An internal standard for the quantification of (±)-thalidomide
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Unlabeled Version(s)
14610(±)-Thalidomide
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(±)-Thalidomide-d4

Item No. 29450

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione-4,5,6,7-d4
CAS Number
1219177-18-0
Synonyms
  • N-Phthaloylglutamimide-d4
Molecular Formula
C13H6D4N2O4
Formula Weight
262.3
Purity
≥99% deuterated forms (d1-d4)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 12 mg/mlDMSO: 12 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.11 mg/ml
SMILES
O=C(C1=C2C([2H])=C([2H])C([2H])=C1[2H])N(C3C(NC(CC3)=O)=O)C2=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)/i1D,2D,3D,4D
InChi Key
UEJJHQNACJXSKW-RHQRLBAQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    Product Description

    (±)-Thalidomide-d4 is intended for use as an internal standard for the quantification of (±)-thalidomide (Item No. 14610) by GC- or LC-MS. (±)-Thalidomide is an immunomodulatory compound with diverse biological activities, including anticancer, anti-inflammatory, and teratogenic properties.1,2,3 It prevents polymorphonuclear leukocyte (PMN) chemotaxis when used at concentrations of 1, 10, and 100 µg/ml.1 (±)-Thalidomide increases IL-2-induced proliferation and IFN-γ production in primary human T cells in vitro.2 It enhances natural killer (NK) cell-mediated cytotoxicity in MM.1S multiple myeloma cells.3 Thalidomide (4 mg/animal) reduces lung IL-6, TGF-β, VEGF, angiopoietin-1, angiopoietin-2, and collagen type Iα1 expression, inhibits pulmonary angiogenesis, and attenuates fibrosis in a mouse model of bleomycin-induced pulmonary fibrosis.4 It induces apoptosis in primary human embryonic fibroblasts (EC50 = 8.9 µM) and induces limb and eye defects in chicken embryos (EC50 = 50 µg/kg egg weight).5 Formulations containing thalidomide have been used in the treatment of multiple myeloma and erythema nodosum leprosum (ENL) in non-pregnant individuals.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Faure, M., Thivolet, J., and Gaucherand, M. Inhibition of PMN leukocytes chemotaxis by thalidomide. Arch. Dermatol. Res. 269(3), 275-280 (1980).

    2. Haslett, P.A., Corral, L.G., Albert, M., et al. Thalidomide costimulates primary human T lymphocytes, preferentially inducing proliferation, cytokine production, and cytotoxic responses in the CD8+ subset. J. Exp. Med. 187(11), 1885-1892 (1998).

    3. Davies, F.E., Raje, N., Hideshima, T., et al. Thalidomide and immunomodulatory derivatives augment natural killer cell cytotoxicity in multiple myeloma. Blood 98(1), 210-216 (2001).

    4. Tabata, C., Tabata, R., Kadokawa, Y., et al. Thalidomide prevents bleomycin-induced pulmonary fibrosis in mice. J. Immunol. 179(1), 708-714 (2007).

    5. Knobloch, J., Shaughnessy, J.D., Jr., and Rüther, U. Thalidomide induces limb deformities by perturbing the Bmp/Dkk1/Wnt signaling pathway. The FASEB Journal 21(7), 1410-1421 (2007).