Cysteamine (CED0003160)

Record Information
Version1.0
Creation Date2016-05-22 03:39:29 UTC
Update Date2026-05-14 16:50:37 UTC
Accession NumberCHEM016652
Identification
Common NameCysteamine
ClassSmall Molecule
Description
Cysteamine is an organosulfur compound with the formula C2H7NS and an average molecular weight of 77.15 g/mol. Cysteamine belongs to the alkylthiols, a subclass of thiols within the organic compounds. In industrial applications, it is utilized for hair straightening or hair waving. The compound is found in or released from seven recorded sources, including building and construction materials such as tents, canopies, or roofs. It is also associated with electrical and electronic equipment, specifically antennas, amplifiers, and adjustable resistors, as well as healthcare, veterinary, and pharmaceutical products, including ophthalmologicals and alimentary tract and metabolism products. Recorded exposure routes for the substance include oral and ophthalmic pathways. Regarding its biological activity, cysteamine has two recorded protein targets, acting as a binder or unknown interactor of Somatostatin (SST) and Neuropeptide Y receptor type 2 (NPY2R).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-1-ethanethiolChEBI
2-AMINO-ethanethiolChEBI
2-AminoethanethiolChEBI
beta-AminoethanethiolChEBI
beta-AminoethylthiolChEBI
beta-MEAChEBI
beta-MercaptoethylamineChEBI
MEAChEBI
MercaptaminaChEBI
MercaptamineChEBI
MercaptaminumChEBI
ThioethanolamineChEBI
b-AminoethanethiolGenerator
Β-aminoethanethiolGenerator
b-AminoethylthiolGenerator
Β-aminoethylthiolGenerator
b-MEAGenerator
Β-meaGenerator
b-MercaptoethylamineGenerator
Β-mercaptoethylamineGenerator
(2-Mercaptoethyl)amineHMDB
2-Aminoethyl mercaptanHMDB
2-MercaptoethanamineHMDB
Aminoethyl mercaptanHMDB
BecaptanHMDB
CASHHMDB
CisteaminaHMDB
CysteamideHMDB
CysteaminHMDB
CysteaminiumHMDB
CysteinamineHMDB
DecarboxycysteineHMDB
EthanethiolamineHMDB
LambratenHMDB
LambrateneHMDB
MecramineHMDB
MercaminHMDB
MercamineHMDB
MercaptaminHMDB
MerkaminHMDB
RiaconHMDB
35S-Labeled cysteamineHMDB
CystagonHMDB
Cysteamine hydrobromideHMDB
Hydrochloride, cysteamineHMDB
Tosylate, cysteamineHMDB
Cysteamine dihydrochlorideHMDB
Cysteamine hydrochlorideHMDB
Cysteamine maleate (1:1)HMDB
Cysteamine tosylateHMDB
MercaptoethylamineHMDB
2 AminoethanethiolHMDB
Cysteamine bitartrateHMDB
Cysteamine tartrateHMDB
Cysteamine tartrate (1:1)HMDB
Hydrobromide, cysteamineHMDB
Tartrate, cysteamineHMDB
beta MercaptoethylamineHMDB
Bitartrate, cysteamineHMDB
Cysteamine, 35S labeledHMDB
Cysteamine, 35S-labeledHMDB
Dihydrochloride, cysteamineHMDB
Chemical FormulaC2H7NS
Average Molecular Mass77.149 g/mol
Monoisotopic Mass77.030 g/mol
CAS Registry Number60-23-1
IUPAC Name2-aminoethane-1-thiol
Traditional Namecysteamine
SMILESNCCS
InChI IdentifierInChI=1S/C2H7NS/c3-1-2-4/h4H,1-3H2
InChI KeyUFULAYFCSOUIOV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkylthiols. These are organic compounds containing the thiol functional group linked to an alkyl chain.
