153881-28-8

Basic information

• Product Name: (3R)-6,8-bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-7-(2-aminoethyl)-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid (non-preferred name)
• CAS NO: 153881-28-8
• Molecular Formula: C₁₇H₂₄N₄O₇S₃
• Molecular Weight: 492.5901
• Mol File: 153881-28-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 747.6°C at 760 mmHg
• Flash Point: 405.9°C
• Density: 1.69g/cm³
• Vapor Pressure: 1.78E-23mmHg at 25°C
• Refractive Index: 1.766
• CAS DataBase Reference: (3R)-6,8-bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-7-(2-aminoethyl)-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-6,8-bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-7-(2-aminoethyl)-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid (non-preferred name)(153881-28-8)
• EPA Substance Registry System: (3R)-6,8-bis{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-7-(2-aminoethyl)-5-hydroxy-3,4-dihydro-2H-1,4-benzothiazine-3-carboxylic acid (non-preferred name)(153881-28-8)

Safety Data

• Hazardous Substances Data: 153881-28-8(Hazardous Substances Data)

Upstream product

• 52-90-4 L-Cysteine 
• 153881-26-6 6-S-cysteinyl-7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid 
• 62-31-7 dopamine hydrochloride 

Relevant articles and documents

Further insights into the influence of L-cysteine on the oxidation chemistry of dopamine: Reaction pathways of potential relevance to Parkinson's disease

The initial step in the genesis of neuromelanin, a black polymeric pigment normally found in the cytoplasm of dopaminergic cell bodies in the substantia nigra (SN), is the autoxidation of dopamine (DA) to DA-o-quninone (1). In this investigation, it is demonstrated that in the presence of L-cysteine (CySH) o-quinone 1 is scavenged to give 5-S-cysteinyldopamine (5-S-CyS-DA, major product) and 2-S-cysteinyldopamine (2-S-CyS-DA, minor product). These cysteinyl conjugates are more easily oxidized than DA. The relative yields of the resulting products are dependent on the concentration of free CySH. These products include 2,5-bi-S-cysteinyldopamine (2,5-bi-S-CyS-DA) and 2,5,6-tri- S-cysteinyldopamine (2,5,6-tri-S-CyS-DA), 7-(2-aminoethyl)-3,4-dihydro-5- hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (DHBT-1), 8-(2-aminoethyl)- 3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (DHBT-5), and a number of cysteinyl conjugates of these dihydrobenzothiazines (DHBTs). 2,5- Bi-S-CyS-DA, DHBT-1, the 6-S-cysteinyl conjugate of DHBT-1, DHBT-5, and the 6-S-cysteinyl conjugate of DHBT-5 were lethal when administered into the brains of laboratory mice and evoke a very characteristic hyperactivity syndrome and episodes of sever tremor. These and related results provide support for the hypothesis that the massive, irreversible loss of glutathione (GSH), increased 5-S-CyS-DA/DA concentration ratio, and depigmentation of dopaminergic neurons in the SN that all occur in Parkinson's disease (PD) might be caused by the γ-glutamyl transpeptidase-mediated translocation of CySH (and/or GSH) into these cells. Furthermore, the resulting cysteinyldopamines and DHBTs might include endotoxic metabolites responsible for the selective degeneration of nigrostriatal dopaminergic neurons and PD.