An active enantiomer of (±)-thalidomide
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Product Categories

Product Type

Biochemicals

Research Area

Immunology & Inflammation
Autoimmunity

(–)-Thalidomide

Item No. 14967

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[(3S)-2,6-dioxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione
CAS Number
841-67-8
Synonyms
  • (L)-Thalidomide
  • NSC 91730
  • (–)-N-Phthaloylgluamimide
Molecular Formula
C13H10N2O4
Formula Weight
258.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: slightly solubleDMSO: slightly solubleMethanol: slightly, heated
SMILES
O=C1N([C@@H]2C(NC(CC2)=O)=O)C(C3=CC=CC=C31)=O
InChi Code
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)/t9-/m0/s1
InChi Key
UEJJHQNACJXSKW-VIFPVBQESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $62

    Add

    10 mg

    $117

    Add

    25 mg

    $274

    Add
    Product Description

    (–)-Thalidomide is an active enantiomer of (±)-thalidomide (Item No. 14610) and has immunomodulatory and teratogenic activities.1,2,3 It enhances TNF-α production induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in HL-60 cells when used at concentrations ranging from 0.1 to 100 µM.1 Preincubation of isolated Rhode Island Red (RIR) chicken donor blood with (–)-thalidomide (10 mg/ml) reduces recipient chicken embryo splenomegaly in a model of graft versus host disease.2 (–)-Thalidomide (150 mg/kg) induces fetal malformations when administered to pregnant female rabbits.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nishimura, K., Hashimoto, Y., and Iwasaki, S. (S)-form of α -methyl-N( α )-phthalimidoglutarimide, but not its (R)-form, enhanced phorbol ester-induced tumor necrosis factor-α production by human leukemia cell HL-60: Implication of optical resolution of thalidomidal effects. Chem. Pharm. Bull. (Tokyo) 42(5), 1157-1159 (1994).

    2. Field, E.O., Gibbs, J.E., Tucker, D.F., et al. Effect of thalidomide on the graft versus host reaction. Nature 211(5055), 1308-1310 (1966).

    3. Fabro, S., Smith, R.L., and Williams, R.T. Toxicity and teratogenicity of optical isomers of thalidomide. Nature 215(5098), 296 (1967).