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)

pka

2.13±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

InChIKey

VVNCNSJFMMFHPL-GSVOUGTGSA-N

CAS DataBase Reference

1113-41-3(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

Toxicity

LD50 i.p. in rats: 350 mg/kg (Jaffe)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

L-Penicillamine Usage And Synthesis

Chemical Properties

white to almost white crystalline powder

Uses

L-Penicillamine is a metabolite of penicillin. L-Penicillamine is used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

Uses

Metal-chelating agent

Uses

As a Penicillin metabolite, L-Penicillamine can be used in the treatment of Wilson’s disease, Cystinuria, Scleroderma and arsenic poisoning.

Indications

Penicillamine (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.

Definition

ChEBI: The L-enantiomer of penicillamine.

Mechanism of action

The 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.

Pharmacology

Penicillamine 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 Profile

A poison by intraperitoneal route. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx and SOx.

Purification Methods

Same as preceding entry for its enantiomer. [Beilstein 4 IV 3228.]

L-Penicillamine(1113-41-3)Related Product Information

• L-Valine
• POTASSIUM THIOGLYCOLATE
• Mercaptoacetic acid
• 2-Ethylhexyl mercaptoacetate
• 6-Mercaptopurine
• 3-Mercaptopropionic acid
• Calcium thioglycolate
• (1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
• Sodium thioglycolate
• 3-mercapto-L-valine hydrochloride
• 3-(4-acetylphenyl)-2-aminopropanoic acid hydrochloride
• 3-METHOXY-L-PHENYLALANINE
• (S)-2-AMino-3-(3-iodophenyl)propanoic acid
• 3-Methylphenyl-L-alanine
• L-3-Chlorophenylalanine
• L-3-Cyanophenylalanine
• 2-Chloro-L-phenylalanine
• L-2-Bromophenylalanine