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L-Nicotine

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L-Nicotine

EINECS 200-193-3
CAS No. 54-11-5 Density 1.032 g/cm3
PSA 16.13000 LogP 1.78620
Solubility Miscible with water Melting Point -80 °C
Formula C10H14N2 Boiling Point 244.4 °C at 760 mmHg
Molecular Weight 162.235 Flash Point 101.7 °C
Transport Information UN 1654 6.1/PG 2 Appearance Yellow liquid
Safety 7-16-36/37-45-61-36-26-37/39 Risk Codes 25-27-51/53-36-20/21/22-11-36/37/38
Molecular Structure Molecular Structure of 54-11-5 (Nicotine) Hazard Symbols VeryT+,DangerousN,HarmfulXn,FlammableF,IrritantXi
Synonyms

Nicotine(8CI);Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)-;(-)-(S)-Nicotine;(-)-3-(1-Methyl-2-pyrrolidyl)pyridine;(-)-Nicotine;(-)-b-Pyridyl-a-N-methylpyrrolidine;(S)-(-)-Nicotine;(S)-3-(1-Methyl-2-pyrrolidinyl)pyridine;(S)-Nicotine;3-[(2S)-1-Methyl-2-pyrrolidinyl]pyridine;NSC 5065;Nicabate;Niconil;Nicolan;Nicopatch;

Article Data 57

L-Nicotine History

 Nicotine is named after the tobacco plant Nicotiana tabacum, which in turn is named after Jean Nicot de Villemain, French ambassador in Portugal, who sent tobacco and seeds from Brazil to Paris in 1560 and promoted their medicinal use. In 1828,Nicotine was first isolated from the tobacco plant by German chemists Posselt & Reimann, who considered it a poison.Its chemical empirical formula was described by Melsens in 1843, its structure was discovered by Garry Pinner in 1893, and it was first synthesized by Crepieux and A.Pictet  in 1904.

L-Nicotine Consensus Reports

EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

L-Nicotine Standards and Recommendations

OSHA PEL: TWA 0.5 mg/m3 (skin)
ACGIH TLV: TWA 0.5 mg/m3 (skin)
DFG MAK: 0.07 ppm; 0.47 mg/m3
DOT Classification:  6.1; Label: Poison

L-Nicotine Specification

The Nicotine with CAS registry number of 54-11-5 is also known as Pyridine, 3- (1-methyl-2-pyrrolidinyl)-, (S)-. The IUPAC name is 3-[(2S)-1-Methylpyrrolidin-2-yl]pyridine. It belongs to product categories of Nicotine Derivatives; Alkaloids; Biochemistry; Pyridine Alkaloids; Botanicals Pesticides&Metabolites; Alpha sort; Insecticides; N; NA-NI; N-PAlphabetic; Pesticides. Its EINECS registry number is 200-193-3. In addition, the formula is C10H14N2 and the molecular weight is 162.23. This chemical is a yellow liquid and should be stored in brown glass bottle in ventilated and dry place.

Physical properties about Nicotine are: (1)ACD/LogP: 0.72; (2)ACD/LogD (pH 5.5): -2.07; (3)ACD/LogD (pH 7.4): -0.47; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 3.82; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.539; (11)Molar Refractivity: 49.25 cm3; (12)Molar Volume: 157.1 cm3; (13)Surface Tension: 39.6 dyne/cm; (14)Density: 1.032 g/cm3; (15)Flash Point: 101.7 °C; (16)Enthalpy of Vaporization: 48.15 kJ/mol; (17)Boiling Point: 244.4 °C at 760 mmHg; (18)Vapour Pressure: 0.0303 mmHg at 25 °C.

Preparation of Nicotine: it is prepared by reaction of tobacco. Firstly, tobacco is dipped by acid and neutralized by alkali. Secondly, the reactant is distilled and dealed with oxalic acid. At last, product is obtained after alkalization.

Uses of Nicotine: it is used to produce 3-(1-methyl-pyrrolidin-2-yl)-pyridine. The reaction occurs with reagent NaH and solvent xylene with other condition of heating for 6 hours. The yield is about 66%. It also can be used as pesticide. What's more, this chemical can be quantified in blood, plasma, or urine to confirm a diagnosis of poisoning or to facilitate a medicolegal death investigation.

