Conditions | Yield |
---|---|
With ammonia at 45℃; under 11251.1 Torr; for 0.666667h; Temperature; Pressure; | 97% |
Conditions | Yield |
---|---|
With ethanol; hydrogen sulfide | |
With hydrogen sulfide unter Kuehlung; |
Conditions | Yield |
---|---|
With hydrogenchloride; water |
2,2'-dithio-bis[ethylamine]
potassium cyanide
A
4,5-Dihydro-thiazol-2-ylamin
B
Cysteamine
S-benzylcysteamine hydrochloride
Cysteamine
Conditions | Yield |
---|---|
With ammonia; sodium |
GLUTATHIONE
2,2'-dithio-bis[ethylamine]
A
(S)-2-Amino-4-[(R)-2-(2-amino-ethyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
B
Cysteamine
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; |
GLUTATHIONE
(S)-2-Amino-4-[(R)-2-(2-amino-ethyldisulfanyl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-butyric acid
A
Oxidized glutathione
B
Cysteamine
Conditions | Yield |
---|---|
With sodium chloride In water-d2 at 25℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With HO3SC6H4SH Equilibrium constant; pH 6.0; | |
With rac-cysteine Equilibrium constant; pH 7.4, further thiols; | |
With water; diothiothreitol |
Conditions | Yield |
---|---|
With sulfuric acid In water for 0.5h; Heating; |
Conditions | Yield |
---|---|
With hydrazine |
Cysteamine
Conditions | Yield |
---|---|
With water; dinitrogen monoxide at 22℃; Equilibrium constant; Irradiation; various pH; |
thiazolidine-2-thione
hydrogenchloride
A
hydrogen sulfide
B
methylammonium carbonate
C
Cysteamine
Conditions | Yield |
---|---|
at 155℃; |
hydrogenchloride
4,5-dihydro-3H-benzo[f][1,4]thiazocine-1,6-dione
A
benzene-1,2-dicarboxylic acid
B
Cysteamine
Cysteamine
Conditions | Yield |
---|---|
With hydrogen bromide | |
With 1,4-dioxane; cobalt sulfide at 175℃; Hydrogenation.unter Druck; |
Cysteamine
Conditions | Yield |
---|---|
With methanol; sodium methylate |
Conditions | Yield |
---|---|
Hydrogenation; |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; buffer reagents; ascorbic acid In water pH=3.6; Kinetics; Further Variations:; pH-values; Reagents; Decomposition; |
S-nitroso-2-aminoethanethiol
Cysteamine
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; sodium hydrogensulfite In phosphate buffer at 25℃; pH=7.4; Kinetics; Further Variations:; concentration; Substitution; |
NAP
S-nitroso-2-aminoethanethiol
A
Cysteamine
B
S-nitroso-N-acetyl-DL-penicillamine
Conditions | Yield |
---|---|
With phosphate buffer; ethylenediaminetetraacetic acid for 0.0833333h; pH=7.4; Equilibrium constant; Further Variations:; Temperatures; |
Conditions | Yield |
---|---|
Stage #1: 2-amino tritylthio ethane With mercury(II) diacetate; acetic acid at 20℃; Stage #2: With sodium tetrahydroborate In water at 20℃; pH=7 - 8; Further stages.; |
Conditions | Yield |
---|---|
In ethanol in cold alcohol with equimolar amts.; |
L-Cysteine
RRRQRRCcystCcystRGY
A
3-(2-amino-ethyldisulfanyl)-L-alanine
B
L-cystine
C
Cysteamine
Conditions | Yield |
---|---|
In water at 20℃; for 24h; Inert atmosphere; |
Conditions | Yield |
---|---|
With sodium borohydrid; triethylamine In N,N-dimethyl-formamide | |
With sodium borohydrid; triethylamine In N,N-dimethyl-formamide | |
With sodium borohydrid; triethylamine In N,N-dimethyl-formamide |
Cysteamine
Conditions | Yield |
---|---|
With sodium hydroxide In chloroform; water | |
With sodium hydroxide In chloroform; water |
Conditions | Yield |
---|---|
In aq. phosphate buffer for 24h; pH=7; |
3-<(2-aminoethyl)dithio>propionic acid
A
Cysteamine
B
3-mercaptopropionic acid
Conditions | Yield |
---|---|
With diothiothreitol In water at 20℃; for 2h; |
Conditions | Yield |
---|---|
With polystyrene-bound diaryl selenoxide In dichloromethane for 1.5h; | 100% |
borohydride exchange resin (Amberlit IRA-400); copper(II) sulfate In methanol for 3h; Ambient temperature; | 98% |
With dihydrogen peroxide In water for 2h; Inert atmosphere; | 97.5% |
Cysteamine
dimethyl N-cyanodithioiminocarbonate
2-(N-cyanoimino)thiazolidine
Conditions | Yield |
---|---|
In ethanol at 90℃; for 2h; | 100% |
In ethanol for 3h; Heating / reflux; | 67.1% |
In ethanol Heating; |
2-(vinyloxy)ethyl isothiocyanate
Cysteamine
