Substance
ID:69
Names and Identifiers
IUPAC name
3-(1-methylpyrrolidin-2-yl)pyridine
IUPAC Traditional name
nicotine
Brand Name
Nic-SalNicotrolNicotrol InhalerOrtho N-5 DustTendustBlack LeafEmo-NikFlux MaagCommitNicoderm CqNicotine PolacrilexNicotrol NsOrtho N-4 DustNikotinFumetobacNiagara P.A. DustNico-DustNico-FumeNicoretteNicotinNicorette PlusNicotinaNikotynaProstepBlack Leaf 40Campbell's Nico-SoapDestruxol Orchid SprayHabitrolMach-NicNicocideNicoderm
Synonyms
Nicotine AlkaloidL-NicotineNicotine
Properties
Physical Property
Solubility
1 g/mL
Hydrophobicity(logP)
1.1
Molecule Details
Drug Groups
approved
Description
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. [PubChem]
Indication
For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.
Pharmacology
Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.
Toxicity
Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD50= 24 mg/kg (orally in mice).
Affected Organisms
Humans and other mammals
Biotransformation
Primarily hepatic, cotinine is the primary metabolite.
Absorption
Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.
Half Life
Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours
Protein Binding
Less than 5%
Elimination
About 10% of the nicotine absorbed is excreted unchanged in the urine.
Distribution
* 2 to 3 L/kg
Clearance
* 1.2 L/min [healthy adult smoker]
References
•
Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4.
[Pubmed]
•
de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65.
[Pubmed]
•
de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5.
[Pubmed]
•
Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21.
[Pubmed]
External Links
Molecular Spectra
No Data Available
Click here to submit data
References
• de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. Pubmed
• Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. Pubmed
• de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. Pubmed
• Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. Pubmed