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Substance Name: Nicotine [USP:BAN]
RN: 54-11-5
UNII: 6M3C89ZY6R
InChIKey: SNICXCGAKADSCV-JTQLQIEISA-N

Note

  • Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.

Molecular Formula

  • C10-H14-N2

Molecular Weight

  • 162.2346
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Autonomic Agents
  • Cholinergic Agents
  • Cholinergic Agonists
  • Ganglionic Stimulants
  • Human Data
  • Insecticide
  • Mutation Data
  • Natural Product
  • Neurotransmitter Agents
  • Nicotinic Agonists
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Smoking Cessation Adjunct

Superlist Classification Codes

  • Reportable Quantity (RQ) = 100 lb
  • Threshold Planning Quantity (TPQ) = 100 lb
  • TWA 0.5 mg/m3; skin

Names and Synonyms

Results Name

  • Nicotine [USP:BAN]

Name of Substance

  • Nicotine
  • Nicotine polacrilex [USAN]
  • Nicotine [BSI:ISO]
  • Nicotine [USP:BAN]

MeSH Heading

  • Nicotine

Synonyms

  • (-)-3-(1-Methyl-2-pyrrolidyl)pyridine
  • (-)-Nicotine
  • (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
  • (S)-Nicotine
  • 1-Methyl-2-(3-pyridyl)pyrrolidine
  • 3-(1-Methyl-2-pyrrolidinyl)pyridine
  • 3-(N-Methylpyrrolidino)pyridine
  • AI3-03424
  • beta-Pyridyl-alpha-N-methyl pyrrolidine
  • beta-Pyridyl-alpha-N-methylpyrrolidine
  • Black leaf
  • Black leaf 40
  • Caswell No. 597
  • CCRIS 1637
  • Destruxol orchid spray
  • EC 200-193-3
  • EINECS 200-193-3
  • Emo-nik
  • ENT 3,424
  • EPA Pesticide Chemical Code 056702
  • Exodus
  • Flux MAAG
  • Fumetobac
  • Habitrol
  • HSDB 1107
  • L-3-(1-Methyl-2-pyrrolidyl)pyridine
  • L-Nicotine
  • Mach-Nic
  • Micotine
  • Niagara P.A. dust
  • Nic-Sal
  • Nicabate
  • Nico-dust
  • Nico-fume
  • Nicocide
  • Nicoderm
  • Nicoderm CQ
  • Nicorette
  • Nicotin
  • Nicotina
  • Nicotina [Italian]
  • Nicotine
  • Nicotine alkaloid
  • Nicotine polacrilex
  • Nicotrol
  • Nicotrol Inhaler
  • Nicotrol NS
  • Nikotin
  • Nikotin [German]
  • Nikotyna
  • Nikotyna [Polish]
  • Niquitin
  • NSC 5065
  • Ortho N-4 and N-5 dusts
  • Ortho N-4 dust
  • Ortho N-5 dust
  • Prostep
  • Pyridine, 3-(tetrahydro-1-methylpyrrol-2-yl)
  • Pyrrolidine, 1-methyl-2-(3-pyridal)-
  • RCRA waste number P075
  • Tabazur
  • Tendust
  • Tetrahydronicotyrine, dl-
  • UNII-6M3C89ZY6R
  • XL all insecticide

Systematic Names

  • Nicotine
  • Pyridine, 3-((2S)-1-methyl-2-pyrrolidinyl)-
  • Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)- (9CI)

Superlist Names

  • Nicotine
  • Nicotine and salts
  • Nicotine [UN1654] [Poison]
  • Pyridine, 3-(1-methyl-2-pyrrolidinyl)-, (S)-
  • RCRA waste no. P075
  • UN1654

Registry Numbers

CAS Registry Number

  • 54-11-5

FDA UNII

  • 6M3C89ZY6R

Other Registry Numbers

  • 13890-81-8
  • 13890-82-9
  • 16760-37-5
  • 551-13-3
  • 6912-85-2

System Generated Number

  • 0000054115

Structure Descriptors

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

[C@H]1(c2cccnc2)N(CCC1)C

Toxicity

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) 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.
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: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

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: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA

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

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA		 Science. Vol. 127, Pg. 1054, 1958.
human TDLo rectal 1430ug/kg (1.43mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 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) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: TREMOR

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

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: TREMOR		 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: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Science. Vol. 127, Pg. 1054, 1958.
pig LDLo intramuscular > 14mg/kg (14mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Science. Vol. 127, Pg. 1054, 1958.
pigeon LDLo intramuscular 9mg/kg (9mg/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.
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) 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.
rabbit LDLo intramuscular 30mg/kg (30mg/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.
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) 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.
rat LDLo parenteral 34mg/kg (34mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 48, Pg. 317, 1933.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -7.90E+01 deg C   EXP
Boiling Point 247 deg C   EXP
pKa Dissociation Constant 3.1 (none)   EXP
log P (octanol-water) 1.17 (none)   EXP
Water Solubility 1.00E+06 mg/L   EXP
Henry's Law Constant 3.00E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.10E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.