Nicotine CAS 54-11-5
Introduction：Basic information about Nicotine CAS 54-11-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Nicotine Basic informationalkaloid Toxicity
| Product Name: | Nicotine |
| Synonyms: | (-)-3-(1-Methyl-2-pyrrolidyl)pyridine;(-)-3-(N-Methylpyrrolidino)pyridine;(S)-3-(1-Methyl-2-pyrrolidinyl)pyridine;1-methyl-2-(3-pyridal)-pyrrolidin;1-Methyl-2-(3-pyridiyl)pyrrolidine;BLACK LEAF 40;L(-)-NICOTINE;L-NICOTINE |
| CAS: | 54-11-5 |
| MF: | C10H14N2 |
| MW: | 162.23 |
| EINECS: | 200-193-3 |
| Product Categories: | Heterocycles;Mutagenesis Research Chemicals;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Chiral Reagents;BotanicalsPesticides&Metabolites;Alpha sort;Insecticides;N;NA - NI;N-PAlphabetic;Pesticides;Nicotine Derivatives;Alkaloids;Biochemistry;Pyridine Alkaloids |
| Mol File: | 54-11-5.mol |
Nicotine Chemical Properties
| Melting point | -80 °C |
| alpha | -166 º (c=neat) |
| Boiling point | 243-248 °C |
| density | 1.010 g/mL at 20 °C(lit.) |
| vapor pressure | 0.06 hPa (20 °C) |
| refractive index | n |
| Fp | 215 °F |
| storage temp. | 2-8°C |
| solubility | ethanol: 50 mg/mL |
| form | liquid |
| pka | 8.02(at 25℃) |
| color | yellow |
| PH | 10.2 (8.1g/l, H2O, 20°C) |
| explosive limit | 0.7-4%(V) |
| Odor Threshold | 0.011ppm |
| Optical Rotation | [α]20/D 169°(lit.) |
| Water Solubility | MISCIBLE |
| Sensitive | Air Sensitive & Hygroscopic |
| Merck | 14,6524 |
| BRN | 82109 |
| Exposure limits | TLV-TWA air 0.5 mg/m3 (ACGIH, MSHA,and OSHA). |
| Major Application | agriculture cleaning products cosmetics food and beverages personal care pharmaceutical (small molecule) |
| 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 |
| InChIKey | SNICXCGAKADSCV-JTQLQIEISA-N |
| SMILES | CN1CCC[C@H]1c2cccnc2 |
| LogP | 1.170 |
| CAS DataBase Reference | 54-11-5(CAS DataBase Reference) |
| NIST Chemistry Reference | 3-(2-(N-methylpyrrolidinyl))pyridine(54-11-5) |
| EPA Substance Registry System | Nicotine (54-11-5) |
Safety Information
| Hazard Codes | T+,N,Xn,F,Xi,T |
| Risk Statements | 25-27-51/53-36-20/21/22-11-36/37/38-39/23/24/25-23/24/25-59-48/20-40-36/38-24-20/22-63 |
| Safety Statements | 7-16-36/37-45-61-36-26-37/39-59 |
| RIDADR | UN 1654 6.1/PG 2 |
| OEB | C |
| OEL | TWA: 0.5 mg/m3 [skin] |
| WGK Germany | 3 |
| RTECS | QS5250000 |
| Autoignition Temperature | 240 °C |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | II |
| HS Code | 29399910 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Flam. Liq. 2 STOT SE 1 |
| Hazardous Substances Data | 54-11-5(Hazardous Substances Data) |
| Toxicity | LD50 in mice (mg/kg): 0.3 i.v.; 9.5 i.p.; 230 orally (Barlow, McLeod) |
| IDLA | 5 mg/m3 |
| alkaloid | Nicotine is the substance in tobacco, nicotine content of tobacco because there are different species and origin, alkali content of tobacco each part is different. Cigarette factory scraps (tobacco powder) containing about 1% to 2% of the nicotine, tobacco stems and ribs smoke nicotine containing about 1% or so, people smoked cigarette contains nicotine amounted to about 3%. Pure nicotine is a colorless, oily liquid, miscible with water below 60 ℃, hydrate, more than 210 ℃ also miscible with water. Unstable nature, likely to be volatile, soluble in water and organic solvents. Nicotine is an alkaloid, so all properties of a base, to a compound made of salts and acids. In case of light and air turn brown and sticky, there is the odd smell and strong irritant. |
| Toxicity | Pure nicotine for people, livestock highly toxic rat oral LD50 of 50~60mg/kg, rabbit acute percutaneous LD5050mg/kg. Rabbit acute percutaneous LD50 for 50~60mg/kg, rabbit acute oral LD50 of 50mg/kg. Based on China's pesticide toxicity grading standards, is a highly toxic pesticides. However, because of volatile and rapidly decompose in air and light, and therefore can still be used to control pests on crops. Rapidly absorbed through the skin, inhalation and dermal exposure to toxic people. Toxic to birds. Young steelhead LC504mg/L, toxic to bees, but there insecticide effect. D. Pulex LC50 of 0.24mg/L. Fish and shellfish toxicity, mild injury to crops. |
