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T144 Sigma-Aldrich

(±)-Thalidomide

≥98%, powder

Synonym: (±)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

  • CAS Number 50-35-1

  • Empirical Formula (Hill Notation) C13H10N2O4

  • Molecular Weight 258.23

  •  EC Number 200-031-1

  •  MDL number MFCD00153873

  •  eCl@ss 39180303

  •  PubChem Substance ID 24278765

  •  NACRES NA.77

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Properties

Related Categories Angiogenesis, Angiogenesis Inhibitors, Angiogenesis Regulators, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index,
assay   ≥98%
form   powder
color   white
solubility   DMSO: 20 mg/mL, clear
originator   Celgene
SMILES string   O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
InChI   1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)
InChI key   UEJJHQNACJXSKW-UHFFFAOYSA-N
Gene Information   human ... LITAF(9516), TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

Description

Application

Thalidomide has been used to study its neuropathological effects in mouse models of Alzheimer′s disease (AD). This study reported that long term administration of thalidomide causes beta-secretase inhibition and subsequently alleviates amyloid-like pathology. Furthermore, thalidomide has also been used to evaluate its teratogenic functions. Thalidomide was found to affect endodermal differentiation and neural development in differentiating human embryonic and induced pluripotent stem cells.

Packaging

1 g in glass bottle

100 mg in glass bottle

Biochem/physiol Actions

(±)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). It also functions as an inhibitor of angiogenesis, an immunosuppressive agent, a sedative and a teratogen. Furthermore, thalidomide is known to exhibit antitumor functions in refractory multiple myeloma.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Thalidomide is soluble in DMSO at a concentration that is more than 20 mg/ml. It is insoluble in water and ethanol.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T144.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
TI4375000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

HPLC Analysis of Thalidomide Enantiomers on Astec® CHIROBIOTIC® V2

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Thalidomide Enantiomers on Astec® CHIROBIOTIC® V2
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

HPLC Analysis of Thalidomide Enantiomers on Astec® CHIROBIOTIC® V

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Thalidomide Enantiomers on Astec® CHIROBIOTIC® V
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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904872 Pomalidomide-PEG2-butyl azide, ≥95%
904864 (S,R,S)-AHPC-PEG6-butyl azide, ≥95%
905224 Pomalidomide-PEG6-butyl amine hydrochloride, ≥95%

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