2614-06-4

Basic information

• Product Name: (R)-(+)-THALIDOMIDE
• Synonyms: (R)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3-(2H)-DIONE;R-(+)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE;(R)-(+)-THALIDOMIDE;6-dioxo-3-piperidinyl)-3(2h)-dion(r)-1h-isoindole-2-(2;6-dioxo-3-piperidyl)-n-(d-(+)-phthalimid;(+)-2-[(R)-2,6-Dioxo-3-piperidinyl]-1H-isoindole-1,3(2H)-dione;(+)-N-[(R)-2,6-Dioxo-3-piperidinyl]phthalimide;(3R)-3-(1,3-Dioxo-2H-isoindole-2-yl)piperidine-2,6-dione
• CAS NO: 2614-06-4
• Molecular Formula: C₁₃H₁₀N₂O₄
• Molecular Weight: 258.23
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 2614-06-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 269-271°C
• Boiling Point: 401.48°C (rough estimate)
• Flash Point: 262.1°C
• Appearance: white/solid
• Density: 1.2944 (rough estimate)
• Vapor Pressure: 1.65E-10mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: DMSO: soluble
• PKA: 10.70±0.40(Predicted)
• CAS DataBase Reference: (R)-(+)-THALIDOMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-THALIDOMIDE(2614-06-4)
• EPA Substance Registry System: (R)-(+)-THALIDOMIDE(2614-06-4)

Safety Data

• Hazard Codes: T
• Statements: 61-22
• Safety Statements: 53-36/37/39-45
• WGK Germany: 3
• RTECS: TI4925000
• Hazardous Substances Data: 2614-06-4(Hazardous Substances Data)

Usage

Chemical Properties

Needles

Uses

Different sources of media describe the Uses of 2614-06-4 differently. You can refer to the following data:
1. Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.
2. Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative
3. Thalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

Definition

ChEBI: A 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has R-configuration at the chiral centre.

Biochem/physiol Actions

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.

InChI:InChI=1/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

Upstream product

• 85-44-9 phthalic anhydride 
• 841-67-8 (S)-thalidomide 

Downstream Products

• 2614-09-7 (R)-4-phthalimidoglutaramic acid 
• 841-67-8 (S)-thalidomide 
• 2110-19-2 (R)-2-phthalimidoglutaramic acid 
• 131-68-0 α-(o-carboxybenzamido)-D-glutarimide 

Relevant articles and documents

Chiral inversion and hydrolysis of thalidomide: Mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites

The chiral inversion and hydrolysis of thalidomide and the catalysis by bases and human serum albumin were investigated by using a stereoselective HPLC assay. Chiral inversion was catalyzed by albumin, hydroxyl ions, phosphate, and amino acids. Basic amino acids (Arg and Lys) had a superior potency in cataLyzing chiral inversion compared to acid and neutral ones. The chiral inversion of thalidomide is thus subject to Specific and general base catalysis, and it is suggested that the ability of HSA to catalyze the reaction is due to the basic groups of the amino acids Arg and Lys and not to a single catalytic site on the macromolecule. The hydrolysis of thalidomide was also base-catalyzed. However, albumin had no effect on hydrolysis, and there was no difference between the catalytic potencies of acidic, neutral, and basic amino acids. This may be explained by different reaction mechanisms of the chiral inversion and hydrolysis of thalidomide. Chiral inversion is deduced to occur by electrophilic substitution involving specific and general base catalysis, whereas hydrolysis is thought to occur by nucleophilic substitution involving specific and general base as well as nucleophilic catalysis. As nucleophilic attack is sensitive to steric properties of the catalyst, steric hindrance might be the reason albumin is not able to catalyze hydrolysis. 1H NMR experiments revealed that the three teratogenic metabolites of thalidomide, in sharp contrast to the drug itself, had complete chiral stability. This leads to the speculation that, were some enantioselectivity to exist in the teratogenicity of thalidomide, it could result from fast hydrolysis to chirally stable teratogenic metabolites.