| Description | (–)-Nicotine is an alkaloid that has been found in tobacco. It is an agonist at neuronal nicotinic acetylcholine receptors (nAChRs) and binds to α3β4 and α4β2 subunit-containing nAChRs with Ki values of 481 and 11.1 nM, respectively. Chronic exposure to (–)-nicotine results in increased expression of certain nAChRs, particularly α4β2 subunit-containing nAChRs. (–)-Nicotine has addictive properties. Formulations containing (–)-nicotine have been used as smoking cessation aids for the relief of nicotine withdrawal symptoms. |
| Description | Nicotine is an alkaloid obtained from the dried leavesof Nicotiana tabacum and Nicotiana rustica. Nicotinestimulates acetylcholine receptors of the postsynapticmembrane at nerve synapses resulting in depolarizationof the membrane. Toxic doses cause stimulation that israpidly followed by blockade of nerve transmission. |
| Chemical Properties | Yellow Liquid |
| Chemical Properties | Nicotine is a pale yellow to dark brown, oilyliquid. Slight, fishy or pyridine-like odor when warm. It isalso available as a powder. |
| Originator | Nicotinell TTS,Novartis |
| Uses | Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer. |
| Uses | (S)-(-)-Nicotine is a prototype nicotinic acetylcholine receptor agonist. (S)-(-)-Nicotine is the naturally occurring isomer. Nicotine can be absorbed through the alimentary canal, respiratory tract and intact skin. Nicotine is used in the treatment of smoking withdrawal syndrome. Nicotine has been used as an anthelmintic. |
| Uses | Nicotine is one of the principal constituentsof tobacco. It occurs in the dried leavesof Nicotiana tabacum and Nicotiana rusticato the extent of 2–8%. Exposure risk tothis alkaloid arises from smoking, chewing,or inhaling tobacco. Nicotine and its saltsare used as insecticides and fumigants, intanning, and in medicine. |
| Uses | Nicotine is the second most widely used recreational drug after caffeine. At low doses, nicotineacts as a stimulant to the central nervous system by activating acetylcholine receptors, specifically called nicotinic acetylcholine receptors, in the postsynaptic neurons during nerve transmission.At higher doses nicotine acts as a depressant.Nicotine in tobacco has always been used for medicinal purposes. Nicotine solutions made from soaking tobacco leaves in water have been used as pesticides for several hundred years. In modern times, numerous pharmaceutical companies have explored nicotine's use for treating diseases. Nicotine's most prevalent medicinal use is for smoking cessation in the form of alternate delivery systems such as gums and dermal patches. Nicotine is used medically for numerous conditions and its use is being explored in additional areas including pain relievers, attention deficit disorder medications and medications associated with Alzheimer's disease, Parkinson disease, colitis, herpes, and tuberculosis. |
| Uses | Naturally-occuring isomer |
| Production Methods | The nicotine molecule consists of a pyrrolidine ring attached to a pyridine ring by a bondbetween carbon atoms in the two-ring systems. Nicotine was isolated in impure form fromtobacco in 1809 by Louis Nicholas-Vauquelin (1763–1829). Vauquelin called the substancenicotianine. In 1826, Wilhelm Posselt (1806–1877) and Karl Ludwig Reimann (1804–1872),medical students at Heidelberg University, isolated pure nicotine and published dissertationson its pharmacology in 1828. Louis Henri Melsens (1814–1886) determined nicotine’sempirical formula. Amé Pictet (1857–1937) and P. Crépieux reported the synthesis of nicotine in 1903. |
| Definition | A colourless poisonousalkaloid present in tobacco. It isused as an insecticide. |
