(S)-(-)-nicotine

General Material Information

Preferred name	(S)-(-)-nicotine
Trivial Name	(-)-Nicotine
Short Description	pyridine, 3- (1-methyl-2-pyrrolidinyl)-, (S)-
Formula	C10 H14 N2
CAS Number	54-11-5
Deleted CAS Number	13890-81-8
ECHA Number	200-193-3
FDA UNII	6M3C89ZY6R
Nikkaji Number	J9.266E
Beilstein Number	082109
MDL	MFCD00006369
Bio Activity Summary	External link
NMR Predictor	External link
Synonyms	destruxol emo-nik flux MAAG fumeto bac fumetobac habitrol mach-nic 1-methyl-2-(3-pyridyl)pyrrolidine (S)-3-(1-methyl-2-pyrrolidinyl)pyridine 3-[(2S)-1-methyl-2-pyrrolidinyl]pyridine L-3-(1-methyl-2-pyrrolidyl)pyridine 3-((S)-1-methyl-pyrrolidin-2-yl)-pyridine (S)-3-(1-methylpyrrolidin-2-yl)pyridine (S)-3-(N- methylpyrrolidin-2-yl)pyridine 3-((2S)-1-methylpyrrolidin-2-yl)pyridine 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine micotine nic-sal nico-dust nico-fume nicocide nicoderm niconil nicotin (-)- nicotine (S)- nicotine L- nicotine L-(-)- nicotine S-(-)- nicotine nicotrol prostep pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)- pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- pyridine, 3-[(2S)-1-methyl-2-pyrrolidinyl]- b- pyridyl-a-N-methylpyrrolidine tendust Nicotine 3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine (-)-3-(1-Methyl-2-pyrrolidyl)pyridine l-Nicotine (-)-Nicotine (-)-β-Pyridyl-α-N-methylpyrrolidine XL All Insecticide Nicotinell (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine Nicorette (S)-Nicotine Nicopatch Nicotell TTS Nicabate Nicolan Tabazur NSC 5065 (-)-(S)-Nicotine Exodus Nikofrenon Niquitin 3-[(2S)-1-Methylpyrrolidin-2-yl]pyridine MeSH ID: D009538

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Literature & References

Leffingwell:	Chirality or Article
	3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	89594
Pubchem (sid):	134971645

