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Penicillamin

D-Penicillamine Struktur
52-67-5
CAS-Nr.
52-67-5
Bezeichnung:
Penicillamin
Englisch Name:
D-Penicillamine
Synonyma:
PENICILLAMINE;Penicillamin;2-Amino-3-mercapto-3-methylbutanoic acid;(S)-2-aMino-3-Mercapto-3-Methylbutanoic acid;Pencillamine;usan;H-D-PEN-OH;Depen;D-Pen-OH;Cuprimine
CBNumber:
CB5742367
Summenformel:
C5H11NO2S
Molgewicht:
149.21
MOL-Datei:
52-67-5.mol

Penicillamin Eigenschaften

Schmelzpunkt:
210 °C (dec.)(lit.)
Siedepunkt:
251.8±35.0 °C(Predicted)
alpha 
-65 º (c=5, 1M NaOH, on dry)
Dichte
1.113 (estimate)
Brechungsindex
-63 ° (C=1, 1mol/L NaOH)
storage temp. 
2-8°C
L?slichkeit
H2O: soluble100mg/mL
Aggregatzustand
Powder
pka
pKa 7.83±0.01(H2O,t =37±0.05,I=0.15)(Approximate)
Farbe
White to almost white
Optische Rotation
-6325 (pyridine), L-form: +6325 (1 mol dm-3 NaOH)
Wasserl?slichkeit
11.1 g/100 mL (20 ºC)
Merck 
14,7088
BRN 
1722375
BCS Class
3
Stabilit?t:
Stable. Incompatible with strong oxidizing agents.
InChI
1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChIKey
VVNCNSJFMMFHPL-VKHMYHEASA-N
SMILES
CC(C)(S)[C@@H](N)C(O)=O
CAS Datenbank
52-67-5(CAS DataBase Reference)
NIST chemische Informationen
Penicillamine(52-67-5)
EPA chemische Informationen
Penicillamine (52-67-5)

Sicherheit

Kennzeichnung gef?hrlicher Xi,T,Xn
R-S?tze: 36/37/38-40-20/21/22
S-S?tze: 26-36-24/25-22
WGK Germany  2
RTECS-Nr. YV9425000
Hazard Note  Toxic
HS Code  29309016
Speicherklasse 11 - Combustible Solids
Hazard Classifications Repr. 2
Giftige Stoffe Daten 52-67-5(Hazardous Substances Data)
Toxizit?t LD50 in rats (mg/kg): >10000 orally, >660 i.p. (Jaffe)

Penicillamin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.

S-S?tze Betriebsanweisung:

S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S22:Staub nicht einatmen.

Beschreibung

Penicillamine is an orally bioavailable copper chelator and penicillin degradation product. It increases urinary and fecal copper excretion and decreases liver copper concentration in a rat model of copper overload when administered at 0.67 mmol/kg per day, but does not affect kidney, spleen, or brain copper levels. Penicillamine (100 mg/kg per day) dissolves copper-rich granules in hepatic lysosomes of Long-Evans cinnamon (LEC) rats, which spontaneously develop hepatic injury and acute hepatitis and have a mutation homologous to that of the human Wilson disease gene. Penicillamine has anticonvulsant and proconvulsant effects in mice when administered at 0.5 and 250 mg/kg, respectively, which are blocked by the nitric oxide synthase (NOS) inhibitors L-NAME and 7-nitroindazole . Formulations containing penicillamine have been used to treat Wilson disease, cystinuria, and active rheumatoid arthritis.

Chemische Eigenschaften

White to off-white crystalline powder

Verwenden

As a Penicillin metabolite, D-(-)-Penicillamin can be used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

Definition

ChEBI: An optically active form of penicillamine having D-configuration. Pharmaceutical form (L-form is toxic) of chelating agent used to treat heavy metal poisoning.

Allgemeine Beschreibung

D-Penicillamine contains a β-lactam chemical structure.

Sicherheitsprofil

Poison by intraperitoneal route. Moderately toxic by subcutaneous and intravenous routes. Mildly toxic by ingestion. An experimental teratogen. Human systemic effects by ingestion: agranulocytosis, dermatitis, fever, hemorrhage, increased body temperature, dermatitis, leukopenia, proteinuria, thrombocytopenia. Human teratogenic effects by an unspecified route: developmental abnormalities of the craniofacial areas, skin, and skin appendages, and body wall. Experimental reproductive effects. Questionable human carcinogen producing leukemia. Mutation data reported. Used in the treatment of rheumatoid arthritis, metal poisonings, and cystinuria. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