| Definition | ChEBI: An optically active form of nicotine having S-configuration. |
| Manufacturing Process | The water extract from Nicotiana tabacum was prepared by distillation ofnicotine contained liquor from tobacco leaves, as described in D.R. Patent No.319,846; September 12, 1913. 5 kg this water extract or the same quantity of tobacco powder in water wasmixed with 1.5 kg of grinded calcium hydroxide and 1.5 kg calcium sulfate.The mixture stood for 24 hours. The obtained mixture looked like a drypowder. It was extracted with ether. The ether was distilled and the residuecontented 98% of clear nicotine - liquid with odor of pyridine; BP: 246C/735mm; d420 =1.0097; [α]d20=- 166.5. |
| Brand name | Habitrol (Novartis); Nicoderm (Sanofi Aventis); Nicotrol(Pharmacia & Upjohn); Prostep (Aveva). |
| Therapeutic Function | Ganglion depressant, Smoking deterrent |
| General Description | Liquids. Toxic by inhalation, ingestion, and skin absorption. More dense than water. Flash points usually below 140°F. Contact may irritate skin, eyes, and mucous membranes. If available, obtain the technical name of the material from the shipping papers and contact CHEMTREC, (800-424-9300) for specific response information. |
| Air & Water Reactions | Flammable. Slightly soluble in water. |
| Reactivity Profile | An alkaloid produced from tobacco. Colorless, oily liquid, combustible, highly toxic. When heated to decomposition L-Nicotine emits very toxic fumes of carbon monoxide and oxides of nitrogen [Lewis, 3rd ed., 1993, p. 919]. |
| Hazard | Toxic by ingestion, inhalation, and skinabsorption. Gastrointestinal damage, central nervous system impairment, and cardiac impairment |
| Health Hazard | Nicotine is a highly toxic compound. It stimulatesneuromuscular junctions and nicotinicreceptors, causing depression and paralysisof autonomic ganglia. Exposure routesare ingestion, absorption through skin, orinhalation (smoking or inhaling tobacco).The acute toxic symptoms in humansinclude nausea, vomiting, salivation, muscularweakness, twitching, and convulsions.The symptoms of confusion, hallucinations,and distorted perceptions have also beennoted in humans. Death may occur from respiratoryfailure. The lethal dose is approximately40 mg/kg. Chronic poisoning fromoccupational exposure may exhibit symptomsof vomiting and diarrhea. Fatal casesdue to occupational poisoning are unusual. Nicotine administered in animals producedtoxic symptoms that include somnolence,change in motor activity, ataxia, dyspnea,tremor, and convulsions. LD50 values, intraperitoneal (rats): 14.5 mg/kgLD50 values, oral (rats): 50 mg/kg Kramer and coworkers (1989) investigatedthe effect of nicotine on the accumulation ofdopamine in synaptic vesicles prepared frommouse cerebral cortex or bovine striatum. Itwas found to be a weak inhibitor of dopamineaccumulation. The role of nicotine in tobacco carcinogenesisis not yet fully understood. Nicotine is a precursor of N0-nitrosonornicotine , which is asuspected lung carcinogen (Hoffmann et al.1985). Nicotine-derived N-nitrosoaminescontribute significantly to carcinogenesiscaused by tobacco. However, there is noevidence in animals or humans of cancerscaused by nicotine itself. Berger and coworkers(1987) have found a beneficial effect ofperinatal nicotine administration in decreasingthe tumors of the neuorogenic systeminduced by N-methylnitrosourea in Sprague-Dawley rats. Although nicotineis noncarcinogenic, it acts as a cofactorin carcinogenesis induced by 7,12-dimethylbenz[a]anthracene in male Syrian goldenhamsters (Chen and Squier 1990). Nicotine produced teratogenic effects intest animals, causing postimplantation mortality,fetal death, and developmental abnormalities.Nicotine and its primary metabolitecotinine exhibited teratogenic potential withXenopus frog embryo teratogenesis assay(Dowson et al. 1988). Nicotine tested negative in the Neurosporacrassa –aneuploidy and histidinereversion–Ames tests for mutagenicity. |
