Home Amines 1113-41-3
1113-41-3,MFCD00064303
Catalog No.:AA003516

1113-41-3 | L-Penicillamine

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100mg
95%
in stock  
$17.00   $12.00
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250mg
95%
in stock  
$26.00   $18.00
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1g
95%
in stock  
$62.00   $43.00
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5g
95%
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$190.00   $133.00
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25g
≥ 99% (Assay)
in stock  
$726.00   $508.00
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100g
≥ 99% (Assay)
in stock  
$2,574.00   $1,802.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003516
Chemical Name:
L-Penicillamine
CAS Number:
1113-41-3
Molecular Formula:
C5H11NO2S
Molecular Weight:
149.2113
MDL Number:
MFCD00064303
SMILES:
N[C@@H](C(S)(C)C)C(=O)O
NSC Number:
757265
Properties
Properties
 
BP:
251.8°C at 760 mmHg  
Form:
Solid  
MP:
206 °C (dec.)(lit.)  
Refractive Index:
63 ° (C=1, 1mol/L NaOH)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
124  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
-1.8  

Downstream Synthesis Route

[1]Locationinpatent:experimentalpartOrrling,KristinaM.;Marzahn,MelissaR.;Gutierrez-de-Teran,Hugo;Aqvist,Johan;Dunn,BenM.;Larhed,Mats[BioorganicandMedicinalChemistry,2009,vol.17,#16,p.5933-5949]

[2]Nagasawa;Goon;Muldoon;Zera[JournalofMedicinalChemistry,1984,vol.27,#5,p.591-596]

[3]CurrentPatentAssignee:PERRIGOCOMPANYPUBLICLIMITEDCOMPANY-US2006/13799,2006,A1Locationinpatent:Page/Pagecolumn55

[4]CurrentPatentAssignee:PERRIGOCOMPANYPUBLICLIMITEDCOMPANY-WO2006/127584,2006,A1Locationinpatent:Page/Pagecolumn60;75-77

[5]CurrentPatentAssignee:BIOGENIDECINC.-WO2007/8563,2007,A2Locationinpatent:Page/Pagecolumn80-81

[6]Cook;Heilbron[ChemistryofPenicillin]Werner;Wettstein;Miescher[HelveticaChimicaActa,1947,vol.30,p.432,437]

[7]Mimoto,Tsutomu;Kato,Ryohei;Takaku,Haruo;Nojima,Satoshi;Terashima,Keisuke;Misawa,Satoru;Fukazawa,Tominaga;Ueno,Takamasa;Sato,Hideharu;Shintani,Makoto;Kiso,Yoshiaki;Hayashi,Hideya[JournalofMedicinalChemistry,1999,vol.42,#10,p.1789-1802]

[1]Buchanan,Iain;Garner,C.David;Clegg,William[JournaloftheChemicalSociety,DaltonTransactions,1984,p.1333-1342]

[2]CurrentPatentAssignee:Chvapil,Milos-US2005/80132,2005,A1Locationinpatent:Page/Pagecolumn5

[1]Samanen,J.;Narindray,D.;Cash,T.;Brandeis,E.;Adams,W.;etal.[JournalofMedicinalChemistry,1989,vol.32,#2,p.466-472]

[1]DiMaio,John;Jaramillo,Jorge;Wernic,Dominik;Grenier,Louis;Welchner,Ewald;Adams,Julian[JournalofMedicinalChemistry,1990,vol.33,#2,p.661-667]

[1]Moynihan,HumphreyA.;Roberts,StanleyM.[JournaloftheChemicalSociety.PerkintransactionsI,1994,#7,p.797-806]

Literature

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Separation and determination of chiral composition in penicillamine tablets by capillary electrophoresis in a broad pH range.

Journal: Electrophoresis 20120701

Title: Peroxynitrite has potent pulmonary vasodilator activity in the rat.

Journal: Canadian journal of physiology and pharmacology 20120401

Title: Metal chaperones: a holistic approach to the treatment of Alzheimer's disease.

Journal: Frontiers in psychiatry 20120101

Title: Application of an unusual ninhydrin-based reaction for the indirect chiral resolution of D,L-penicillamine.

Journal: Talanta 20110930

Title: Rational creation of chiral multinuclear and metallosupramolecular compounds from thiol-containing amino acids.

Journal: Dalton transactions (Cambridge, England : 2003) 20110728

Title: Microalbuminuria in rheumatoid arthritis in the post penicillamine/gold era: association with hypertension, but not therapy or inflammation.

Journal: Clinical rheumatology 20110401

Title: Molecular hydrogen protects chondrocytes from oxidative stress and indirectly alters gene expressions through reducing peroxynitrite derived from nitric oxide.

Journal: Medical gas research 20110101

Title: Penicillamine neurotoxicity: an hypothesis.

Journal: ISRN neurology 20110101

Title: Synthesis and biological activity of oxytocin analogues containing unnatural amino acids in position 9: structure activity study.

