Nicotine
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Basic Info
| Common Name | Nicotine(F06032) |
| 2D Structure | |
| FRCD ID | F06032 |
| CAS Number | 54-11-5 |
| PubChem CID | 89594 |
| Formula | C10H14N2 |
| IUPAC Name | 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine |
| InChI Key | SNICXCGAKADSCV-JTQLQIEISA-N |
| 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 |
| Canonical SMILES | CN1CCCC1C2=CN=CC=C2 |
| Isomeric SMILES | CN1CCC[C@H]1C2=CN=CC=C2 |
| Synonyms |
nicotine
L-Nicotine
54-11-5
(-)-Nicotine
(S)-Nicotine
Habitrol
(S)-3-(1-methylpyrrolidin-2-yl)pyridine
Nicoderm
Nicotrol
(S)-(-)-Nicotine
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Pyridines and derivatives |
| Subclass | Pyrrolidinylpyridines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Pyrrolidinylpyridines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Pyrrolidinylpyridine - Alkaloid or derivatives - Aralkylamine - N-alkylpyrrolidine - Heteroaromatic compound - Pyrrolidine - Tertiary aliphatic amine - Tertiary amine - Azacycle - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic heteromonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 162.236 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 147 |
| Monoisotopic Mass | 162.116 |
| Exact Mass | 162.116 |
| XLogP | 1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9748 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8867 |
| P-glycoprotein Substrate | Substrate | 0.5000 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8998 |
| Non-inhibitor | 0.9368 | |
| Renal Organic Cation Transporter | Inhibitor | 0.6868 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4196 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7998 |
| CYP450 2D6 Substrate | Substrate | 0.8918 |
| CYP450 3A4 Substrate | Non-substrate | 0.5000 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6347 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8433 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8838 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8543 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8308 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7589 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8851 |
| Non-inhibitor | 0.7978 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9626 |
| Fish Toxicity | High FHMT | 0.7423 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5917 |
| Honey Bee Toxicity | Low HBT | 0.8593 |
| Biodegradation | Not ready biodegradable | 0.9478 |
| Acute Oral Toxicity | II | 0.7410 |
| Carcinogenicity (Three-class) | Non-required | 0.7042 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.7273 | LogS |
| Caco-2 Permeability | 1.2662 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.4798 | LD50, mol/kg |
| Fish Toxicity | 1.2653 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3274 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Thyme (Creeping thyme, Cretan oregano/Turkish oregano, Lemon savory, Lemon thyme/citrus thyme, Marjoram, Mastic thyme, Oregano, Summer savory, Syrian oregano/bible hyssop/za'atar, Winter savory,) | 0256070 | European Union | 0.4 | 04/01/2018 | |
| Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L... | 0256080 | European Union | 0.4 | 04/01/2018 | |
| Pear | Japan | 2ppm | |||
| Allspice/pimento | 0820010 | European Union | 0.3 | 04/01/2018 | |
| Rose hips | 0154050 | European Union | 0.3 | 04/01/2018 | |
| (f) herbs and edible flowers | 0256000 | European Union | 0.4 | 04/01/2018 | |
| Chervil | 0256010 | European Union | 0.4 | 04/01/2018 | |
| Chives (Chinese chives/oriental garlic/garlic chives, Ramson/wild garlic/bear's garlic,) | 0256020 | European Union | 0.4 | 04/01/2018 | |
| Parsley (Root parsley leaves,) | 0256040 | European Union | 0.4 | 04/01/2018 | |
| Sage (Borage, Curry herb, Greek sage, Jamé's sage/Mexican sage, Other species and hybrids of genus Salvia, not elsewhere mentioned,) | 0256050 | European Union | 0.4 | 04/01/2018 | |
| Rosemary (Santolina/green lavander cotton, Green santolina,) | 0256060 | European Union | 0.4 | 04/01/2018 | |
| Fruit spices | 0820000 | European Union | 0.3 | 04/01/2018 | |
