, Nicorette White Mint nicotine polacrilex, LEADER NICOTINE TRANSDERMAL SYSTEM, Nicorette Fruit Chill nicotine polacrilex, Habitrol Nicotine Polacrilex Lozenge Mint, NiEnjoy Nicotine Transdermal System Patch, Leader Nicotine Transdermal System Step 1, Leader Nicotine Transdermal System Step 2, Leader Nicotine Transdermal System Step 3, Sielkin QUIT SMOKING NICOTINE PATCHES, Rugby Nicotine Polacrilex Gum, Mint Flavor, AMAZON BASIC CARE NICOTINE POLACRILEX, SEFUDUN QUIT SMOKING NICOTINE PATCHES, Nicorette 4mg Fruit Chill Gum, Lil Drug Store, Rugby Nicotine Polacrilex Gum, Original Flavor, Sielkin QUIT SMOKING NICOTINE PATCHES 14mg, Sielkin QUIT SMOKING NICOTINE PATCHES 21mg, Nicorette 4mg White Ice Mint Gum, Lil Drug Store, Rugby Nicotine Polacrilex Gum, Coated Mint Flavor, Rugby Nicotine Polacrilex Gum, Coated Fruit Flavor, 200-193-3, 686-240-2, 3-(1-Methyl-2-pyrrolidinyl)pyridine, NSC5065, Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, MFCD00006369, NSC 5065, beta-Pyridyl-alpha-N-methyl pyrrolidine, 3-(1-Methyl-2-pyrollidinyl)pyridine, (-)-3-(N-Methylpyrrolidino)pyridine, Micotine, 1-Methyl-2-(3-pyridiyl)pyrrolidine, Nikotin [German], S-(-)-Nicotine, Nikotyna [Polish], Nicotina [Italian], Pyrrolidine, 1-methyl-2-(3-pyridyl)-, Nicotrol Inhaler, Nicotrol NS, Nicotine [for single use], NICOTINE-L (BASE), destruxol, fumeto bac, Caswell No. 597, Nicotine [BSI:ISO], 104062-50-2, Nicotine-D salicylate, CAS-54-11-5, DL-tetrahydronicotyrine, Habitrol (TN), Nicotine (USP), Nicotine [ISO], SMR000059074, CCRIS 1637, HSDB 1107, (S)-(-)-Nicotine (1.0 mg/mL in Methanol), Nicotine [USP:BAN], EINECS 200-193-3, methyl-2-pyrrolidinyl)pyridine, UN1654, RCRA waste no. P075, EPA Pesticide Chemical Code 056702, UNII-6M3C89ZY6R, delta-Nicotine, AI3-03424, Nicotine betadex, 1-methyl-2-(3-pyridal)-pyrrolidene, nicotine s(-), a-N-methylpyrrolidine, Campbell's nico-soap, 3-N-methylpyrrolidine, R)-(+)-nicotine, a -N-methylpyrrolidine, CHEMBL3, 1uw6, NICOTINE [HSDB], NICOTINE (TPD), alpha-N-methylpyrrolidine, NICOTINE [MI], Nicotine [UN1654], NICOTINE [VANDF], NICOTINUM [HPUS], (S)-(-)--nicotine, NICOTINE [MART.], (-)-1-Methyl-2-(3-pyridyl)pyrrolidine, bmse000105, Epitope ID:226549, NICOTINE [WHO-DD], (2S) 3-(1-Methyl-pyrrolidin-2-yl)-pyridine, EC 200-193-3, Nicotine polacrilex [USAN], Epitope ID:1597626, S-()-Nicotine-pyridine-d4, SCHEMBL20192, MLS001055457, MLS001335905, BIDD:GT0599, NICOTINE [ORANGE BOOK], GTPL2585, SCHEMBL6810286, SCHEMBL7957968, NICOTINE [EP MONOGRAPH], NICOTINE [USP MONOGRAPH], SCHEMBL11568397, SCHEMBL29350932, BDBM82070, l-Nicotine, 1mg/ml in Methanol, l-Nicotine, 10mg/ml in Methanol, l-Nicotine, 50mg/ml in Methanol, HMS2230H17, HMS3259E16, Nicotine [UN1654]  [Poison], HY-B0638, l-Nicotine, 100mg/ml in Methanol, MSK20302, Nicotine 10 microg/mL in Methanol, Tox21_201814, Tox21_300174, EBC-12757, Nicotine 100 microg/mL in Methanol, PDSP1_000113, PDSP1_000465, PDSP2_000463, PDSP2_000555, SBB012359, 1-methyl-2-(3-pyridal)-Pyrrolidine, AKOS016843798, Nicotine 1000 microg/mL in Methanol, 3-(1-methyl-2-pyrrolidinyl)-Pyridine, CCG-204892, CS-3999, DB00184, NC00577, SB12751, SDCCGMLS-0066911.P001, SDCCGSBI-0050785.P004, NCGC00090693-01, NCGC00090693-02, NCGC00090693-03, NCGC00090693-04, NCGC00090693-05, NCGC00090693-06, NCGC00090693-07, NCGC00090693-08, NCGC00090693-09, NCGC00254095-01, NCGC00259363-01, (-)-Nicotine, >=99% (GC), liquid, ST069320, 3-[(S)-1-Methylpyrrolidin-2-yl]pyridine, SBI-0050785.P003, CAS_29790-52-1, N0079, NS00010445, C00745, D03365, EN300-304948, P10017, (-)-.beta.