CAS 1113-41-3 (+-)-Penicillamine (HCID 4727)

Names & identifiers

Preferred name: (+-)-Penicillamine
IUPAC: 2-amino-3-methyl-3-sulfanylbutanoic acid
English name: L-Penicillamine
Molecular formula: C5H11NO2S
Molecular weight: 149.21

Names & synonyms

DL-Penicillamine52-66-4(+-)-PenicillamineValine, 3-mercapto-2XOP7Y1H98RefChem:10490432-Amino-3-mercapto-3-methylbutanoic acid3-SulfanylvalineDL-beta-Mercaptovalinebeta-Mercaptovaline2-amino-3-methyl-3-sulfanylbutanoic acid3,3-Dimethyl-DL-cysteine

Show more names

H-PEN-OHl-valinL-Pen-OH3-MERCAPTO-L-VALINE3,3-DIMETHYL-L-CYSTEINE(2R)-2-amino-3-methyl-3-sulfanylbutanoic acidL-(+)-B2NSC 2412613-Mercapto-3-THIOL-VALINE

2-Amino-3-mercapto-3-methylbutyric acid3-MercaptovalineMFCD00004856(+/-)-penicillaminebeta-ThiovalineD-PenicyllamineDL-Valine, 3-mercapto-2-amino-3-methyl-3-sulfanyl-butanoic acid

Database identifiers

CAS: 1113-41-3、25526-04-9、52-66-4、52-67-5
PubChem CID: 4727
DTXSID: DTXSID7044687
ChEMBL: CHEMBL13239
ChEBI: CHEBI:50868
UNII: 2XOP7Y1H98
EC Number: 200-147-2
Nikkaji: J60.801G

Properties

Computed structural properties

XLogP: -1.8
Topological polar surface area: 64.3 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 9
Formal charge: 0
Complexity: 124

Experimental & physicochemical properties

LogP-1.9

Solubility4.65e+00 g/L

Melting Point198.5 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 206 °C · 206 °C (dec.)(lit.)
alpha: 61.9 · 61.9 º (C=0.5 IN 1 M NAOH)
Boiling point: 251.8 · 251.8±35.0 °C(Predicted)
Density: 1.113 · 1.113 (estimate)
refractive index: 63 ° · 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 · 2.13±0.12(Predicted)
form: Crystalline Powder
color: White to almost white
optical activity: 24 · [α]24/D +61.9°, c = 0.5 in 1 M NaOH
Merck: 14 · 14,7088
BRN: 1722374 · 1722374
Stability: Hygroscopic
Major Application: peptide synthesis
InChI: 1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m1/s1
InChIKey: VVNCNSJFMMFHPL-GSVOUGTGSA-N
SMILES: CC(C)(S)[C@H](N)C(O)=O
CAS DataBase Reference: 1113 · 1113-41-3(CAS DataBase Reference)
FDA UNII: 1 YIB7OIG · NO1YIB7OIG
UNSPSC Code: 12352116 · 12352116
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Danger
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 280 h-P305+P351+P338 · P280h-P305+P351+P338
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-40-20/21/22
Safety Statements: 26 · 26-36-22-24/25
WGK Germany: 2 · 2
RTECS: 9445500 · YV9445500
HS Code: 29309090 · 29309090
Storage Class: 11 · 11 - Combustible Solids
Toxicity: 50 i.p · LD50 i.p. in rats: 350 mg/kg (Jaffe)

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Skin Irrit. 2 (100%)；Eye Irrit. 2 (100%)；STOT SE 3 (97.7%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 2
rtecs: YV9445500
hs_code: 29309090
Toxicity: LD50 i.p. in rats: 350 mg/kg (Jaffe)
risk_code: 36/37/38-40-20/21/22
Signal word: Danger
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 26-36-22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P280h-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Applications · 3 items

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

UsesMetal-chelating agent

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