| Laurel/bay leaves (Curry leaves, Kaffir lime leaves, Siamese cassia, Wild betel leaves, Pandan leaves,) | 0256090 | European Union | 0.4 | 04/01/2018 | |
| Tarragon (Aztec sweet herb, Epazote/Mexican tea/wormseed, Hyssop, Lemongrass, Mexican oregano, Nettle, Other species of the genus Urtica, not elsewhere mentioned, Russian tarragon, Stevia,) | 0256100 | European Union | 0.4 | 04/01/2018 | |
| Others (2) | 0256990 | European Union | 0.4 | 04/01/2018 | |
| Wild fungi (Ceps/porcino mushrooms, Chanterelles, Hedgehog mushrooms, Horns of plenty/black trumpets, Morels, Périgord black truffles, Piemont white truffles, Saint George's mushrooms, Scotch bonne... | 0280020 | European Union | 0.04 | 04/01/2018 | |
| Teas | 0610000 | European Union | 0.6 | 04/01/2018 | |
| Herbal infusions from | 0630000 | European Union | 0.5 | 04/01/2018 | |
| (a) flowers | 0631000 | European Union | 0.5 | 04/01/2018 | |
| Chamomile | 0631010 | European Union | 0.5 | 04/01/2018 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Consortium on Methods Evaluating Tobacco: Research Tools to Inform US Food and Drug Administration Regulation of Snus. | Nicotine Tob Res | 2018 Sep 25 | 29059363 |
| Effect of e-liquid flavor on electronic cigarette topography and consumptionbehavior in a 2-week natural environment switching study. | PLoS One | 2018 May 2 | 29718974 |
| Mechanisms of toxicity and biomarkers of flavoring and flavor enhancing chemicalsin emerging tobacco and non-tobacco products. | Toxicol Lett | 2018 May 15 | 29481849 |
| Preclinical evidence for combining the 5-HT2C receptor agonist lorcaserin andvarenicline as a treatment for nicotine dependence. | Addict Biol | 2018 Mar 2 | 29498158 |
| A systematic review of consumer preference for e-cigarette attributes: Flavor,nicotine strength, and type. | PLoS One | 2018 Mar 15 | 29543907 |
| Evaluation of e-liquid toxicity using an open-source high-throughput screening assay. | PLoS Biol | 2018 Mar | 29584716 |
| Characterization of Nicotine Catabolism through a Novel Pyrrolidine Pathway in Pseudomonas sp. S-1. | J Agric Food Chem | 2018 Jul 18 | 29932673 |
| Alteration of adolescent aversive nicotine response and anxiety-like behavior in nicotine-exposed rats during late lactation period. | Behav Brain Res | 2018 Jan 30 | 28943427 |
| The GHR-R antagonist JMV 2959 neither induces malaise nor alters the malaiseproperty of LiCl in the adult male rat. | Physiol Behav | 2018 Jan 1 | 29056353 |
| Exenatide once weekly for smoking cessation: study protocol for a randomized clinical trial. | Medicine (Baltimore) | 2018 Jan | 29480848 |
| Evaluating oral flavorant effects on nicotine self-administration behavior andphasic dopamine signaling. | Neuropharmacology | 2018 Jan | 28943284 |
| Use Behaviors, Dependence, and Nicotine Exposure Associated with Ad Libitum CigarSmoking. | Tob Regul Sci | 2018 Jan | 29516029 |
| Competitive docking model for prediction of the human nicotinic acetylcholinereceptor α7 binding of tobacco constituents. | Oncotarget | 2018 Feb 8 | 29682193 |
| Effect of Charcoal in Cigarette Filters on Free Radicals in Mainstream Smoke. | Chem Res Toxicol | 2018 Aug 20 | 29979036 |
| Effect of imidacloprid ingestion on immune responses to porcine reproductive and respiratory syndrome virus. | Sci Rep | 2018 Aug 2 | 30072754 |
| Effective Message Elements for Disclosures About Chemicals in Cigarette Smoke. | Nicotine Tob Res | 2018 Aug 14 | 28521063 |
| Evaluation of flavourings potentially used in a heated tobacco product: Chemical analysis, in vitro mutagenicity, genotoxicity, cytotoxicity and in vitro tumour promoting activity. | Food Chem Toxicol | 2018 Aug | 29879435 |
| Comprehensive determination of flavouring additives and nicotine in e-cigaretterefill solutions. Part II: Gas-chromatography-mass spectrometry analysis. | J Chromatogr A | 2017 Sep 29 | 28859890 |
| Impact of e-liquid flavors on nicotine intake and pharmacology of e-cigarettes. | Drug Alcohol Depend | 2017 Sep 1 | 28704768 |
| Electronic Cigarettes: Their Constituents and Potential Links to Asthma. | Curr Allergy Asthma Rep | 2017 Oct 5 | 28983782 |