CAS 2614-06-4

(+)-Thalidomide

Description:

(+)-Thalidomide, with the CAS number 2614-06-4, is a pharmaceutical compound known for its complex history and diverse biological effects. It is a chiral molecule, existing as a racemic mixture, but the (+) enantiomer is primarily associated with its therapeutic properties. Thalidomide is characterized by its low solubility in water and moderate solubility in organic solvents, which influences its bioavailability and pharmacokinetics. The compound exhibits immunomodulatory, anti-inflammatory, and anti-angiogenic properties, making it useful in treating conditions such as multiple myeloma and leprosy-related complications. However, it is also notorious for its teratogenic effects when administered during pregnancy, leading to severe birth defects. As a result, its use is strictly regulated, and it is often prescribed under controlled conditions. The mechanism of action involves modulation of tumor necrosis factor-alpha (TNF-α) and other cytokines, contributing to its therapeutic effects. Overall, (+)-Thalidomide remains a significant example of the dual nature of pharmaceuticals, highlighting the importance of careful consideration in drug development and usage.

Formula: C₁₃H₁₀N₂O₄

InChI: 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-/m1/s1

InChI key: InChIKey=UEJJHQNACJXSKW-SECBINFHSA-N

SMILES: O=C1N(C(=O)C=2C1=CC=CC2)[C@H]3C(=O)NC(=O)CC3

Synonyms:

• (+)-Thalidomide
• 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (R)-
• 1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (R)- (9CI)
• 1H-Isoindole-1,3(2H)-dione, 2-[(3R)-2,6-dioxo-3-piperidinyl]-
• 2-[(3R)-2,6-Dioxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione
• 2-[(3R)-2,6-Dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione
• D-Thalidomide
• NSC 91729
• Phthalimide, N-(2,6-dioxo-3-piperidyl)-, (+)-
• Phthalimide, N-(2,6-dioxo-3-piperidyl)-, <span class="text-smallcaps">D</span>-(+)-
• Phthalimide, N-(2,6-dioxo-3-piperidyl)-, D-(+)-
• R-(+)-Thalidomide
• R-(<span class="text-smallcaps">D</span>)-Thalidomide

(R)-Thalidomide

CAS: 2614-06-4

(R)-Thalidomide

Purity: ≥98%

Molecular weight: 258.23g/mol

Ref: 54-BUP21073

R-Thalidomide

CAS: 2614-06-4

Formula: C₁₃H₁₀N₂O₄

Molecular weight: 258.24

Ref: 4Z-T-233

(R)-(+)-Thalidomide

Controlled Product

CAS: 2614-06-4

Applications Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.
References D’Amato, r.J., et al.: Proc. Natl. Acad. Sci. USA, 91, 4082 (1994), Makonkawkeyoon, S., et al.: Proc. Natl. Acad. Sci. USA, 90, 5974 (1993), Schumacher, H., et al.: J. Pharmacol. Exp. Therap., 160, 189 (1968)

Formula: C₁₃H₁₀N₂O₄

Color and Shape: Neat

Molecular weight: 258.23

Ref: TR-T338855

(R)-Thalidomide

CAS: 2614-06-4

(R)-Thalidomide is a COX 1/2 inhibitor that induces apoptosis in MCF-7, IM-9, HS-Sultan, KB and other cancer cells.

Formula: C₁₃H₁₀N₂O₄

Purity: 99.87%

Color and Shape: Solid

Molecular weight: 258.23

Ref: TM-T12644