N-(2-vinyloxyethyl)-N'-(2-mercaptoethyl)thiourea
Conditions | Yield |
---|---|
100% |
3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal
Cysteamine
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.25h; Ambient temperature; | 100% |
2,3-O-isopropylidene-α,β-D-mannose
Cysteamine
Conditions | Yield |
---|---|
With triethylamine In methanol at 65℃; | 100% |
acetoacetic acid methyl ester
Cysteamine
(Z)-3-(2-Mercapto-ethylamino)-but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
for 24h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
In benzene at 20℃; for 55h; | 100% |
Conditions | Yield |
---|---|
In benzene at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In methanol at 65℃; for 1h; | 100% |
Cysteamine
Conditions | Yield |
---|---|
With hydrogenchloride; Cumene hydroperoxide; tert-butyl (S)-(tetrahydrotellurophen-3-yl)carbamate In dichloromethane; water at 25℃; Flow reactor; | 100% |
Conditions | Yield |
---|---|
With silica gel for 0.0666667h; Microwave irradiation; neat (no solvent); | 99% |
With hydrogenchloride; potassium hydroxide In water for 1h; | 98% |
With pyridine |
pyridine-4-carbonitrile
Cysteamine
2-(pyridin-4-yl)-4,5-dihydrothiazole
Conditions | Yield |
---|---|
With tribromomelamine at 100℃; for 0.05h; Neat (no solvent); | 99% |
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.133333h; | 98% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.05h; chemoselective reaction; | 96% |
In ethanol Heating; |
2-Chlorobenzonitrile
Cysteamine
2-(2-chlorophenyl)-4,5-dihydro-1,3-thiazole
Conditions | Yield |
---|---|
With tribromomelamine at 100℃; for 0.0666667h; Neat (no solvent); | 99% |
In ethanol for 5h; Heating; | 40% |
Ethyl isothiocyanate
2-{2-[4-(3-Fluoro-phenyl)-piperazin-1-yl]-ethoxy}-benzaldehyde
Cysteamine
2-(2-{2-[4-(3-Fluoro-phenyl)-piperazin-1-yl]-ethoxy}-phenyl)-thiazolidine-3-carbothioic acid ethylamide
Conditions | Yield |
---|---|
99% |
Cysteamine
5-phenylfuran-2,3-dione
N-(2-Mercapto-ethyl)-2,4-dioxo-4-phenyl-butyramide
Conditions | Yield |
---|---|
In 1,4-dioxane for 1h; Heating; | 99% |
iodobenzene
carbon monoxide
Cysteamine
A
S-2-(N-benzoylamino)ethyl benzothioathe
Conditions | Yield |
---|---|
With dichlorido[2,2'-(4-methylbenzene-1,2-diyl)bis(4,4-dimethyl-4,5-dihydro-1,3-oxazole)-N,N']palladium(II); potassium carbonate In acetonitrile at 120℃; under 5171.62 Torr; for 3 - 12h; Catalytic behavior; Time; Autoclave; | A 99% B 12% |
acetyl chloride
Cysteamine
1-[(2-aminoethyl)sulfanyl]ethan-1-one hydrochloride
Conditions | Yield |
---|---|
With trifluoroacetic acid at 0 - 20℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine In water at 140℃; under 3000.3 Torr; for 0.166667h; Reagent/catalyst; Temperature; Pressure; | 98.4% |
With dihydrogen peroxide; acetic acid |
Conditions | Yield |
---|---|
With tribromomelamine at 100℃; for 0.05h; Neat (no solvent); | 98% |
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.0833333h; | 96% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.116667h; chemoselective reaction; | 95% |
N-phenylacetoacetamide
Cysteamine
2-(2-Methyl-thiazolidin-2-yl)-N-phenyl-acetamide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 16h; Heating; | 98% |
With toluene-4-sulfonic acid In benzene for 6h; Heating; | 98% |
metronidazole
Cysteamine
4-<(2-aminoethyl)thio>-2-methylimidazole-1-ethanol
Conditions | Yield |
---|---|
With pH 5.0 In water at 37℃; for 120h; | 98% |
With pH 5.0 at 37℃; for 120h; Product distribution; Mechanism; other reaction conditions; |
4-(2-formylbenzyl)-2-phenylnaphtho<1,8-bc>furan-5-one
Cysteamine
4-<2-(1,3-thiazolidin-2-yl)benzyl>-2-phenylnaphtho<1,8-bc>furan-5-one
Conditions | Yield |
---|---|
In benzene for 12h; Heating; N2, dark; | 98% |
Conditions | Yield |
---|---|
With selenium; oxygen; acetonitrile | 98% |
Stage #1: carbon monoxide; Cysteamine With potassium carbonate; sulfur In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 4h; Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; under 760 Torr; for 2h; | 87% |
Boc-L-phenylalaninal
Cysteamine
(2RS,1'S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazolidine