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassThiols
Sub ClassAlkylthiols
Direct ParentAlkylthiols
Alternative Parents
Substituents
  • Alkylthiol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.5 g/LALOGPS
logP0.01ALOGPS
logP-0.42ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)10.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.39 m³·mol⁻¹ChemAxon
Polarizability8.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-00di-1900000000-287334efed4c27d47e62Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-e26f666cab18d523e475Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-7900000000-25e27a3413a3e9bd6e86Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00dr-3900000000-5f3c0dc6b99382c852e2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-287334efed4c27d47e62Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-1900000000-e26f666cab18d523e475Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-7900000000-25e27a3413a3e9bd6e86Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00dr-3900000000-5f3c0dc6b99382c852e2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00dr-3900000000-5f3c0dc6b99382c852e2Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-2900000000-ba8ae281d3d77ff202c1Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-003u-9000000000-48a76c3cb5971165dc16Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-0fdf5bdcf8a4a1bf9afbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-f99f2f10c6728595d6eaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01t9-9000000000-fa7f96e00debe1bebf70Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9000000000-f7ecadf4e8c1d670f5a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-9bcb6f0736d473b67041Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-9000000000-2607b3d0e4b061c850bdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-1455192f11f88cd089c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-e7f199c21a894c5cf75cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-9000000000-148162e343b3a9f7373bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-9000000000-205aabf68c202f080d99Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9000000000-b167802490bdc502828dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-9000000000-006d44449441398ce13bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-057i-9000000000-b2c213fcf6e17049140bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-ff9c437be9955d96c16eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-ff9c437be9955d96c16eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-947d309fccf2ffba996fNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
236.0Log mg/kg[130:420]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
272Alimentary tract and metabolism productsHealthcare, pharmaceuticals & veterinary productsNot Available
405OphthalmologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
4 pathways
Pantothenate and CoA Biosynthesis
Pantothenate and CoA Biosynthesis
Taurine and Hypotaurine Metabolism
Taurine and Hypotaurine Metabolism
Cysteamine Drug Metabolism
Cysteamine Drug Metabolism
Cysteamine Drug Metabolism Action Pathway
Cysteamine Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSpermine synthaseQ3SZA5Bos taurusPredicted (SEA)0.311397
Click to view 3D structureMitochondrial 2-oxodicarboxylate carrierQ8BZ09Mus musculusPredicted (SEA)0.311397
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)1396.85
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)2256.62
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)1323.2
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)1706.3
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)9.73115
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)1528.57
Click to view 3D structureLeucine aminopeptidaseQ29571Sus scrofaPredicted (SEA)1.79053
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)2768.4
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)4427.44
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)2285.26
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)2992.21
Click to view 3D structureAminopeptidase NP15145Sus scrofaPredicted (SEA)1532.31
Click to view 3D structureDeoxyhypusine synthaseQ9GSW0Plasmodium falciparumPredicted (SEA)56.5964
Click to view 3D structureOrnithine decarboxylaseP09057Rattus norvegicusPredicted (SEA)0.233548
Click to view 3D structurePutative agmatine deiminaseQ8DW17Streptococcus mutans serotype c (strain ATCC 700610 / UA159)Predicted (SEA)25.3788
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7012.89
Cytochrome P450 2A6 structureClick to view 3D structureCytochrome P450 2A6P11509HumansPredicted (SEA)4024.65
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)4572.94
Click to view 3D structureGamma-aminobutyric acid receptor subunit alpha-6P30191Rattus norvegicusPredicted (SEA)8.40772
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)7454.76
Click to view 3D structureGamma-aminobutyric acid receptor subunit rho-2P28476HumansPredicted (SEA)4.5931
Click to view 3D structureTrace amine-associated receptor 1Q923Y9Rattus norvegicusPredicted (SEA)2976.95
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)7738.06
Concentrations
Not Available
External Links
DrugBank IDDB00847
HMDB IDHMDB0002991
FooDB IDFDB023091
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1808054
BioCyc IDCPD-239
METLIN ID3222
PDB IDNot Available
Wikipedia LinkCysteamine
Chemspider ID5834
ChEBI ID17141
PubChem Compound ID6058
Kegg Compound IDC01678
YMDB IDNot Available
ECMDB IDECMDB24080
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Chakrabarti MC, Le N, Paik CH, De Graff WG, Carrasquillo JA: Prevention of radiolysis of monoclonal antibody during labeling. J Nucl Med. 1996 Aug;37(8):1384-8.
