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CAS No 52-67-5 , (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid

  • Name: (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
  • Synonyms: penicillamine; Cuprimine;D-Penicillamine;(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid; Mercaptyl; 3-Mercapto-D-valine; Depen; Mercaptovaline; Cuprenil; Metalcaptase; Artamine;
  • CAS Registry Number:
  • Melting Point: 212 ºC
  • Flash Point: 106.1°C
  • Boiling Point: 251.8°Cat760mmHg
  • Density: 1.204g/cm3
  • Refractive index: -63 ° (C=1, 1mol/L NaOH)
  • Alpha: -65 º (C=5, 1M NAOH, ON DRY)
  • Water Solubility: 11.1 G/100 ML (20 ºC)
  • Safety Statements: 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.
  • Hazard Symbols: Xi,T,Xn
  • HS Code: 29309016
  • Flash Point: 106.1°C
  • EINECS: 200-148-8
  • Molecular Weight: 149.21134
  • InchiKey: VVNCNSJFMMFHPL-VKHMYHEASA-N
  • InChI: InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
  • Risk Statements: S24/25
  • Molecular Formula: C5H11NO2S
  • Molecular Structure:CAS No:52-67-5 (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
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52-67-5 D-Penicillamine, 99%

  • D-Penicillamine, 99%
  • China Pleapharma Co.,Ltd [Manufacturer]
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52-67-5 D-Penicillamine

  • United States Alfa Chem null
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52-67-5 HALOPERIDOL

  • HALOPERIDOL, BP/USP
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  • India Manus Aktteva, India [Manufacturer]
  • Tel: +91 79 30071152/90/53/75/76
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  • Address: 95, Rangwala Towers, Lawgarden, Ellisbridge, 380006 AhmedabadINDIA Ahmedabad,nullIndia
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52-67-5 H-D-Pen-OH

  • H-D-Pen-OH
  • United States Advanced ChemTech [Manufacturer]
  • Tel: 800-456-1403
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  • Address: 5609 Fern Valley Rd40228 LouisvilleUNITED STATES Louisville,nullUnited States
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52-67-5 D-Penicillamine

  • D-Penicillamine, 99%
  • China Tianjin Pharmacn Science Co., Ltd. [Manufacturer]
  • Tel: 86-22-23359620/ 86-13612042162 (mobile)
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  • Address: 1006 Sinochem Building, 707 Lianmeng RD, Shijiazhuang 050061, Hebei, China null,nullChina
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52-67-5 D-PENICILLAMINE

  • Switzerland BIOTREND Chemicals AG [Manufacturer]
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  • Address: BIOTREND Chemicals AG
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52-67-5 D(-)-Penicillamine

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52-67-5 D-PENICILLAMINE

  • Germany BIOTREND Chemikalien GmbH [Manufacturer]
  • Tel: ++49 (0)2 21 9 49 83 20
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  • Address: BIOTREND Chemikalien GmbH
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52-67-5 PENICILLAMINE(D-)

  • United States Richman Chemical, Inc. [Manufacturer]
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  • Address: Richman Chemical, Inc.
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52-67-5 Penicillamine

  • Penicillamine
  • United States LKT Laboratories, Inc [Manufacturer]
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References of (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
Title: Penicillamine
CAS Registry Number: 52-67-5
CAS Name: 3-Mercapto-D-valine
Synonyms: (S)-3,3-dimethylcysteine; a-amino-b-methyl-b-mercaptobutyric acid; DMC; b-thiovaline; D-penicillamine
Trademarks: Cuprimine (Merck & Co.); Cupripen (Rubio); Depen (Wallace Labs.); D-Penamine (Dista); Distamine (Dista); Mercaptyl (Knoll); Metalcaptase (Heyl); Reumacillin (Leiras); Sufortan (Sanfer); Trisorcin (Merckle); Trolovol (Dexo)
Molecular Formula: C5H11NO2S
Molecular Weight: 149.21
Percent Composition: C 40.25%, H 7.43%, N 9.39%, O 21.45%, S 21.49%
Literature References: Characteristic degradation product of penicillin type antibiotics. Active as copper chelating agent and as a disease modifying antirheumatic drug (DMARD). Prepn by hydrolysis of penicillins: E. P. Abraham et al., Nature 151, 107 (1943). Review of syntheses of DL-form and enantiomers: H. M. Crooks in The Chemistry of Penicillin, H. T. Clarke et al., Eds. (Princeton Univ. Press, 1949) pp 455-472; W. M. Weigert et al., Angew. Chem. Int. Ed. 14, 330 (1975). Polymorphism of D-form: J. A. G. Vidler, J. Pharm. Pharmacol. 28, 662 (1976). Toxicity data: Veis et al., Antibiotiki 14, 837 (1969). General reviews: I. A. Jaffe in Pharmacological and Biochemical Properties of Drug Substances Vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 465-478; C. C. Chiu, L. T. Grady, Anal. Profiles Drug Subs. 10, 601-637 (1981). Review of assay methods: N. Kucharczyk, S. Shahiniam, J. Rheumatol. 8, Suppl. 7, 28-34 (1981); of metabolism and pharmacology: D. Perrett, ibid. 41-50; of clinical pharmacokinetics: D. A. Joyce, Pharmacol. Ther. 42, 405-427 (1989). Clinical trial in Wilson's disease: A. Czlonkowska et al., J. Neurol. 243, 269 (1996). Review of clinical experience in rheumatoid arthritis: R. Munro, H. A. Capell, Br. J. Rheumatol. 36, 104-109 (1997).
Properties: White or practically white, crystalline powder. mp 202-206° (Weigert). [a]D25 -63° (c = 0.1 in pyridine). Freely sol in water; slightly sol in alcohol. Insol in ether, acetone, benzene, carbon tetrachloride. LD50 in rats (mg/kg): >10000 orally, >660 i.p. (Jaffe).
Melting point: mp 202-206° (Weigert)
Optical Rotation: [a]D25 -63° (c = 0.1 in pyridine)
Toxicity data: LD50 in rats (mg/kg): >10000 orally, >660 i.p. (Jaffe)
 
Derivative Type: Hydrochloride
CAS Registry Number: 2219-30-9
Trademarks: Pemine (Lilly)
Molecular Formula: C5H11NO2S.HCl
Molecular Weight: 185.67
Percent Composition: C 32.34%, H 6.51%, N 7.54%, O 17.23%, S 17.27%, Cl 19.09%
Properties: Hygroscopic crystals, dec 177.5°. [a]D25 -63° (1N NaOH). Freely sol in water, sol in ethanol. Aq solns are comparatively stable at pH 2-4. LD50 i.v. in mice: 2289 mg/kg (Veis).
Optical Rotation: [a]D25 -63° (1N NaOH)
Toxicity data: LD50 i.v. in mice: 2289 mg/kg (Veis)
 
Derivative Type: DL-Form
CAS Registry Number: 52-66-4
Properties: Crystals, dec 201°. pK: 1.8 (carboxyl); 7.9 (a-amino); 10.5 (b-thiol). LD50 orally in rats: 365 mg/kg (Jaffe).
pKa: pK: 1.8 (carboxyl); 7.9 (a-amino); 10.5 (b-thiol)
Toxicity data: LD50 orally in rats: 365 mg/kg (Jaffe)
 
Derivative Type: DL-Form hydrochloride
CAS Registry Number: 22572-05-0
Properties: Crystals, dec 145-148°.
 
Derivative Type: L-Form
CAS Registry Number: 1113-41-3
Properties: Crystals, mp 190-194°. [a]D25 +63° (in 1N NaOH). LD50 i.p. in rats: 350 mg/kg (Jaffe).
Melting point: mp 190-194°
Optical Rotation: [a]D25 +63° (in 1N NaOH)
Toxicity data: LD50 i.p. in rats: 350 mg/kg (Jaffe)
 
Therap-Cat: Antirheumatic. Chelating agent (copper); Wilson's Disease treatment.
Keywords: Antiarthritic/Antirheumatic; Chelating Agent; Wilson's Disease Treatment.