Conditions | Yield |
---|---|
In benzene for 4h; Ambient temperature; | 98% |
In benzene Yield given; |
Cysteamine
3-nitrobenzonitrile
2-(3-nitrophenyl)-4,5-dihydro-1,3-thiazole
Conditions | Yield |
---|---|
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.0333333h; chemoselective reaction; | 98% |
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.1h; | 88% |
With tribromomelamine at 100℃; for 0.0833333h; Neat (no solvent); | 87% |
In ethanol for 5h; Heating; | 63% |
2,3,5,6-di-O-isopropylidene-D-mannofuranose
Cysteamine
Conditions | Yield |
---|---|
In methanol for 48h; Heating; | 98% |
di-tert-butyl dicarbonate
Cysteamine
2-[(tert-butoxycarbonyl)amino]-1-ethanethiol
Conditions | Yield |
---|---|
In tetrahydrofuran; water at 20℃; for 4h; Inert atmosphere; | 98% |
With triethylamine In dichloromethane at 12℃; for 16h; | 79.9% |
With triethylamine In dichloromethane at 12℃; for 16h; | 79.9% |
Cysteamine
(1'R,2'S)-bicyclomycin C(2'),C(3') acetonide
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water Ambient temperature; | 98% |
benzoylacetonatoboron difluoride
Cysteamine
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.5h; | 98% |
Molecular Structure of Cysteamine (60-23-1):
EINECS: 200-463-0
IUPAC Name: 2-Aminoethanethiol
Molecular Formula: C2H7NS
Molecular Weight: 77.148680 g/mol
XLogP3-AA: -0.4
H-Bond Donor: 1
H-Bond Acceptor: 1
Canonical SMILES: C(CS)N
InChI: InChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
InChIKey: UFULAYFCSOUIOV-UHFFFAOYSA-N
Index of Refraction: 1.485
Molar Refractivity: 22.74 cm3
Molar Volume: 79.2 cm3
Surface Tension: 34.8 dyne/cm
Density: 0.973 g/cm3
Flash Point: 34.6 °C
Enthalpy of Vaporization: 37.11 kJ/mol
Boiling Point: 133.6 °C at 760 mmHg
Vapour Pressure: 8.39 mmHg at 25 °C
Melting Point: 95 °C
Water Solubility: 1e+006 mg/L at 25 °C
Storage Temp.: 2-8 °C
1. | pic-esc 50 mg/L | APMBAY Applied Microbiology. 12 (1964),234. | ||
2. | cyt-ham:ovr 1 mmol/L | CALEDQ Cancer Letters (Shannon, Ireland). 5 (1978),199. | ||
3. | dns-ham:fbr 1 mmol/L | CALEDQ Cancer Letters (Shannon, Ireland). 5 (1978),199. | ||
4. | sce-ham:ovr 100 µmol/L | MUREAV Mutation Research. 68 (1979),351. | ||
5. | ipr-rat LD50:232 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 5 (1955),421. | ||
6. | scu-rat LD50:84 mg/kg | OSDIAF Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. 5 (1956),128. | ||
7. | orl-mus LD50:625 mg/kg | JMCMAR Journal of Medicinal Chemistry. 18 (1975),798. | ||
8. | ipr-mus LD50:250 mg/kg | JMCMAR Journal of Medicinal Chemistry. 12 (1969),510. | ||
9. | scu-mus LD50:84 mg/kg | OSDIAF Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. 5 (1956),128. | ||
10. | ivn-mus LD50:190 mg/kg | CHDDAT Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences, Serie D. 262 (1966),206. |
EPA Genetic Toxicology Program.
Safety Information of Cysteamine (60-23-1):
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22: Harmful if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
RIDADR: 3259
WGK Germany: 3
RTECS: KJ0175000
F: 1-3-10-13-34
Poison by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Cysteamine (60-23-1) is white powder, known as Cysteamine [USAN:BAN] ; Mercaptamine [INN] ; (2-Mercaptoethyl)amine ; 1-Amino-2-mercaptoethylamine ; 2-Amino-1-ethanethiol ; 2-Aminoethanethiol ; 2-Aminoethyl mercaptan ; 2-Mercaptoethanamine ; Becaptan ; CCRIS 3083 ; Cisteamina ; Cisteamina [Italian] ; Cystagon ; Cysteamin ; Cysteinamine ; Decarboxycysteine ; HSDB 7353 ; L 1573 ; L-1573 ; Lambraten ; Lambratene ; MEA ; MEA (mercaptan) ; Mercamine ; Mercaptamina ; Mercaptamina [INN-Spanish] ; Mercaptamine ; Mercaptaminum ; Mercaptaminum [INN-Latin] ; Mercaptoethylamine ; NSC 647528 ; Riacon ; Thioethanolamine ; UNII-5UX2SD1KE2 ; WR 347 ; beta-Aminoethanethiol ; beta-Aminoethylthiol ; beta-Mercaptoethylamine ; Ethanethiol, 2-amino- . Cysteamine (60-23-1) is used to form Coenzyme A by combining with pantothenate and adenosine triphosphate in the body. It is also used for treatment of radiation sickness and disorders of cystine excretion.
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