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Merck
CN

76400

D-Penicillamine

≥99.0% (NT)

Synonym(s):

3,3-Dimethyl-D-cysteine, 3-Mercapto-D-valine, D-(−)-2-Amino-3-mercapto-3-methylbutanoic acid

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About This Item

Linear Formula:
(CH3)2C(SH)CH(NH2)CO2H
CAS Number:
52-67-5
Molecular Weight:
149.21
EC Number:
200-148-8
UNSPSC Code:
51101500
PubChem Substance ID:
24886985
Beilstein/REAXYS Number:
1722375
MDL number:
MFCD00064302

Key Documents

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assay

≥99.0% (NT)

optical activity

[α]20/D −63±2°, c = 1% in 1 M NaOH

ign. residue

≤0.05%

mp

210 °C (dec.) (lit.), 214-217 °C (dec.)

mode of action

cell wall synthesis | interferes

SMILES string

CC(C)(S)[C@@H](N)C(O)=O

InChI

1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

InChI key

VVNCNSJFMMFHPL-VKHMYHEASA-N

Gene Information

mouse ... Oprk1(18387)

General description

Chemical structure: β-lactam

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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R John Aitken et al.
Biology of reproduction, 87(5), 110-110 (2012-08-31)
The prolonged incubation of human spermatozoa in vitro was found to induce a loss of motility associated with the activation of mitochondrial reactive oxygen species generation in the absence of any change in mitochondrial membrane potential. The increase in mitochondrial
Maria A Saracino et al.
Talanta, 103, 355-360 (2012-12-04)
D-penicillamine is a thiol drug mainly used for Wilson's disease, rheumatoid arthritis and cystinuria. Adverse effects during normal use of the drug are frequent and may include skin lesions. To evaluate its toxic effects in clinical cases an original method
Thomas Quéméneur et al.
Medicine, 92(1), 1-9 (2012-12-25)
Although the presence of antineutrophil cytoplasmic antibodies (ANCA) has been reported in patients with systemic sclerosis (SSc), the association of SSc and systemic vasculitis has rarely been described. We obtained information on cases of systemic vasculitis associated with SSc in
Xuan Yang et al.
Chemical communications (Cambridge, England), 49(23), 2302-2304 (2013-02-12)
A facile synthesis of chiral penicillamine protected Au nanoclusters with different optical properties has been reported. We have for the first time observed the reversal of CD signals after the scaffolds adsorbed onto the surface of Au NCs. Such Au
Samanta M March et al.
Psychopharmacology, 226(3), 491-499 (2012-12-01)
Animal studies indicate that central acetaldehyde, dependent on catalase metabolism of ethanol (EtOH), modulates ethanol reinforcement. Brain catalase activity and acetaldehyde (ACD) production are significantly higher in rat pups compare d with adults. Interestingly, infant rats show high EtOH affinity
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