Piperazin Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
HYGROSKOPISCHE FARBLOSE KRISTALLEODER WEISSE FLOCKEN MIT STECHENDEM GERUCH.
CHEMISCHE GEFAHREN
Zersetzung beim Verbrennen unter Bildung giftiger und ätzender Gase mit Stickstoffoxiden. Mittelstarke Base in wässriger Lösung. Reagiert mit Säureanhydriden, starken Säurenund starken Oxidationsmitteln unter Feuergefahr. Greift viele Metalle unter Bildung brennbarer/explosionsfähiger Gase an (z.B. Wasserstoff, ICSC-Nr. 0001).
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK: IIb (nicht festgelegt, aber Informationen vorhanden); Sensibilisierung der Atemwege und der Haut (DFG 2006).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation und durch Verschlucken.
INHALATIONSGEFAHREN
Nur ungenügende Angaben vorhanden über die Geschwindigkeit, mit der eine gesundheitsschädliche Konzentration in der Luft beim Verdampfen bei 20°C erreicht wird.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz verätzt die Augen, die Haut und die Atemwege. ätzend beim Verschlucken. Inhalation der Substanz kann zu Lungenödem führen (s.Anm.). Möglich sind Auswirkungen auf das Nervensystem mit nachfolgenden Funktionsstörungenund Bewusstlosigkeit, wenn große Mengen verschluckt werden.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Wiederholter oder andauernder Kontakt kann zu Hautsensibilisierung führen. Wiederholte oder andauernde Inhalation kann asthmatische Beschwerden hervorrufen.
LECKAGE
Belüftung. Verschüttetes Material in abgedeckten Behältern sammeln; falls erforderlich durch Anfeuchten Staubentwicklung verhindern. Reste sorgfältig sammeln. An sicheren Ort bringen. NICHT in die Umwelt gelangen lassen. Persönliche Schutzausrüstung: Chemikalienschutzanzug mit umgebungsluftunabhängigem Atemschutzgerät.
R-Sätze Betriebsanweisung:
R34:Verursacht Verätzungen.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R52/53:Schädlich für Wasserorganismen, kann in Gewässern längerfristig schädliche Wirkungen haben.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz 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.
Beschreibung
Piperazine is contained in pyrazinobutazone, an equimolecular
sah of piperazine and phenylbutazone.
Among occupational cases, most were reported in the
pharmaceutical industry or laboratory, in nurses and
in veterinarians.
Chemische Eigenschaften
Piperazine is white to cream-colored needles or powder. Characteristic ammonia-like odor. Combustible solids that do not easily ignite.
Verwenden
Labelled Piperazine
Definition
ChEBI: An azacycloalkane that consists of a six-membered ring containing two nitrogen atoms at opposite positions.
Indications
Piperazine (Vermizine) contains a heterocyclic ring that
lacks a carboxyl group. It acts on the musculature of the
helminths to cause reversible flaccid paralysis mediated
by chloride-dependent hyperpolarization of the muscle
membrane. This results in expulsion of the worm.
Piperazine acts as an agonist at gated chloride channels
on the parasite muscle.
Piperazine has been used with success to treat A.
lumbricoides and E. vermicularis infections, although
mebendazole is now the agent of choice. Piperazine is
administered orally and is readily absorbed from the intestinal
tract. Most of the drug is excreted in the urine
within 24 hours.
Piperazine is an appropriate alternative to mebendazole
for the treatment of ascariasis, especially in the
presence of intestinal or biliary obstruction. Cure rates
of more than 80% are obtained following a 2-day regimen.
Side effects occasionally include gastrointestinal distress,
urticaria, and dizziness. Neurological symptoms of
ataxia, hypotonia, visual disturbances, and exacerbations of epilepsy can occur in patients with preexisting
renal insufficiency. It should not be used in pregnant
women because of the formation of a potentially carcinogenic
and teratogenic nitrosamine metabolite.
Concomitant use of piperazine and chlorpromazine or
pyrantel should be avoided.
Weltgesundheitsorganisation (WHO)
Piperazine was first used as a treatment for gout earlier this
century and its anthelminthic activity was discovered in 1949. It is also
considerably cheaper than other anthelminthic drugs. In some countries where
ascariasis is not endemic and where piperazine was used predominantly for the
treatment of pinworm it has been withdrawn from use on the grounds that other
more effective and less toxic drugs are now available (see full list). In other such
countries, however, piperazine remains available in over-the-counter preparations.
Clinical dosages occasionally induce transient neurological signs and concern has
been expressed that in some circumstances the drug may generate small amounts
of nitrosamine in the stomach. However, it is widely considered that these trace
doses are unlikely to give rise to a significant carcinogenic potential.
(Reference: (WHODIB) WHO Drug Information Bulletin, 1: 5, , 1983)
Allgemeine Beschreibung
Needle-like white or colorless crystals. Shipped as a solid or suspended in a liquid medium. Very corrosive to skin, eyes and mucous membranes. Solid turns dark when exposed to light. Flash point 190°F. Used as a corrosion inhibitor and as an insecticide.
Air & Water Reaktionen
Flammable. Absorbs water and carbon dioxide from air. Soluble in water.
Reaktivität anzeigen
1,4-Diazacyclohexane neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Absorbs carbon dioxide from the air, which can cause dry crystals to seem to melt. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. 1,4-Diazacyclohexane is sensitive to light; 1,4-Diazacyclohexane absorbs water and carbon dioxide from air. 1,4-Diazacyclohexane may be corrosive to aluminum, magnesium and zinc. .
