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Name |
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 | Hazard Symbols | T+,N,Xn,F,Xi | |
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 |
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.
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
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
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.
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. |