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Basic Information
CAS No.: 56-17-7
Name: Cystamine dihydrochloride
Molecular Structure:
Molecular Structure of 56-17-7 (Cystamine dihydrochloride)
Formula: C4H12N2S2.2HCl
Molecular Weight: 225.207
Synonyms: Ethanamine,2,2'-dithiobis-, dihydrochloride (9CI);Ethylamine, 2,2'-dithiobis-,dihydrochloride (8CI);2,2'-Dithiobis[ethylamine] dihydrochloride;Bis(2-aminoethyl) disulfide dihydrochloride;Cystamine dichlorohydrate;Cystamine dihydrochloride;Cystamine hydrochloride;WR 352;
EINECS: 200-260-7
Density: 1.172 g/cm3
Melting Point: 217-220 °C (dec.)(lit.)
Boiling Point: 264.8 °C at 760 mmHg
Flash Point: 114 °C
Solubility: soluble in water
Appearance: white powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26-36/37/39
PSA: 102.64000
LogP: 3.28980
Synthetic route

C23H26N2O3S

A

56-17-7

cystamine dihydrochioride

B

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

Conditions
ConditionsYield
Stage #1: C23H26N2O3S With hydrogenchloride In ethyl acetate at 60℃; for 4h;
Stage #2: With oxygen In chloroform at 25℃; for 720h; Further stages.;
A n/a
B 99%
156-57-0

2-mercaptoethylamine hydrochloride

56-17-7

cystamine dihydrochioride

Conditions
ConditionsYield
With dimethyl sulfoxide at 90℃; for 6h;98%
With di(benzothiazol-2-yl)disulfide In methanol; chloroform for 2h; Ambient temperature;96.9%
In methanol oxidation;
With dimethyl sulfoxide In water
In dimethyl sulfoxide at 90℃; for 8h;
120-78-5

di(benzothiazol-2-yl)disulfide

156-57-0

2-mercaptoethylamine hydrochloride

A

56-17-7

cystamine dihydrochioride

B

2-(Benzothiazol-2-yldisulfanyl)-ethylamine; hydrochloride

Conditions
ConditionsYield
In ethanol; chloroform Ambient temperature;

(3SR,4SR)-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3.4]octan-1-one hydrochloride

A

56-17-7

cystamine dihydrochioride

B

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

Conditions
ConditionsYield
In chloroform; dimethyl sulfoxide at 45℃; for 6h;A 23 mg
B 52 mg
56-17-7

cystamine dihydrochioride

C23H26N2O7

112042-52-1

N,N'-biscystamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water Ambient temperature;100%
108-30-5

succinic acid anhydride

56-17-7

cystamine dihydrochioride

108725-86-6

N,N'-(3,4-dithia-hexanediyl)-bis-succinamic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; pH=10;100%
With sodium hydroxide In water pH=10;100%
Stage #1: succinic acid anhydride; cystamine dihydrochioride With sodium hydroxide In water at 20℃; pH=7 - ~ 10;
Stage #2: With hydrogenchloride In water Product distribution / selectivity;
90%
Stage #1: cystamine dihydrochioride With sodium hydroxide In water pH=10;
Stage #2: succinic acid anhydride In water at 20℃; for 2h; pH=7 - 10;
Stage #3: With hydrogenchloride In water
90%
56-17-7

cystamine dihydrochioride

1428361-11-8

C40H40N2O12S2

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With pyridine In ethanol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (+)-usnic acid With pyridine In ethanol for 8h; Reflux;
100%
56-17-7

cystamine dihydrochioride

C40H40N2O12S2

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With pyridine In ethanol at 20℃; for 0.5h;
Stage #2: (+)-usnic acid With pyridine In ethanol for 8h; Inert atmosphere; Reflux;
100%
56-17-7

cystamine dihydrochioride

4055-39-4

mitomycin A

93367-29-4

7-N,7'-N'-bis(2-ethyl)mitomycin C disulfide

Conditions
ConditionsYield
With triethylamine In methanol99%
With triethylamine In methanol for 10h; Ambient temperature;99%
With TEA In methanol at 20℃; for 24h;99%
108-55-4

glutaric anhydride,

56-17-7

cystamine dihydrochioride

109477-57-8

N,N'-diglutaroylcystamine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; pH=10;99%
With sodium hydroxide In water pH=10;99%
Stage #1: glutaric anhydride,; cystamine dihydrochioride With sodium hydroxide In water at 20℃; pH=7 - ~ 10;
Stage #2: With hydrogenchloride In water
90%
Stage #1: cystamine dihydrochioride With sodium hydroxide In water pH=10;
Stage #2: glutaric anhydride, In water at 20℃; for 2h; pH=7 - 10;
Stage #3: With hydrogenchloride In water
90%
Raw Materials
156-57-0
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Chemistry

IUPAC Name: 2-(2-Aminoethyldisulfanyl)ethanamine dihydrochloride 
Molecular Formula: C4H14Cl2N2S2
Molecular Weight: 225.22g/mol
EINECS: 200-260-7
Density: 1.172g/cm3
Melting Point: 217-220 °C
Boiling Point: 264.8°C at 760mmHg
Flash Point: 114°C
Solubility: soluble
Chemical Properties: white powder
Freely Rotating Bonds: 7 
Polar Surface Area: 57.08 Å2 
Polarizability: 10-24cm3 
Enthalpy of Vaporization: 50.27 kJ/mol 
Vapour Pressure: 0.00949 mmHg at 25°C
Stability: stable,incompatible with strong oxidizing agents
The chemical synonyms of Cystamine dihydrochloride (56-17-7) are Bis-(2-aminoethyl)disulfide dihydrochloride ; 2,2'-Dithiodi(ethylammonium) dichloride ; 2,2'-Diaminodiethyl disulfide dihydrochloride ; 2,2'-Dithiobis(ethylamine) dihydrochloride ; Decarboxycystine dihydrochloride .Product categories of Cystamine dihydrochloride (56-17-7) are Pharmaceutical Intermediates .The molecular structure of Cystamine dihydrochloride (56-17-7) is .

Uses

It can be used in the synthesis of heparin antagonist body and fructose bisphosphatase .

Toxicity Data With Reference

1.    

scu-rat LDLo:200 mg/kg

    AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.
2.    

ipr-mus LD50:405 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 21 (1971),284.
3.    

scu-cat LDLo:200 mg/kg

    AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.
4.    

scu-gpg LDLo:300 mg/kg

    AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

A poison by subcutaneous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of HCl, SOx, and NOx. See also SULFIDES.
Hazard Codes:  Xn
Xn:  Harmful
Risk Statements:  22-36/37/38
22:  Harmful if swallowed
36/37/38:  Irritating to eyes, respiratory system and skin
Safety Statements:  37/39-26-36/37/39
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37/39:  Wear suitable gloves and eye/face protection
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection