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.
Reactivity Profile
An alkaloid produced from tobacco. Colorless, oily liquid, combustible, highly toxic. When heated to decomposition (-)-NICOTINE(54-11-5) emits very toxic fumes of carbon monoxide and oxides of nitrogen [Lewis, 3rd ed., 1993, p. 919].
Air & Water Reactions
Flammable. Slightly soluble in water.
Hazard
Toxic by ingestion, inhalation, and skin
absorption. Gastrointestinal damage, central nervous system impairment, and cardiac impairment
Health Hazard
(-)-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.
Potential Exposure
An alkaloid produced from tobacco.
Nicotine is used in some drugs; and in tanning. At one
time, nicotine was used in the United States as an insecticide
and fumigant; however, it is no longer produced or
used in the United States for this purpose.
Fire Hazard
There is a moderate explosion hazard when exposed to heat or flame. When heated to decomposition, (-)-NICOTINE emits nitrogen oxides, carbon monoxide and other highly toxic fumes. Avoid oxidizing materials. Stable under normal conditions. Avoid heat or flames.
First aid
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit.
Shipping
UN1654 Nicotine, Hazard Class: 6.1; Labels:
6.1-Poisonous materials.
Incompatibilities
Incompatible with strong oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, epoxides. Incompatible with
strong acids. Attacks some forms of plastics, rubber, and
coatings.
Description
(–)-Nicotine is an alkaloid that has been found in tobacco.
1 It is an agonist at neuronal nicotinic acetylcholine receptors (nAChRs) and binds to α3β4 and α4β2 subunit-containing nAChRs with K
i values of 481 and 11.1 nM, respectively.
1,2 Chronic exposure to (–)-nicotine results in increased expression of certain nAChRs, particularly α4β2 subunit-containing nAChRs.
3 (–)-Nicotine has addictive properties.
2,3 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 leaves
of Nicotiana tabacum and Nicotiana rustica. Nicotine
stimulates acetylcholine receptors of the postsynaptic
membrane at nerve synapses resulting in depolarization
of the membrane. Toxic doses cause stimulation that is
rapidly followed by blockade of nerve transmission.
Chemical Properties
Nicotine is a pale yellow to dark brown, oily
liquid. Slight, fishy or pyridine-like odor when warm. It is
also available as a powder.
Chemical Properties
Yellow Liquid
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator
equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed. In accordance with 40CFR165, follow
recommendations for the disposal of pesticides and pesticide
containers. Must be disposed properly by following
package label directions or by contacting your local or
federal environmental control agency, or by contacting
your regional EPA office. Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations
governing storage, transportation, treatment, and waste
disposal.
Originator
Nicotinell TTS,Novartis
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
Naturally-occuring isomer
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
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.
Definition
A colourless poisonousalkaloid present in tobacco. It isused as an insecticide.
Definition
ChEBI: An optically active form of nicotine having S-configuration.
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.
Manufacturing Process
The water extract from Nicotiana tabacum was prepared by distillation of
nicotine 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 was
mixed 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 dry
powder. It was extracted with ether. The ether was distilled and the residue
contented 98% of clear nicotine - liquid with odor of pyridine; BP: 246C/735
mm; d4
20 =1.0097; [α]d
20=- 166.5.
Brand name
Habitrol (Novartis); Nicoderm (Sanofi Aventis); Nicotrol
(Pharmacia & Upjohn); Prostep (Aveva).
Therapeutic Function
Ganglion depressant, Smoking deterrent
Agricultural Uses
Insecticide: Nicotine is used in some drugs and insecticides.
Classified for restricted use as an insecticide, limited to use
by or under the direct supervision of a certified applicator.
Not listed for use in EU countries. Registered for use in
the 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®; XL
ALL INSECTICIDE®
Carcinogenicity
Nicotine has low carcinogenic
potential. One study found that diets containing
60 ppm nicotine and administered to rats for 300 days
reduced the growth rate. The authors concluded that reduced
body weight gains were only partially attributable to reduced
food intake. No pathology on the rats and no evidence of
carcinogenicity were reported. Rats were injected subcutaneously
(5 days/week) for 26 weeks followed by an approximate
2-month observation period. Similarly, dogs were
injected subcutaneously (5 days/week) for the same period.
No tumors were observed in the test animals, although
hyaline thickening and fibrosis of the vasculature of the
kidney, lung, brain, and heart were evident.
Metabolic pathway
Nicotine has been used as an insecticide for at least 200 years but this
naturally occurring compound lacks persistence and can be hazardous in
use (Corbett et al., 1984). It has been replaced with more effective synthetic
insecticides such as those in the neonicotinoid class. Most of the mformation
on metabolism derives from research into the fate of nicotine after
tobacco smoking as well as from the use of nicotine in agriculture and
horticulture or through the biosynthesis of the alkaloid by plants and
vegetables used as normal foodstuffs. Up to eight metabolites have been
isolated and identified in man with six primary pathways. The main
pathway 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 ion
and N-demethylation of the pyrrolidine ring to form nornicotine. Two
other pathways are formation of a nicotine enamhe and of a nicotine
glucuronide (Gabrielsson and Gumbleton, 1993). There is little information
on the fate of nicotine in soil.
Metabolism
Nicotine is well absorbed from the mucous membranes
in the oral cavity, gastrointestinal tract, and respiratory
system. If tobacco smoke is held in the mouth for 2 seconds,
66 to 77% of the nicotine in the smoke will be absorbed
across the oral mucosa. If tobacco smoke is inhaled,
approximately 90 to 98% of the nicotine will be
absorbed. Nicotine is distributed throughout the body,
readily crossing the blood-brain and placental barriers.
The liver, kidney, and lung metabolize approximately 80
to 90% of the alkaloid. The kidney rapidly eliminates
nicotine and its metabolites.
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 influence
of light and air. The pyrrolidine nitrogen (pka 8.2) is more basic than the
pyridine moiety (pka 3.1) (PM). Nicotine has a chiral centre, and exists
naturally as the more potent (S) enantiomer.
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)