| Health Hazard | L-Nicotine is classified as super toxic. Probable oral lethal dose in humans is less than 5 mg/kg or a taste (less than 7 drops) for a 70 kg (150 lbs.) person. It may be assumed that ingestion of 40-60 mg of nicotine is lethal to humans. There is fundamental difference between acute toxicity from use of nicotine as insecticide or from ingestion, and chronic toxicity that may be caused by prolonged exposure to small doses as occurs in smoking. Maternal smoking during pregnancy is associated with increased risk of spontaneous abortion, low birth weight and still-birth. Nicotine was found as a co-carcinogen in animals. |
| Fire Hazard | There is a moderate explosion hazard when exposed to heat or flame. When heated to decomposition, L-Nicotine emits nitrogen oxides, carbon monoxide and other highly toxic fumes. Avoid oxidizing materials. Stable under normal conditions. Avoid heat or flames. |
| Agricultural Uses | Insecticide: Nicotine is used in some drugs and insecticides.Classified for restricted use as an insecticide, limited to useby or under the direct supervision of a certified applicator.Not listed for use in EU countries. Registered for use inthe U.S. and Canada. A U.S. EPA restricted Use Pesticide(RUP). |
| Trade name | BLACK LEAF®; CAMPBELL'S NICOSOAP®; DESTRUXOL ORCHARD SPRAY®; EMONIB®; FLUX MAAG®; FUMETO-TENDUST®; BAC®;MACH-NIC®; NIAGARA P. A. DUST®; NICODUST®;NICOFUME®; NICOCIDE®; ORTHO N-4 DUST®; XLALL INSECTICIDE® |
| Potential Exposure | An alkaloid produced from tobacco.Nicotine is used in some drugs; and in tanning. At onetime, nicotine was used in the United States as an insecticideand fumigant; however, it is no longer produced orused in the United States for this purpose. |
| Carcinogenicity | Nicotine has low carcinogenicpotential. One study found that diets containing60 ppm nicotine and administered to rats for 300 daysreduced the growth rate. The authors concluded that reducedbody weight gains were only partially attributable to reducedfood intake. No pathology on the rats and no evidence ofcarcinogenicity were reported. Rats were injected subcutaneously(5 days/week) for 26 weeks followed by an approximate2-month observation period. Similarly, dogs wereinjected subcutaneously (5 days/week) for the same period.No tumors were observed in the test animals, althoughhyaline thickening and fibrosis of the vasculature of thekidney, lung, brain, and heart were evident. |
| Metabolic pathway | Nicotine has been used as an insecticide for at least 200 years but thisnaturally occurring compound lacks persistence and can be hazardous inuse (Corbett et al., 1984). It has been replaced with more effective syntheticinsecticides such as those in the neonicotinoid class. Most of the mformationon metabolism derives from research into the fate of nicotine aftertobacco smoking as well as from the use of nicotine in agriculture andhorticulture or through the biosynthesis of the alkaloid by plants andvegetables used as normal foodstuffs. Up to eight metabolites have beenisolated and identified in man with six primary pathways. The mainpathway is N-carbon oxidation of the pyrrolidine ring to form cotinine,others being N-oxidation of the pyrrolidine ring to form nicotine N-oxide,N-methylation of the pyridine ring to form an N-methylnicotinium ionand N-demethylation of the pyrrolidine ring to form nornicotine. Twoother pathways are formation of a nicotine enamhe and of a nicotineglucuronide (Gabrielsson and Gumbleton, 1993). There is little informationon the fate of nicotine in soil. |
| Metabolism | Nicotine is well absorbed from the mucous membranesin the oral cavity, gastrointestinal tract, and respiratorysystem. If tobacco smoke is held in the mouth for 2 seconds,66 to 77% of the nicotine in the smoke will be absorbedacross the oral mucosa. If tobacco smoke is inhaled,approximately 90 to 98% of the nicotine will beabsorbed. Nicotine is distributed throughout the body,readily crossing the blood-brain and placental barriers.The liver, kidney, and lung metabolize approximately 80to 90% of the alkaloid. The kidney rapidly eliminatesnicotine and its metabolites. |
