Nikotin Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
öLIGE, FARBLOSE HYGROSKOPISCHE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH. VERFäRBT SICH BRAUN BEI KONTAKT MIT LUFT.
CHEMISCHE GEFAHREN
Zersetzung beim Erhitzen unter Bildung giftiger Rauche mit Stickstoffoxiden und Kohlenmonoxid. Reagiert sehr heftig mit starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV: 0,5 mg/m?(als TWA); Hautresorption; (ACGIH 2005).
MAK: IIb (nicht festgelegt, aber Informationen vorhanden); Hautresorption; (DFG 2008).
EG Arbeitsplatz-Richtgrenzwerte: 0.5 mg/m?(als TWA); Hautresorption; (EG 2006)
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation, über die Haut und durch Verschlucken.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt die Augen und die Haut. Möglich sind Auswirkungen auf Herzkreislaufsystem und Zentralnervensystem mit nachfolgenden Krämpfen und Atemversagen. Exposition weit oberhalb der Arbeitsplatzgrenzwerte kann zum Tod führen. Die Auswirkungen treten u.U. verzögert ein. ärztliche Beobachtung notwendig.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Tierversuche zeigen, dass die Substanz möglicherweise fruchtbarkeitsschädigend oder entwicklungsschädigend wirken kann.
LECKAGE
Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. NICHT in die Kanalisation spülen. Persönliche Schutzausrüstung: Vollschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R27:Sehr giftig bei Berührung mit der Haut.
R51/53:Giftig für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R11:Leichtentzündlich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S7:Behälter dicht geschlossen halten.
S16:Von Zündquellen fernhalten - Nicht rauchen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S61:Freisetzung in die Umwelt vermeiden. Besondere Anweisungen einholen/Sicherheitsdatenblatt zu Rate ziehen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
(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.
Definition
ChEBI: An optically active form of nicotine having S-configuration.
Vorbereitung Methode
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.
Allgemeine Beschreibung
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.
Air & Water Reaktionen
Flammable. Slightly soluble in water.
Reaktivität anzeigen
An alkaloid produced from tobacco. Colorless, oily liquid, combustible, highly toxic. When heated to decomposition L-Nicotine emits very toxic fumes of carbon monoxide and oxides of nitrogen [Lewis, 3rd ed., 1993, p. 919].
Hazard
Toxic by ingestion, inhalation, and skin
absorption. Gastrointestinal damage, central nervous system impairment, and cardiac impairment
Health Hazard
L-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.
Brandgefahr
There is a moderate explosion hazard when exposed to heat or flame. When heated to decomposition, L-Nicotine emits nitrogen oxides, carbon monoxide and other highly toxic fumes. Avoid oxidizing materials. Stable under normal conditions. Avoid heat or flames.
Landwirtschaftliche Anwendung
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).
Handelsname
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®
mögliche Exposition
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.
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.
Stoffwechselwegen
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.
Stoffwechsel
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.
Versand/Shipping
UN1654 Nicotine, Hazard Class: 6.1; Labels:
6.1-Poisonous materials.
läuterung methode
(-)-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.
Inkompatibilitäten
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.
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.
Einzelnachweise
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)
Nikotin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