Nicotine is used to produce 3-(1-methyl-pyrrolidin-2-yl)-pyridine.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It's harmful and toxic by inhalation, in contact with skin and if swallowed. It's also toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep container tightly closed away from sources of ignition. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CN1CCCC1C2=CN=CC=C2
2. Isomeric SMILES: CN1CCC[C@H]1C2=CN=CC=C2
3. 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
4. InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LDLo intramuscular 8mg/kg (8mg/kg)   Physiological Zoology. Vol. 12, Pg. 238, 1939.
bird - wild LD50 oral 17800ug/kg (17.8mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LD50 intravenous 1300ug/kg (1.3mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 35, Pg. 316, 1936.
cat LDLo intramuscular 9mg/kg (9mg/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.
cat LDLo subcutaneous 20mg/kg (20mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
cattle LDLo intramuscular 9mg/kg (9mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Science. Vol. 127, Pg. 1054, 1958.
dog LD50 intravenous 5mg/kg (5mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 506, 1949.
dog LD50 oral 9200ug/kg (9.2mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932.
dog LDLo intramuscular 7700ug/kg (7.7mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932.
dog LDLo parenteral 5700ug/kg (5.7mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 1177, 1932.
dog LDLo subcutaneous 20mg/kg (20mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
frog LDLo subcutaneous 6mg/kg (6mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
guinea pig LD50 intravenous 4500ug/kg (4.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 11, Pg. 1011, 1961.
guinea pig LDLo intramuscular 15mg/kg (15mg/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.
guinea pig LDLo intraperitoneal 15mg/kg (15mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 50, Pg. 93, 1934.
guinea pig LDLo subcutaneous 15mg/kg (15mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 48, Pg. 95, 1933.
horse/donkey LDLo intramuscular 8800ug/kg (8.8mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
horse/donkey LDLo intramuscular 8800mg/kg (8800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Science. Vol. 127, Pg. 1054, 1958.
human TDLo rectal 1430ug/kg (1.43mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING
Clinical Toxicology. Vol. 10, Pg. 391, 1977.
mammal (species unspecified) LD50 intravenous 8mg/kg (8mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 406, 1971.
man LDLo unreported 882ug/kg (0.882mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
monkey LDLo intramuscular 6mg/kg (6mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
mouse LD50 intraperitoneal 5900ug/kg (5.9mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 227, 1974.
mouse LD50 intravenous 300ug/kg (0.3mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
British Journal of Pharmacology. Vol. 35, Pg. 161, 1969.
mouse LD50 oral 3340ug/kg (3.34mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Hygiene and Sanitation Vol. 34(4-6), Pg. 187, 1969.
mouse LD50 subcutaneous 16mg/kg (16mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 188, Pg. 605, 1938.
mouse LD50 unreported 260ug/kg (0.26mg/kg)   European Patent Application. Vol. #0000106,
mouse LDLo intramuscular 8mg/kg (8mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
pig LDLo intramuscular > 14mg/kg (14mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Science. Vol. 127, Pg. 1054, 1958.
pigeon LDLo intramuscular 9mg/kg (9mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
pigeon LDLo subcutaneous 4580ug/kg (4.58mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LD50 intraperitoneal 14mg/kg (14mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945.
rabbit LD50 intravenous 6250ug/kg (6.25mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945.
rabbit LD50 skin 50mg/kg (50mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Quarterly Bulletin--Association of Food and Drug Officials of the United States. Vol. 16, Pg. 3, 1952.
rabbit LDLo intramuscular 30mg/kg (30mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
rabbit LDLo subcutaneous 5mg/kg (5mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rat LD50 intraperitoneal 14560ug/kg (14.56mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 124, Pg. 350, 1958.
rat LD50 intratracheal 19300ug/kg (19.3mg/kg)   American Review of Respiratory Disease. Vol. 129, Pg. 112, 1984.
rat LD50 intravenous 2800ug/kg (2.8mg/kg)   Drugs in Japan Vol. -, Pg. 916, 1995.
rat LD50 oral 50mg/kg (50mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C219, 1991.
rat LD50 skin 140mg/kg (140mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 subcutaneous 25mg/kg (25mg/kg)   Farmakologiya i Toksikologiya Vol. 47(5), Pg. 85, 1984.
rat LDLo intraduodenal 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1037, 1975.
rat LDLo intramuscular 15mg/kg (15mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Science. Vol. 127, Pg. 1054, 1958.
rat LDLo parenteral 34mg/kg (34mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 48, Pg. 317, 1933.

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