2. Skov Olsen P: Role of epidermal growth factor in gastroduodenal mucosal protection. J Clin Gastroenterol. 1988;10 Suppl 1:S146-51.
3. Gahl WA, Schneider JA, Schulman JD, Thoene JG, Reed GF: Predicted reciprocal serum creatinine at age 10 years as a measure of renal function in children with nephropathic cystinosis treated with oral cysteamine. Pediatr Nephrol. 1990 Mar;4(2):129-35.
4. Smolin LA, Clark KF, Thoene JG, Gahl WA, Schneider JA: A comparison of the effectiveness of cysteamine and phosphocysteamine in elevating plasma cysteamine concentration and decreasing leukocyte free cystine in nephropathic cystinosis. Pediatr Res. 1988 Jun;23(6):616-20.
5. Levtchenko EN, van Dael CM, de Graaf-Hess AC, Wilmer MJ, van den Heuvel LP, Monnens LA, Blom HJ: Strict cysteamine dose regimen is required to prevent nocturnal cystine accumulation in cystinosis. Pediatr Nephrol. 2006 Jan;21(1):110-3. Epub 2005 Oct 27.
6. Lochman P, Adam T, Friedecky D, Hlidkova E, Skopkova Z: High-throughput capillary electrophoretic method for determination of total aminothiols in plasma and urine. Electrophoresis. 2003 Apr;24(7-8):1200-7.
7. Sonies BC, Almajid P, Kleta R, Bernardini I, Gahl WA: Swallowing dysfunction in 101 patients with nephropathic cystinosis: benefit of long-term cysteamine therapy. Medicine (Baltimore). 2005 May;84(3):137-46.
8. Liu YC, Wang CM, Hsiung KP: Comparison of different protein immobilization methods on quartz crystal microbalance surface in flow injection immunoassay. Anal Biochem. 2001 Dec 15;299(2):130-5.
9. Yudkoff M, Foreman JW, Segal S: Effects of cysteamine therapy in nephropathic cystinosis. N Engl J Med. 1981 Jan 15;304(3):141-5.
10. Gahl WA, Charnas L, Markello TC, Bernardini I, Ishak KG, Dalakas MC: Parenchymal organ cystine depletion with long-term cysteamine therapy. Biochem Med Metab Biol. 1992 Dec;48(3):275-85.
11. Geelen JM, Monnens LA, Levtchenko EN: Follow-up and treatment of adults with cystinosis in the Netherlands. Nephrol Dial Transplant. 2002 Oct;17(10):1766-70.
12. Pastore A, Massoud R, Motti C, Lo Russo A, Fucci G, Cortese C, Federici G: Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Clin Chem. 1998 Apr;44(4):825-32.
13. Stachowicz M, Lehmann B, Tibi A, Prognon P, Daurat V, Pradeau D: Determination of total cysteamine in human serum by a high-performance liquid chromatography with fluorescence detection. J Pharm Biomed Anal. 1998 Aug;17(4-5):767-73.
14. Orloff S, Butler JD, Towne D, Mukherjee AB, Schulman JD: Pantetheinase activity and cysteamine content in cystinotic and normal fibroblasts and leukocytes. Pediatr Res. 1981 Jul;15(7):1063-7.
15. de Graaf-Hess A, Trijbels F, Blom H: New method for determining cystine in leukocytes and fibroblasts. Clin Chem. 1999 Dec;45(12):2224-8.
16. Chmiel J, Kopczynski Z, Rybczynska M: The influence of the known radioprotective compounds on the metabolism of red blood cells. I. Effect of cysteamine on the cellular level of the intermediates and coenzymes. Pol J Pharmacol Pharm. 1976;28(2):113-21.
17. Schneider JA, Clark KF, Greene AA, Reisch JS, Markello TC, Gahl WA, Thoene JG, Noonan PK, Berry KA: Recent advances in the treatment of cystinosis. J Inherit Metab Dis. 1995;18(4):387-97.
18. Dominy JE Jr, Simmons CR, Hirschberger LL, Hwang J, Coloso RM, Stipanuk MH: Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase. J Biol Chem. 2007 Aug 31;282(35):25189-98. Epub 2007 Jun 20.
19. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3.
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=17581819
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22735334