Health Hazard
Piperazine is a corrosive substance. The solidand its concentrated aqueous solutions areirritants to the skin and eyes. The irritanteffect in rabbits’ eyes was severe.
The toxic symptoms from ingestion ofpiperazine include nausea, vomiting, excitement,change in motor activity, somnolence,and muscle contraction. The toxicity of thiscompound is low, however. The oral LD50value in rats is 1900 mg/kg. The inhalationtoxicity is very low. The inhalation LC50value in mice is 5400 mg/m
3/2 h.
Brandgefahr
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Pharmazeutische Anwendungen
A synthetic chemical, most commonly formulated as the citrate,
but also available as the adipate, edetate calcium and
tartrate salts.
Kontakt-Allergie
Piperazine is contained in pyrazinobutazone, an equimolar
salt of piperazine and phenylbutazone. Among occupational
cases, most were reported in the pharmaceutical
industry or laboratory workers, in nurses, and in
veterinarians.
Pharmakokinetik
Activity against intestinal worms requires that a substantial
amount remains in the gut. However, after oral administration
a variable amount is rapidly absorbed from the small
intestine and subsequently excreted in the urine. Its half-life
is extremely variable.
Clinical Use
Hexahydropyrazine or diethylenediamine (Arthriticine,Dispermin) occurs as colorless, volatile crystals of the hexahydratethat are freely soluble in water. After the discoveryof the anthelmintic properties of a derivative diethylcarbamazine,the activity of piperazine itself was established.Piperazine is still used as an anthelmintic for the treatmentof pinworm (Enterobius [Oxyuris] vermicularis) and roundworm(Ascaris lumbricoides) infestations. It is available invarious salt forms, including the citrate (official in the USP)in syrup and tablet forms. Piperazine blocks the response of the ascaris muscleto acetylcholine, causing flaccid paralysis in the worm,which is dislodged from the intestinal wall and expelled inthe feces.
Nebenwirkungen
Some people develop hypersensitivity, requiring cessation of
treatment. Transient, mild gastrointestinal or neurological
symptoms may occur.
Sicherheitsprofil
Moderately toxic by
ingestion, skin contact, intravenous, and
subcutaneous routes. Mildly toxic by
inhalation. A skin and severe eye irritant.
Excessive absorption can cause urticaria,
vomiting, diarrhea, blurred vision, and
weakness. Combustible when exposed to
heat or flame; can react vigorously with
oxidizing materials. Explodes on contact
with dicyanofurazan. To fight fire, use
alcohol foam, mist, dry chemical, water
spray. When heated to decomposition it
emits highly toxic fumes of NOx.
mögliche Exposition
(Piperazine): Primary irritant (w/o allergic reaction),
Carcinogenicity
No increase in lung adenomas
was produced in mice administered 0.69–18.75mg of piperazine/
kg in drinking water for 20–25 weeks and sacrificed
10–13 weeks later. Mice fed the equivalent of
938 mg/kg in the diet for 28 weeks and sacrificed at 40 weeks
failed to show any significant increase in the incidence of
lung adenomas. An increase in lung adenomas was
produced in this bioassay by administration of piperazine
together with sodium nitrate, suggesting the formation of the
active nitroso derivative. Sodium ascorbate inhibited
tumor formation, in theory, by preventing piperazine nitrosation
(304). Coadministration of 250 ppm piperazine and
500 ppm sodium nitrate in drinking water did not produce
tumors in rats. None of these studies were conducted
using currently accepted methods for evaluating carcinogenic
potential but piperazine alone, in these assays, was
noncarcinogenic.
Environmental Fate
This molecule has a simple chemical structure and molecular
weight of 86.14. It has a strong alkaline base soluble in water
(1:18), glycerol, and glycols, but is only sparingly soluble in
alcohol and insoluble in ether. Piperazine is not expected to
hydrolyze in water. The photodegradation half-life is approximately
0.8 h. The piperazine molecule is easily denaturalized
by diverse environmental factors and has a low potential for
bioaccumulation or biomagnification. To improve its stability,
it is usually formulated as different salts such as adipate, citrate,
phosphate, hexahydrate, and sulfate. Most piperazine salts are
white crystalline powders that are readily soluble in water.Exceptions are adipates, which dissolve to only a maximum
concentration of 5% in water, and phosphate, which is
insoluble.
Versand/Shipping
UN2579 Piperazine, Hazard class: 8; Labels: 8-Corrosive material.
läuterung methode
Piperazine crystallises from EtOH or anhydrous *benzene and is dried at 0.01mm. It can be sublimed under vacuum and purified by zone melting. The hydrochloride has m 172-174o (from EtOH), and the dihydrochloride crystallises from aqueous EtOH and has m 318-320o (dec, sublimes at 295-315o). The picrate has m ~200o, and the picrolonate crystallises from dimethylformamide ( m 259-261o). [Beilstein 23 H 4, 23 I 4, 23 II 3, 23 III/IV 15, 23/1 V 30.]
Inkompatibilitäten
Aqueous solution is a strong base. Violent reaction with strong oxidizers and dicyanofurazan. Incompatible with 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, nitrogen compounds, carbon tetrachloride. Attacks aluminum, copper, nickel, magnesium and zinc.
Piperazin Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