Synthese

d-penicillamine can be synthesized in a multistep process that begins with heating isobutyraldehyde, pyridine, sulfur, and ammonia in benzene to form 5,5-dimethyl-2- isopropyl-3-thiazoline. Treatment with hydrogen cyanide gives 4-cyano-5,5-dimethyl- 2-isopropylthiazolidine, which on acid hydrolysis gives d,l-penicillamine hydrochloride. Resolution is accomplished by conversion of the racemate to d,l-3-formyl- 2,2,5,5-tetramethylthiazolidine-4-carboxylic acid by treatment first with acetone, then with acetic formic anhydride. The enantiomers are separated in the usual manner, using, for example, l-lysine or d-()- threo-1-(4-nitrophenyl)-2-aminopropane-1,3- diol. Acidification liberates d-3-formyl- 2,2,5,5-tetramethylthiazolidine-4-carboxylic acid, which is hydrolyzed with hydrochloric acid to yield d-penicillamine hydrochloride. Neutralization with ethanolic triethylamine affords d-penicillamine.
D-Penicillamine synthesis

l?uterung methode

The melting point of D-(-)-penicillamine depends on the rate of heating (m 202-206o is obtained by starting at 195o and heating at 2o/minute). It is soluble in H2O and alcohols but insoluble in Et2O, CHCl3, CCl4 and hydrocarbon solvents. Purify it by dissolving it in MeOH and adding Et2O slowly. Dry it in vacuo and store it under N2. [Weight et al. Angew Chem, Int Ed (English) 14 330 1975, Cornforth in The Chemistry of Penicillin (Clarke, Johnson and Robinson eds) Princeton Univ Press, 455 1949, Review: Chain et al. Antibiotics (Oxford University Press) 2 1949, Polymorphism: Vidler J Pharm Pharmacol 28 663 1976]. The D-S-benzyl derivative has m 197-198o (from H2O), [] D 17 -20o (c 1, N NaOH), -70o (N HCl). [Beilstein 4 IV 3228.]

Penicillamin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Penicillamin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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52-67-5(Penicillamin)Verwandte Suche:


  • (S)-Penicillamine
  • 3-mercapto-d-valin
  • 3-Sulfanylvaline
  • alpha-amino-beta-methyl-beta-mercaptobutyricacid
  • Artamine
  • beta,beta-Dimethylcysteine
  • beta-mercaptovaline
  • beta-Thiovaline
  • reducedd-penicillamine
  • reducedpenicillamine
  • Sufirtan
  • Trolovol
  • Valine, 3-mercapto-, D-
  • (S)-2-AMINO-3-MERCAPTO-3-METHYL-BUTYRIC ACID
  • PENICILLAMINE(D-)
  • D-BETA-MERCAPTOVALINE
  • D-BETA,BETA-DIMETHYLCYSTEINE
  • D(-)-2-AMINO-3-MERCAPTO-3-METHYLBUTANOIC ACID
  • D[-]-2-AMINO-3-MERCAPTO-3-METHYLBUTANOIC ACID
  • D-(-)-PENICILLAMINE
  • D-beta,beta-Dimethylcysteine D-beta-Mercaptovaline
  • H-b,b-DiMethyl-D-Cys-OH, H-b-Mercapto-D-Val-OH
  • D-PenicillamineUSP, 97.0-102.0% (Assay)
  • D-β,β-Dimethylcysteine
  • Mercaptovaline
  • 3-Thio-D-valine
  • D-Penicillamine, (2S)-2-Amino-3-methyl-3-sulphanylbutanoic acid
  • Cuprenil
  • Cuprimin
  • D-3-Mercaptovaline
  • D-beta-Thiovaline
  • Depamine
  • Dimethylcysteine
  • D-Mercaptovaline
  • D-Penamine
  • D-Penicyllamine
  • d-valin
  • D-Valine, 3-mercapto-
  • emtexate
  • Mercaptyl
  • Metalcaptase
  • Pendramine
  • Perdolat
  • D-PENICILLAMINE
  • DISTAMINE
  • 3-MERCAPTO-D-VALINE
  • 3,3-DIMETHYL-D(-)-CYSTEINE
  • 3,3-DIMETHYL-D-CYSTEINE
  • β,β-dimethlcycteine
  • D-PENICILLAMINE, 99+%
  • 3,3-Dimethyl-D-cysteine~3-Mercapto-D-valine
  • D-minus-penicillamine free base
  • Penicilllamine
  • SS,SS-DIMETHLCYCTEINE
  • (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid
  • (S)-3,3-Dimethylcysteine
  • b-Thiovaline
  • Cupripen
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