L-Penicillamine

L-Penicillamine
  • CAS No.:1113-41-3
Other grades of this product :
L-Penicillamine Basic information
Product Name:L-Penicillamine
Synonyms:3-MERCAPTO-L-VALINE;3-THIOL-VALINE;3,3-DIMETHYL-L-CYSTEINE;TIMTEC-BB SBB000102;L-BETA,BETA-DIMETHYLCYSTEINE;L-BETA-MERCAPTOVALINE;L-(+)-PENICILLAMINE;L-PENICILLAMINE
CAS:1113-41-3
MF:C5H11NO2S
MW:149.21
EINECS:214-203-9
Product Categories:Amino Acids & Derivatives;Intermediates & Fine Chemicals;Amino Acids;Biochemistry;non-Proteinorganic Amino Acids;Pharmaceuticals;1
Mol File:1113-41-3.mol
L-Penicillamine Chemical Properties
Melting point 206 °C (dec.)(lit.)
alpha 61.9 º (C=0.5 IN 1 M NAOH)
Boiling point 251.8±35.0 °C(Predicted)
density 1.113 (estimate)
refractive index 63 ° (C=1, 1mol/L NaOH)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Aqueous Base (Sparingly), DMSO (Slightly, Heated), Water (Slightly)
pka2.13±0.12(Predicted)
form Crystalline Powder
color White to almost white
optical activity[α]24/D +61.9°, c = 0.5 in 1 M NaOH
Merck 14,7088
BRN 1722374
Stability:Hygroscopic
InChIKeyVVNCNSJFMMFHPL-GSVOUGTGSA-N
CAS DataBase Reference1113-41-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-40-20/21/22
Safety Statements 26-36-22-24/25
WGK Germany 2
RTECS YV9445500
HS Code 29309090
ToxicityLD50 i.p. in rats: 350 mg/kg (Jaffe)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
L-Penicillamine Usage And Synthesis
Chemical Propertieswhite to almost white crystalline powder
UsesAs a Penicillin metabolite, L-Penicillamine can be used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.
UsesL-Penicillamine is a metabolite of penicillin. L-Penicillamine is used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.
UsesMetal-chelating agent
DefinitionChEBI: The L-enantiomer of penicillamine.
IndicationsPenicillamine (Cuprimine) can be used to treat acute, severe rheumatoid arthritis, producing reductions in joint pain, edema, and stiffness.The response to penicillamine is usually delayed (4–12 weeks), and remissions can last several months after withdrawal of treatment. Radiographic evidence of this drug’s efficacy is limited; thus, penicillamine is seldom used to treat rheumatoid arthritis.
Mechanism of actionThe mechanism of action of penicillamine is unknown, but some evidence suggests that it may involve the inhibition of angiogenesis, synovial fibroblast proliferation, or transcriptional activation. Because penicillamine can chelate copper and promote its excretion, it is used to treat Wilson’s disease (hepatolenticular degeneration) and has also been used in mercury and lead intoxication.
PharmacologyPenicillamine is readily absorbed from the GI tract and is rapidly excreted in the urine, largely as the intact molecule. Gradually increasing its dose minimizes side effects, which necessitate discontinuance of penicillamine therapy in perhaps one-third of patients. The most common side effects are maculopapular pruritic dermatitis, GI upset, loss of taste sensation, mild to occasionally severe thrombocytopenia and leukopenia,and mild proteinuria, which at times may progress to the nephritic syndrome. Discontinuance of therapy usually results in a rapid disappearance of side effects.
Safety ProfileA poison by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx and SOx.
Purification MethodsSame as preceding entry for its enantiomer. [Beilstein 4 IV 3228.]
L-Penicillamine Preparation Products And Raw materials
Preparation ProductsH-BETA,BETA-DIMETHYL-L-CYS(PMEOBZL)-OH

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