Publications by PubMed
Nicotine concentrations with electronic cigarette use: effects of sex and flavor.
Factors associated with electronic cigarette users' device preferences and transition from first generation to advanced generation devices.
Multicomponent Analysis of Replacement Liquids of Electronic Cigarettes Using Chromatographic Techniques.
Vapors produced by electronic cigarettes and e-juices with flavorings induce toxicity, oxidative stress, and inflammatory response in lung epithelial cells and in mouse lung.
Chemical Composition and Evaluation of Nicotine, Tobacco Alkaloids, pH, and Selected Flavors in E-Cigarette Cartridges and Refill Solutions.
Custom Mentholation of Commercial Cigarettes for Research Purposes.
The Impact of Flavor Descriptors on Nonsmoking Teens' and Adult Smokers' Interest in Electronic Cigarettes.
E-Cigarette Market Trends in Traditional U.S. Retail Channels, 2012-2013.
Patterns of Longitudinal Transitions in Menthol Use Among U.S. Young Adult Smokers.
Aerosol deposition doses in the human respiratory tree of electronic cigarette smokers.
Comparison of select analytes in aerosol from e-cigarettes with smoke from conventional cigarettes and with ambient air.
Identification and Quantification of Several Contaminated Compounds in Replacement Liquids of Electronic Cigarettes by Gas Chromatography-Mass Spectrometry.
Comparative in vitro toxicity profile of electronic and tobacco cigarettes, smokeless tobacco and nicotine replacement therapy products: e-liquids, extracts and collected aerosols.
Comparison of Puff Topography, Toxicant Exposure, and Subjective Effects in Low- and High-Frequency Waterpipe Users: A Double-Blind, Placebo-Control Study.
The association between smokers' perceived importance of the appearance of cigarettes/cigarette packs and smoking sensory experience: a structural equation model.
Evaluation of electronic cigarette liquids and aerosol for the presence of selected inhalation toxins.
Prenatal alcohol exposure increases postnatal acceptability of nicotine odor and taste in adolescent rats.
Investigation of the chemical compositions in tobacco of different origins and maturities at harvest by GC-MS and HPLC-PDA-QTOF-MS.
Comparative effects between electronic and cigarette smoke in human keratinocytes and epithelial lung cells.
Oxidative and pro-inflammatory impact of regular and denicotinized cigarettes on blood brain barrier endothelial cells: is smoking reduced or nicotine-free products really safe?
The role of cocoa as a cigarette additive: opportunities for product regulation.
Direct action and modulating effect of (+)- and (-)-nicotine on ion channels expressed in trigeminal sensory neurons.
Comparison of tobacco-containing and tobacco-free waterpipe products: effects on human alveolar cells.
Comparison of electronic cigarette refill fluid cytotoxicity using embryonic and adult models.
Flavored and nonflavored smokeless tobacco products: rate, pattern of use, and effects.
Youth access, creation, and content of smokeless tobacco ("dip") videos in social media.
Does switching to a tobacco-free waterpipe product reduce toxicant intake? A crossover study comparing CO, NO, PAH, volatile aldehydes, "tar" and nicotine yields.
Electronic cigarettes: effective nicotine delivery after acute administration.
Scientific assessment of the use of sugars as cigarette tobacco ingredients: a review of published and other publicly available studies.
Use of the target group index survey to evaluate the cigarette smoking profile in Saudi Arabia.
Effect of ammonia in cigarette tobacco on nicotine absorption in human smokers.
The health effects of menthol cigarettes as compared to non-menthol cigarettes.
Acute effects of waterpipe tobacco smoking: a double-blind, placebo-control study.
Determination of hazardous VOCs and nicotine released from mainstream smoke by the combination of the SPME and GC-MS methods.
The effect of chewing gum flavor on the negative affect associated with tobacco abstinence among dependent cigarette smokers.
Cellular basis for the olfactory response to nicotine.
The effect of chewing gum on self-reported nicotine withdrawal: is it the flavor, the act of chewing, or both?
Comparison of methods for measurement of smoking behavior: mouthpiece-based computerized devices versus direct observation.
Surveillance of moist snuff: total nicotine, moisture, pH, un-ionized nicotine, and tobacco-specific nitrosamines.
A randomized, controlled exposure study in adult smokers of full flavor Marlboro cigarettes switching to Marlboro Lights or Marlboro Ultra Lights cigarettes.
The menthol smoker: tobacco industry research on consumer sensory perception of menthol cigarettes and its role in smoking behavior.
Genotoxicity of 10 cigarette smoke condensates in four test systems: comparisons between assays and condensates.
Internal tobacco industry research on olfactory and trigeminal nerve response to nicotine and other smoke components.
Toxicological evaluation of potassium sorbate added to cigarette tobacco.
Do increases in cigarette prices lead to increases in sales of cigarettes with high tar and nicotine yields?
Determination of 10 carcinogenic polycyclic aromatic hydrocarbons in mainstream cigarette smoke.
Cytotoxicity and gene expression profiles in cell cultures exposed to whole smoke from three types of cigarettes.
Cadmium, lead, and thallium in mainstream tobacco smoke particulate.
Characterization of measured menthol in 48 U.S. cigarette sub-brands.
Toxicological evaluation of glycerin as a cigarette ingredient.
Scope for regulation of cigarette smoke toxicity according to brand differences in published toxicant emissions.
Smoking topography predicts abstinence following treatment with nicotine replacement therapy.
Adolescent and adult rats' aversion to flavors previously paired with nicotine.
Extinguishing the rewarding value of smoke cues: pharmacological and behavioral treatments.
Application, function, and effects of menthol in cigarettes: a survey of tobacco industry documents.
Efficacy of oral transmucosal nicotine lozenge for suppression of withdrawal symptoms in smoking abstinence.
Relationship between FTC 'tar' and urine mutagenicity in smokers of tobacco-burning or Eclipse cigarettes.
Flavor improvement does not increase abuse liability of nicotine chewing gum.
Subjective and discriminative stimulus effects of two de-nicotinized cigarettes with different tar yields.
Acute effects of smoking of cigarettes with different tar content on plasma oxidant/antioxidant status.
Toxicologic evaluation of flavor ingredients added to cigarette tobacco: skin painting bioassay of cigarette smoke condensate in SENCAR mice.
Indian cigarettes gain popularity, but don't let the flavor fool you.
Glass fiber contamination of cigarette filters: an additional health risk to the smoker?
Preferences for tastes paired with a nicotine antagonist in rats chronically treated with nicotine.
Genetic differences in nicotine-induced conditioned taste aversion.
Comparison of measured and FTC-predicted nicotine uptake in smokers.
Nicotine and addiction. The Brown and Williamson documents.
Rewarding drugs produce taste avoidance, but not taste aversion.
Nicotine polacrilex dose effects: serum nicotine levels and sensory characteristics.
Clinical evaluation of a citric acid inhaler for smoking cessation.
The use of flavor in cigarette substitutes.
Withdrawal from chronic nicotine fails to produce a conditioned taste aversion to saccharin in rats.
Development of a citric acid aerosol as a smoking cessation aid.
Neuromuscular disorder associated with a defect in mitochondrial energy supply.

