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(±)-Penicillamine

(±)-Penicillamine structure

CAS No:
52-66-4
Formula:
C5H11NO2S
Chemical Name:
(±)-Penicillamine
Synonyms:
Valine,3-mercapto-;Valine,3-mercapto-,DL-;DL-Valine,3-mercapto-;3-Mercaptovaline;dl-DMC;DL-Penicillamine;DL-β-Mercaptovaline;(±)-Penicillamine;DL-3-Mercaptovaline;β,β-Dimethylcysteine;DMC;β-Mercaptovaline;Cysteine,3,3-dimethyl-;β-Thiovaline;2-Amino-3-mercapto-3-methylbutyric acid;NSC 22880;NSC 44656;2-Azaniumyl-3-methyl-3-sulfanylbutanoate;2-Amino-3-methyl-3-sulfanylbutanoic acid;2-Amino-3-mercapto-3-methylbutanoic acid;5139-02-6
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

white to almost white crystalline powder

Solid

Penicillamine is an alpha-amino acid having the structure of valine substituted at the beta position with a sulfanyl group. It is a non-proteinogenic alpha-amino acid and a thiol.|3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease.

(±)-Penicillamine Basic Attributes

Molecular Weight：

149.208

Exact Mass：

149.21

EC Number：

200-147-2

NSC Number：

81988|241261|44656|22880

DSSTox ID：

DTXSID7044687

HScode：

2930909090

Characteristics

PSA：

64.3

XLogP3：

-1.8

Appearance：

Solid

Density：

1.2±0.1 g/cm3

Melting Point：

201 °C (decomp)

Boiling Point：

251.8±35.0°C at 760 mmHg

Flash Point：

106.1±25.9 °C

Refractive Index：

1.528

Water Solubility：

Soluble in ethanol, hot water and sodium hydroxide.

Storage Conditions：

Packaging and storage: Store below 40 deg C (104 deg F), preferably between 15 and 30 deg C (59 and 86 deg F), unless otherwise specified by manufacturer. Store in a tight container. /Penicillamine tablets USP/

Toxicity：

LD50 orally in rats: 365 mg/kg (Jaffe)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R22

safety instructions：

S26;S36

RTECS Number：

YV9445000

Marks：

Xn:Harmful;

Stability/Shelf Life：

AQ SOLN IS COMPARATIVELY STABLE @ PH 2-4

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)|Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)|Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)

MeSH Entry Terms：

beta,beta Dimethylcysteine

(±)-Penicillamine Use and Manufacturing

antirheumatic, chelating agent (copper), Wilson's desease treatment

Computed Properties

Molecular Weight:149.21
XLogP3:-1.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:149.05104977
Monoisotopic Mass:149.05104977
Topological Polar Surface Area:64.3
Heavy Atom Count:9
Complexity:124
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 52-66-4

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