Journal: Amino acids 20100501

Title: Isolation and quantitative analysis of peroxynitrite scavengers from Artemisia princeps var. orientalis.

Journal: Archives of pharmacal research 20100501

Title: Inhibitors of bacterial N-succinyl-L,L-diaminopimelic acid desuccinylase (DapE) and demonstration of in vitro antimicrobial activity.

Journal: Bioorganic & medicinal chemistry letters 20091115

Title: Cadmium(II) complex formation with cysteine and penicillamine.

Journal: Inorganic chemistry 20090706

Title: A multinuclear coordination system of L-cysteine and L-penicillamine that induce opposite chiralities at metal centers.

Journal: Angewandte Chemie (International ed. in English) 20090101

Title: [Wilson's disease in paediatric age: diagnosis and treatment. Recent advances].

Journal: Recenti progressi in medicina 20081101

Title: Enantiomeric reversed-phase high-performance liquid chromatography resolution of D-/L-penicillamine after spirocyclization with ninhydrin and by using copper(II)-L-proline complex as a chiral selector in the mobile phase.

Journal: Journal of chromatography. A 20080926

Title: Chiral functionalization of optically inactive monolayer-protected silver nanoclusters by chiral ligand-exchange reactions.

Journal: Langmuir : the ACS journal of surfaces and colloids 20080318

Title: Withdrawal of penicillamine from zinc sulphate-penicillamine maintenance therapy in Wilson's disease: promising, safe and cheap.

Journal: Journal of the neurological sciences 20080115

Title: Chiral highly luminescent CdS quantum dots.

Journal: Chemical communications (Cambridge, England) 20071014

Title: Indirect resolution of enantiomers of penicillamine by TLC and HPLC using Marfey's reagent and its variants.

Journal: Biomedical chromatography : BMC 20071001

Title: Peroxynitrite-mediated oxidative damage to brain mitochondria: Protective effects of peroxynitrite scavengers.

Journal: Journal of neuroscience research 20070801

Title: One-electron reduction of S-nitrosothiols in aqueous medium.

Journal: Free radical biology & medicine 20061015

Title: Electrochemical behavior of dopamine at a penicillamine self-assembled gold electrode and its analytical application.

Journal: Archiv der Pharmazie 20060701

Title: Antimelanoma activity of apoptogenic carbonyl scavengers.

Journal: The Journal of pharmacology and experimental therapeutics 20060201

Title: A pilot trial testing the feasibility of administering D-penicillamine to extremely low birth weight neonates.

Journal: Journal of perinatology : official journal of the California Perinatal Association 20060201

Title: Large optical activity of gold nanocluster enantiomers induced by a pair of optically active penicillamines.

Journal: Journal of the American Chemical Society 20051109

Title: Design of high affinity cyclic pentapeptide ligands for kappa-opioid receptors.

Journal: The journal of peptide research : official journal of the American Peptide Society 20051101

Title: Electrochemical determination of thiols at single-wall carbon nanotubes and PQQ modified electrodes.

Journal: Frontiers in bioscience : a journal and virtual library 20050101

Title: N-Salicylideneamino acidato complexes of oxovanadium(IV). The cysteine and penicillamine complexes.

Journal: Dalton transactions (Cambridge, England : 2003) 20040921

Title: Effects of nitric oxide on morphology of isolated cochlear outer hair cells: possible involvement in sensorineural hearing loss.

Journal: Otology & neurotology : official publication of the American Otological Society, American Neurotology Society [and] European Academy of Otology and Neurotology 20030701

Title: Design and synthesis of some substituted 1H-pyrazolyl-oxazolidines or 1H-pyrazolyl-thiazolidines as anti-inflammatory-antimicrobial agents.

Journal: Archiv der Pharmazie 20030401

Title: Electrocatalytic oxidation of nitric oxide at indium hexacyanoferrate film-modified electrodes.

Journal: Analytical and bioanalytical chemistry 20030101

Title: Docking studies reveal a selective binding of D-penicillamine to the transactivator protein of human immunodeficiency virus type 1.

Journal: FEBS letters 20020410

Title: Identification of alpha-dicarbonyl scavengers for cellular protection against carbonyl stress.

Journal: Biochemical pharmacology 20020201

Title: Electrochemical response of dopamine at a penicillamine self-assembled gold electrode.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20011101

Title: Specific sensitization of Lyt-1+2- T cells to spleen cells modified by the drug D-penicillamine or a stereoisomer.

Journal: Journal of immunology (Baltimore, Md. : 1950) 19860101

Title: Studies on the mechanism of the formation of the penicillin antigen. I. Delayed allergic cross-reactions among penicillin G and its degradation products.

Journal: The Journal of experimental medicine 19601130

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Tags:1113-41-3 Molecular Formula|1113-41-3 MDL|1113-41-3 SMILES|1113-41-3 L-Penicillamine