L-Penicillamine - ≥98%(T) , CAS No.1113-41-3

CAS: 1113-41-3 Cat. No.: S161218 Molecular Weight: 149.21 Beilstein Registry Number: 1722370 EC Number: 214-203-9

GRADE & PURITY ≥98%(T)

Synonyms

P1370 | NCGC00014602-04 | L-(+)-Penicillamine | NCIStruc2_000062 | (R)-2-Amino-3-mercapto-3-methylbutanoicacid | PENICILLAMINE L-FORM [MI] | Pharmakon1600-01500464 | CCRIS 2902 | NCGC00014602 | NCGC00094751-02 | AS-49399 | CCG-36579 | Sch 10649 | (R)-2-Am

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

L-Penicillamine(3,3-Dimethyl-L-cysteine) is good water-soluble compound. It is generally used as a metal-chelating agent.

Application：

L-Penicillamine is used:
In the synthesis of Cu nanoclusters (CuNCs) from copper(II).
In the preparation of ligands based onpyridine-2,6-dicarboxylic acid, which is in combination with cobalt (III) to convert acetonitrile to acetamide and benzonitrile to benzamide.

Specifications

Synonyms

P1370 | NCGC00014602-04 | L-(+)-Penicillamine | NCIStruc2_000062 | (R)-2-Amino-3-mercapto-3-methylbutanoicacid | PENICILLAMINE L-FORM [MI] | Pharmakon1600-01500464 | CCRIS 2902 | NCGC00014602 | NCGC00094751-02 | AS-49399 | CCG-36579 | Sch 10649 | (R)-2-Am

Specifications & Purity

≥98%(T)

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(T)

Names and Identifiers

• Pubchem Sid: 488186733
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186733
• Canonical Smiles: CC(C)(C(C(=O)O)N)S
• IUPAC Name: (2R)-2-amino-3-methyl-3-sulfanylbutanoic acid
• InChIKey: VVNCNSJFMMFHPL-GSVOUGTGSA-N
• INCHI: 1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m1/s1
• Isomeric SMILES: CC(C)([C@@H](C(=O)O)N)S
• WGK Germany: 2
• RTECS: YV9445500
• Molecular Weight: 149.21
• Beilstein: 1722370
• Reaxy-Rn: 1722376
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1722376&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Valine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Valine and derivatives
• Alternative Parents: L-alpha-amino acids Thia fatty acids Methyl-branched fatty acids Amino acids Monocarboxylic acids and derivatives Carboxylic acids Alkylthiols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Valine or derivatives - Alpha-amino acid - L-alpha-amino acid - Branched fatty acid - Methyl-branched fatty acid - Thia fatty acid - Fatty acyl - Fatty acid - Amino acid - Alkylthiol - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Primary aliphatic amine - Organic oxide - Carbonyl group - Organopnictogen compound - Amine - Organic oxygen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as valine and derivatives. These are compounds containing valine or a derivative thereof resulting from reaction of valine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: penicillamine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

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Associated Targets(non-human)

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

dapE Succinyl-diaminopimelate desuccinylase (42 Activities)

Discover Target: dapE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

spt Serine palmitoyltransferase (15 Activities)

Discover Target: spt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: [α]24/D +61.9°, c = 0.5 in 1 M NaOH
• Melt Point(°C): 206 °C
• Molecular Weight: 149.210 g/mol
• XLogP3: -1.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 149.051 Da
• Monoisotopic Mass: 149.051 Da
• Topological Polar Surface Area: 64.300 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 124.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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2. Yarong Gu, Yuchao Du, Wenhe Wang, Xiaosheng Fang, Ziqing Li, Lijuan Zhao.  (2023)  Enantioselective inorganic nanomaterials with near-infrared circular-polarized-activated photothermal response.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.144873]

3. Hongxia Chen, Junyu Chen, Chao Yuan, Long Yu, Mingtai Sun, Dejian Huang, Shaoquan Liu, Suhua Wang.  (2022)  Metal-organic frameworks-based broad-spectrum sensor for total tetracycline antibiotics assay.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2022.110887]

4. Kangling Tang, Yu Chen, Sisi Tang, Xiaodan Wu, Pengfei Zhao, Jinli Fu, Huibin Lei, Zhaoxia Yang, Zhaohui Zhang.  (2022)  A smartphone-assisted down/up-conversion dual-mode ratiometric fluorescence sensor for visual detection of mercury ions and l-penicillamine.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:36179841] [10.1016/j.scitotenv.2022.159073]

5. Jiajia Lian, Pei Liu, Qingyun Liu.  (2022)  Nano-scale minerals in-situ supporting CeO2 nanoparticles for off-on colorimetric detection of L–penicillamine and Cu2+ ion.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:35364537] [10.1016/j.jhazmat.2022.128766]

