D-Penicillamine , >98.0%(T) , 52-67-5

Synonym(s):
D-(−)-2-Amino-3-mercapto-3-methylbutanoic acid;D-Penicillamine;3,3-Dimethyl-D-cysteine;3-Mercapto-D-valine

CAS NO.：52-67-5

Empirical Formula: C5H11NO2S

Molecular Weight: 149.21

MDL number: MFCD00064302

EINECS: 200-148-8

PRODUCT Properties

• Melting point: 210 °C (dec.)(lit.)
• Boiling point: 251.8±35.0 °C(Predicted)
• alpha: -65 º (c=5, 1M NaOH, on dry)
• Density: 1.113 (estimate)
• refractive index: -63 ° (C=1, 1mol/L NaOH)
• storage temp.: 2-8°C
• solubility: H2O: soluble100mg/mL
• pka: pKa 7.83±0.01(H2O,t =37±0.05,I=0.15)(Approximate)
• form: Powder
• color: White to almost white
• optical activity: -6325 (pyridine), L-form: +6325 (1 mol dm-3 NaOH)
• Water Solubility: 11.1 g/100 mL (20 ºC)
• Merck: 14,7088
• BRN: 1722375
• BCS Class: 3
• Stability: Stable. Incompatible with strong oxidizing agents.
• InChIKey: VVNCNSJFMMFHPL-VKHMYHEASA-N

Description and Uses

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.

chelating agent (Cu), antirheumatic

Safety

• Symbol(GHS): GHS08
• Signal word: Warning
• Hazard statements: H361d
• Precautionary statements: P201-P202-P280-P308+P313-P405-P501
• Hazard Codes: Xi,T,Xn
• Risk Statements: 36/37/38-40-20/21/22
• Safety Statements: 26-36-24/25-22
• WGK Germany: 2
• RTECS: YV9425000
• Hazard Note: Toxic
• HS Code: 29309016
• Toxicity: LD50 in rats (mg/kg): >10000 orally, >660 i.p. (Jaffe)