| Shipping | UN1654 Nicotine, Hazard Class: 6.1; Labels:6.1-Poisonous materials. |
| Purification Methods | (-)-Nicotine is a very pale yellow hygroscopic oil with a characteristic odour (tobacco extract) which turns brown in air on exposure to light. It is purifed by fractional distillation under reduced pressure in an inert atmosphere. A freshly distilled sample should be stored in dark sealed containers under N2. It is a strong base; a 0.05 M aqueous solution has a pH of 10.2. It is very soluble in organic solvents. It is soluble in H2O and readily forms salts. [UV: Parvis J Chem Soc 97 1035 1910, Dobbie & Fox J Chem Soc 103 1194 1913.] The hydrochlorides (mono-and di-) form deliquescent crystals soluble in H2O and EtOH but insoluble in Et2O. It has also been purified via the ZnCl2 double salt. [Ratz Monatsh Chem 26 1241 1905, Biosynthesis: Nakan & Hitchinson J Org Chem 43 3922 1978.] The picrate has m 218o (from EtOH). [Beilstein 23/6 V 64.] POISONOUS. |
| Degradation | Nicotine is volatile and decomposes relatively quickly under the influenceof light and air. The pyrrolidine nitrogen (pka 8.2) is more basic than thepyridine moiety (pka 3.1) (PM). Nicotine has a chiral centre, and existsnaturally as the more potent (S) enantiomer. |
| Incompatibilities | Incompatible with strong oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates,chlorine, bromine, fluorine, etc.); contact may cause firesor explosions. Keep away from alkaline materials, strongbases, strong acids, oxoacids, epoxides. Incompatible withstrong acids. Attacks some forms of plastics, rubber, andcoatings. |
| Waste Disposal | Dissolve or mix the materialwith a combustible solvent and burn in a chemical incineratorequipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. In accordance with 40CFR165, followrecommendations for the disposal of pesticides and pesticidecontainers. Must be disposed properly by followingpackage label directions or by contacting your local orfederal environmental control agency, or by contactingyour regional EPA office. Consult with environmentalregulatory agencies for guidance on acceptable disposalpractices. Generators of waste containing this contaminant(≥100 kg/mo) must conform with EPA regulationsgoverning storage, transportation, treatment, and wastedisposal. |
| References | Pictet, Rotschy., Ber., 33, 2533 (1900) Tschitschibabin, Buchholz.,J. Russ. Phys. Chern. Soc., 50, 548 (1920) Spath, Biniecki., Ber., 72, 1809 (1939) Shmuk, Borozdina., CampI. rend. Acad. Sci., USSR, 12,1582 (1939) Shmuk, Borozdina., J. Appl. Chern. Russ., 14,864 (1941) Smith, Smith., J. Agric. Res., 65, 347 (1942) Pal, Narasinham.,!. Ind. Chern. Soc., 20, 181 (1943) Marion., Can. J. Res., 23B, 165 (1945) Bottomley, Nottle, White., Austral. J. Sci., 8, 18 (1945) Biosynthesis: Leete.,!. Amer. Chern. Soc., 89,7081 (1967) 14C-NMR spectrum: Ganz, Kelsey, Geiling., Bot. Gaz., 113, 195 (1951) 13C-NMR spectrum: Crain, Wilderman, Roberts., J. Amer. Chern. Soc., 93,990 (1971) Pharmacology : Rolleston., Lancet., 210,961 (1926) Laessing., Med. Welt., 12, 1485 (1938) Coon, Rothman., Proc. Soc. Exp. Bioi. Med., 42, 231 (1939) Straub, Amann., Klin. Woch., 19,169 (1940) Coon, Rothman., J. Pharm. Exp. Ther. Froc., 72, 9 (1941) Perlman, Dannesborg, Sokoloff., J. Amer. Med. Assoc., 120, 1003 (1942) Roth, McDonald, Sheard., ibid, 125,761 (1944) Burn, Truelove, Burn., Brit. Med. J., i, 403 (1945) |
Nicotine Preparation Products And Raw materials
| Raw materials | Calcium hydroxide-->calcium sulfate |
| Preparation Products | Nicotinic acid-->NORNICOTINE, DL-(RG)-->3-(4,5-DIHYDRO-1-METHYL-1H-PYRROL-2-YL)PYRIDINE-->(+/-)-NICOTINE |
