Cysteine methyl ester

Cysteine methyl ester
Clinical data
Other names	Methyl L-cysteinate
AHFS/Drugs.com	International Drug Names
Identifiers
	IUPAC name methyl (2R)-2-amino-3-sulfanylpropanoate;
CAS Number	2485-62-3 ;
PubChem CID	29145;
ChemSpider	27113 ;
UNII	RQ6L463N3B;
KEGG	D08164 ;
ChEBI	CHEBI:41531;
ChEMBL	ChEMBL1231844;
CompTox Dashboard (EPA)	DTXSID8048365 ;
ECHA InfoCard	100.017.842
Chemical and physical data
Formula	C4H9NO2S
Molar mass	135.18 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC(=O)C(CS)N;
	InChI InChI=1S/C4H9NO2S/c1-7-4(6)3(5)2-8/h3,8H,2,5H2,1H3/t3-/m0/s1 ; Key:MCYHPZGUONZRGO-VKHMYHEASA-N ;

Cysteine methyl ester is the organic compound with the formula HSCH₂CH(NH₂)CO₂CH₃. A white solid, it is the methyl ester of the amino acid cysteine.

Uses

Under the brand name Mecysteine, cysteine methyl ester is a commercial drug with mucolytic activity.[1] It is used as mucolytic and fluidifying for chronic and acute respiratory disorders. The drug is sold under the commercial names Delta in Paraguay, and Pectite and Zeotin in Japan.[2]

Cysteine methyl ester is also used as a building block for synthesis of N,S-heterocycles.[3][4]

References

Page CP (2018). "Respiratory System: Mucolytics". In Datta ST, Xiu P (eds.). Pharmacology (Fifth ed.). Philadelphia, PA. p. 40. ISBN 978-0-7020-7345-8.{{cite book}}: CS1 maint: location missing publisher (link)
"Mecysteine". Drugs.com.
Tanaka, Takashi; Nakashima, Tatsuya; Ueda, Toshihisa; Tomii, Kenji; Kouno, Isao (2007). "Facile Discrimination of Aldose Enantiomers by Reversed-Phase HPLC". Chemical and Pharmaceutical Bulletin. 55 (6): 899–901. doi:10.1248/cpb.55.899. PMID 17541189.
Hamada, Yasumasa; Shibata, Makoto; Sugiura, Tsuneyuki; Kato, Shinji; Shioiri, Takayuki (1987). "New methods and reagents in organic synthesis. 67. A general synthesis of derivatives of optically pure 2-(1-aminoalkyl)thiazole-4-carboxylic acids". The Journal of Organic Chemistry. 52 (7): 1252–1255. doi:10.1021/jo00383a014.

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[1] Page CP (2018). "Respiratory System: Mucolytics". In Datta ST, Xiu P (eds.). Pharmacology (Fifth ed.). Philadelphia, PA. p. 40. ISBN 978-0-7020-7345-8.{{cite book}}: CS1 maint: location missing publisher (link)

[2] "Mecysteine". Drugs.com.

[3] Tanaka, Takashi; Nakashima, Tatsuya; Ueda, Toshihisa; Tomii, Kenji; Kouno, Isao (2007). "Facile Discrimination of Aldose Enantiomers by Reversed-Phase HPLC". Chemical and Pharmaceutical Bulletin. 55 (6): 899–901. doi:10.1248/cpb.55.899. PMID 17541189.

[4] Hamada, Yasumasa; Shibata, Makoto; Sugiura, Tsuneyuki; Kato, Shinji; Shioiri, Takayuki (1987). "New methods and reagents in organic synthesis. 67. A general synthesis of derivatives of optically pure 2-(1-aminoalkyl)thiazole-4-carboxylic acids". The Journal of Organic Chemistry. 52 (7): 1252–1255. doi:10.1021/jo00383a014.