-Pyridyl-.alpha.-N-methylpyrrolidine, AB00694322_12, (-)-Nicotine, PESTANAL(R), analytical standard, 3-((2S)-1-METHYL-2-PYRROLIDINYL)PYRIDINE, SR-05000001762-5, BRD-K05395900-322-02-1, BRD-K05395900-322-04-7, BRD-K05395900-322-05-4, Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl), (S)-, Q28086552, Z1198150037, 434F7990-3240-4A43-ACEC-E6CC1E495FA0, (S)-(-)-NICOTINE; 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE
Theoretical properties:
molecular_formula: C10H14N2
molecular_weight: 162.23 g/mol
exact_mass: 162.115698455 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 12
topological_polar_surface_area: 16.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless to pale yellow, oily liquid
color: Colorless to pale yellow, oily liquid
odor: Fish-like odor when warm
boiling_point: 476.1 °F at 745 mmHg (EPA, 1998)
melting_point: -110 °F (EPA, 1998)
density: 1.0097 at 68 °F (EPA, 1998) - Denser than water; will sink
solubility: Miscible (NTP, 1992)
flash_point: 203 °F (NIOSH, 2024)
vapor_pressure: 1 mmHg at 143.24 °F (EPA, 1998)
Descriptions:
{"pubchem": "Nicotine can cause developmental toxicity according to state or federal government labeling requirements.", "chebi": "A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has <i>S</i>-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from <em>Nicotiana tabacum</em>.", "chembl": "NICOTINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "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\u20133.0% 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 used as an insecticide, and its structure provided the basis for synthetic neonicotinoid pesticides.\nIn 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.\nNicotine is highly addictive, and nicotine dependence is characterized by tolerance, physical dependence, psychological dependence, and nicotine withdrawal symptoms such as irritability, anxiety, and difficulty concentrating. Nicotine replacement therapy (NRT) products, including gums, patches, and lozenges, deliver the compound in slower, lower doses that are less addictive and are used medically to help people quit smoking. Synthetic derivatives of nicotine, such as varenicline, act as partial agonists at nicotinic receptors and are also used as smoking cessation aids.\nNicotine itself is not classified as a carcinogen by either the International Agency for Research on Cancer or the Surgeon General of the United States. At high doses it can cause nicotine poisoning and respiratory paralysis. Chronic exposure may also affect the immune, cardiovascular, and nervous systems. Nicotine is also a known teratogen, associated with adverse developmental effects during pregnancy, and may impair adolescent neurodevelopment, though the extent of this effect in humans remains debated.\n\n"}