6. Jun Zhang, Tingyang Xing, Min Zhang, Yunlong Zhou.  (2022)  Facile preparation of Cu2-xS supernanoparticles with an unambiguous SERS enhancement mechanism.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2021.134457]

7. Jinglei Liu, Wenbo Yuan, Caifeng Li, Mengmeng Cheng, Yan Su, Lijian Xu, Tianfei Chu, Shifeng Hou.  (2021)  l-Cysteine-Modified Graphene Oxide-Based Membrane for Chiral Selective Separation.  ACS Applied Materials & Interfaces,      [PMID:34628847] [10.1021/acsami.1c14900]

8. Hai-Bo Wang, Bei-Bei Tao, An-Li Mao, Zhong-Liang Xiao, Yan-Ming Liu.  (2021)  Self-assembled copper nanoclusters structure-dependent fluorescent enhancement for sensitive determination of tetracyclines by the restriction intramolecular motion.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2021.130729]

9. Shutong Yang, Fangling Wu, Fanzhen Yu, Liancheng Gu, Huanhuan Wang, Yiyi Liu, Yanqiu Chu, Fengyan Wang, Xiang Fang, Chuan-Fan Ding.  (2021)  Distinction of chiral penicillamine using metal-ion coupled cyclodextrin complex as chiral selector by trapped ion mobility-mass spectrometry and a structure investigation of the complexes.  ANALYTICA CHIMICA ACTA,      [PMID:34625257] [10.1016/j.aca.2021.339017]

10. Xiao Shao, Tianyong Zhang, Bin Li, Minghao Zhou, Xiaoyuan Ma, Jingchao Wang, Shuang Jiang.  (2019)  Chiroptical Activity of Type II Core/Shell Cu2S/CdSe Nanocrystals.  INORGANIC CHEMISTRY,      [PMID:31007027] [10.1021/acs.inorgchem.9b00769]

11. Jun Zhang, Kai Wu, Xiaoqing Gao, Min Zhang, Xin Zhou, Florian Bertram, Chen Shen, Yunlong Zhou.  (2024)  Achiral and chiral ligands synergistically harness chiral self-assembly of inorganics.  Science Advances,  10  (42):   [PMID:39423258] [10.1126/sciadv.ado5948]

12. Haimei Yang, Zixuan Ding, Jiayin Du, Xianlin He, Jianan Huang.  (2024)  Optical activity invertible chiral WSe2 quantum dots as intracellular redox state indicator and regulator.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.149839]

13. Ting Tao, Yuyu Cao, Liping Zhang, Dayi Xu, Kaiyuan Pang, Yanli Li, Xiaobao Wei, Zengxian Sun.  (2024)  Preparation of thiol-free amino acid plasma matrix for quantification of thiol amino acids and their oxidized forms in human plasma by UPLC-MS/MS.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:38432109] [10.1016/j.chroma.2024.464776]

14. Zhaoxuan Liu, Xuan Kuang, Xu Sun, Yong Zhang, Qin Wei.  (2019)  Electrochemical enantioselective recognition penicillamine isomers based on chiral C-dots/MOF hybrid arrays.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2019.05.033]

15. Kun Yang, Ruyi Wang, Junjian Lu, Jin Wang, Xuewei Liao, Chen Wang.  (2024)  A covalent organic framework nanosheet-nanochannel composite with signal amplification strategy for electrochemical enantioselective recognition.  TALANTA,      [PMID:38823324] [10.1016/j.talanta.2024.126331]

16. Hu Junyi, Dong Zhuoya, Chu Chaoyang, Ma Yanhang.  (2025)  Quantification of enantiomorphs in chiral crystalline powders through three-dimensional electron diffraction.  Nature Chemistry,      [PMID:40993250] [10.1038/s41557-025-01950-5]

17. Haiyan Yao, Yuan Fan, Emine Sumeyra Turali Emre, Jiaolong Wang, Xuewen Wang, Junchao Wei.  (2025)  Penicillamine-based chiral ZnO nanoparticles: A dual mechanism for infected wound healing via antibacterial activity and immune regulation.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.169284]

18. Jingyi Yu, Mei Xiang, Mingqun Li, Sicong Zeng, Jicheng Cai, Zhiqiang Mao, Fan Zhang.  (2026)  Engineering MOF-Assembled Nanochannels for Enantioselective Detection and Separation of Chiral Drugs.  ANALYTICAL CHEMISTRY,      [PMID:41703944] [10.1021/acs.analchem.5c07686]

19. Simin Cheng, Binqian Zhou, Fan Fang, Yunxiang Zhang, Wei Chen, Haodong Tang, Jun Tang, Xiaoqian Xu, Yiwen Li, Jiaji Cheng, Junjie Hao.  (2026)  Chiral Vanadium Oxide Nanostructures for H2O2 Sensing.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.5c05877]