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
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(IUPAC):	Periodic Table of the Elements
CHEBI:	View
CHEMBL:	View
Golm Metabolome Database:	Search
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UM BBD:	Search
KEGG (GenomeNet):	C00745
HMDB (The Human Metabolome Database):	HMDB01934
Export Tariff Code:	2939.70.0000
MedlinePlusSupp:	View
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: •preparations: (ahfs, 2009) nicotine preparations: route dosage forms strengths brand names nasal solution 0.5 mgmetered spray nicotrol ns (with parabens); pfizer oral inhalation inhalant 4 mgmetered spray nicotrol inhalaer; pfizer topical transdermal system 15 mg16 hours (8.3 mg10 sq cm) nicotrol step 1; pfizer transdermal system 10 mg16 hours (16.6 mg10 sq cm) nicotrol step 2; pfizer transdermal system 15 mg16 hours (24.9 mg30 sq cm) nicotrol step 3; pfizer transdermal system 7 mg24 hours nicotine transdermal system; sano, watson transdermal system 7 mg24 hours (36 mg7 sq cm) nicoderm cq clear step 3; glaxosmithkline transdermal system 11 mg24 hours nicotine transdermal system; perrigo transdermal system 14 mg24 hours nicotine transdermal system; sano, watson transdermal system 14 mg24 hours (78 mg15 sq cm) nicoderm cq clear step 3; glaxosmithkline transdermal system 21 mg24 hours nicotine transdermal system; sano, watson transdermal system 21 mg24 hours (114 mg22 sq cm) nicoderm cq step 1; glaxosmithkline buccal (transmucosal) lozenges 2 mg (of nicotine) commit (with aspartame); glaxosmithkline lozenges 4 mg (of nicotine) commit (with aspartame); glaxosmithkline pieces, chewing gum 2 mg (of nicotine) nicorette (sugar-free); glaxosmithkline pieces, chewing gum 4 mg (of nicotine) nicorette ds (sugar-free); glaxosmithkline pieces, chewing gum 4 mg (of nicotine) nicotine polacrilex gum; perrigo, watson •available as the dihydrochloride, salicylate, sulfate, and bitartrate •available commercially as the (-)-enantiomer sulfate salt •fumigant; soluble concentrate

