2-((3-Aminopropyl)amino)ethanethiol
Basic information
- CAS
31098-42-7- Standard SMILES
NCCCNCCS- InChIKey
YHPLKWQJMAYFCN-UHFFFAOYSA-N- Molecular formula
- C5H14N2S
- Average molar mass
- 134.25 g/mol
- Monoisotopic mass
- 134.08776963
Overview
WR-1065 is an alkanethiol that is the N-3-aminopropyl derivative of cysteamine. Used as the S-phosphorylated prodrug, amifostine, for cytoprotection in cancer chemotherapy and radiotherapy. It has a role as an antioxidant, a drug metabolite and a radiation protective agent. It is a diamine and an alkanethiol. It is functionally related to a cysteamine.
Names & identifiers
- Preferred name
- 2-((3-Aminopropyl)amino)ethanethiol
- IUPAC
- 2-(3-aminopropylamino)ethanethiol
- English name
- 2-(3-aminopropylamino)ethanethiol
- Molecular formula
- C5H14N2S
- Molecular weight
- 134.24
Names & synonyms
Amifostine thiol31098-42-72-(3-aminopropylamino)ethanethiol2-((3-Aminopropyl)amino)ethanethiolWR 1065WR-10652-[(3-aminopropyl)amino]ethanethiolNSC-647527Ethanethiol, 2-[(3-aminopropyl)amino]-N-(2-mercaptoethyl)-1,3-diaminopropaneEthanethiol, 2-((3-aminopropyl)amino)-05P3K9I49L
Show more names
Demeton Impurity 5Ethanethiol,2-[(3-aminopropyl)amino]-2-((3-Aminopropyl)amino)ethyl hydrosulfide
WR1065CHEBI:725832-((aminopropyl)amino)ethanediolRefChem:836902-[(3-aminopropyl)amino]ethane-1-thioln-(2-mercaptoethyl)-1,3-propanediamineNSC6475272-((3-aminopropyl)amino)ethane-1-thiol
Database identifiers
- CAS
31098-42-7- PubChem CID
- 104807
- DTXSID
DTXSID90953197- ChEMBL
CHEMBL1201382- ChEBI
CHEBI:72583- UNII
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 39.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 41.4
Physicochemical properties
- Boiling point
- 218.6 · 218.6±15.0 °C(Predicted)
- Density
- 0.975 · 0.975±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light, stored under nitrogen
- solubility
- 1 mg/mL · DMSO: < 1 mg/mL (insoluble or slightly soluble)
- pka
- 10 · 10.00±0.10(Predicted)
- form
- Solid
- color
- White
- Water Solubility
- 250 mg/mL · Water: 250 mg/mL (1862.34 mM)
- FDA UNII
- 5 P3K9I49L · 05P3K9I49L
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 301 · P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- Hazard statements
- H314
- Precautionary statements
- P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationDrugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military.
Applications
UsesAmifostine Thiol is a metabolite of Amifostine (A576810) which provides normal cells with selective protection against the toxic effects of cancer chemotherapy and radiation treatment.
Additional notes
DefinitionChEBI: An alkanethiol that is the N-3-aminopropyl derivative of cysteamine. Used as the S-phosphorylated prodrug, amifostine, for cytoprotection in cancer chemotherapy and radiotherapy.
Related reactions
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Compound notes
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