Suppliers

Alfa Biotechnology	Glentham Life Sciences
M&U International	Penta International
Sigma-Aldrich: Sigma	WholeChem
Glentham Life Sciences Ltd	M&U International LLC
Penta International Corporation	WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	162.23558044434
Specific gravity	@ 25 °C
Pounds per Gallon
Vapor Pressure	0.03 mmHg @ 25 °C
Vapor Density	5.61
Flash Point TCC Value	101.67 °C TCC
logP (o/w)	1.17
Solubility
water, 1.00E+06 mg/L @ 25 °C (exp)	Yes
water, 1e+006 mg/L @ 25 °C (est)	Yes

Safety Information

Safety information

Preferred SDS: View

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50 17800 ug/kg Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. intravenous-cat LD50 1300 ug/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 316, 1936. intramuscular-cat LDLo 9 mg/kg PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Science. Vol. 127, Pg. 1054, 1958. intramuscular-cattle LDLo 9 mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Science. Vol. 127, Pg. 1054, 1958. intravenous-dog LD50 5 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 506, 1949. oral-dog LD50 9200 ug/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932. intramuscular-dog LDLo 7700 ug/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932. parenteral-dog LDLo 5700 ug/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932. intravenous-guinea pig LD50 4500 ug/kg Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 1011, 1961. intramuscular-guinea pig LDLo 15 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Science. Vol. 127, Pg. 1054, 1958. intraperitoneal-guinea pig LDLo 15 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 50, Pg. 93, 1934. intravenous-mammal (species unspecified) LD50 8 mg/kg "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 406, 1971. unreported-man LDLo 882 ug/kg "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. intraperitoneal-mouse LD50 5900 ug/kg Toxicology and Applied Pharmacology. Vol. 28, Pg. 227, 1974. intravenous-mouse LD50 300 ug/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Journal of Pharmacology. Vol. 35, Pg. 161, 1969. oral-mouse LD50 3340 ug/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) BEHAVIORAL: TREMOR Hygiene and Sanitation Vol. 34(4-6), Pg. 187, 1969. unreported-mouse LD50 260 ug/kg European Patent Application. Vol. #0000106 intramuscular-mouse LDLo 8 mg/kg PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Science. Vol. 127, Pg. 1054, 1958. intraperitoneal-rabbit LD50 14 mg/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945. intravenous-rabbit LD50 6250 ug/kg Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945. intramuscular-rabbit LDLo 30 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Science. Vol. 127, Pg. 1054, 1958. intraperitoneal-rat LD50 14560 ug/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 124, Pg. 350, 1958. intratracheal-rat LD50 19300 ug/kg American Review of Respiratory Disease. Vol. 129, Pg. 112, 1984. intravenous-rat LD50 2800 ug/kg Drugs in Japan Vol. -, Pg. 916, 1995. oral-rat LD50 50 mg/kg Farm Chemicals Handbook. Vol. -, Pg. C219, 1991. intramuscular-rat LDLo 15 mg/kg BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Science. Vol. 127, Pg. 1054, 1958. parenteral-rat LDLo 34 mg/kg LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 48, Pg. 317, 1933.
Dermal Toxicity:
subcutaneous-cat LDLo 20 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. subcutaneous-dog LDLo 20 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. subcutaneous-frog LDLo 6 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. subcutaneous-guinea pig LDLo 15 mg/kg BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA Journal of Pharmacology and Experimental Therapeutics. Vol. 48, Pg. 95, 1933. subcutaneous-mouse LD50 16 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 188, Pg. 605, 1938. skin-rabbit LD50 50 mg/kg LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Quarterly Bulletin--Association of Food and Drug Officials of the United States. Vol. 16, Pg. 3, 1952. subcutaneous-rabbit LDLo 5 mg/kg "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931. skin-rat LD50 140 mg/kg World Review of Pest Control. Vol. 9, Pg. 119, 1970. subcutaneous-rat LD50 25 mg/kg Farmakologiya i Toksikologiya Vol. 47(5), Pg. 85, 1984.
Inhalation Toxicity:
Not determined

Safety in use information

Category:
pharmaceuticals / chemical synthisis
Recommendation for (S)-(-)-nicotine usage levels up to:
	not for fragrance use.

Recommendation for (S)-(-)-nicotine flavor usage levels up to:
	not for flavor use.