(R)-Thalidomide

HCID 75792

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Basic information

CAS: 2614-06-4
Standard SMILES: O=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
InChIKey: UEJJHQNACJXSKW-SECBINFHSA-N
Molecular formula: C13H10N2O4
Average molar mass: 258.23 g/mol
Monoisotopic mass: 258.0640568

Overview

(R)-thalidomide is a 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has R-configuration at the chiral centre. It has a role as a sedative. It is an enantiomer of a (S)-thalidomide.

Names & identifiers

Preferred name: (R)-Thalidomide
IUPAC: 2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione
English name: (R)-(+)-THALIDOMIDE
Molecular formula: C13H10N2O4
Molecular weight: 258.23

Names & synonyms

(R)-Thalidomide(+)-ThalidomideD-ThalidomideR-(+)-ThalidomideThalidomide, (R)-QN61H68KLKNSC 91729(R)-(D)-ThalidomideR-(D)-THALIDOMIDEUNII-QN61H68KLK(+)-(R)-THALIDOMIDEDTXSID6046971

Show more names

(R)-(+)-THALIDOMIDEThalidomide (R)-Isomer6-dioxo-3-piperidyl)-n-(d-(+)-phthalimidN-[(R)-2,6-Dioxopiperidine-3-yl]phthalimide(+)-N-[(R)-2,6-Dioxo-3-piperidinyl]phthalimide2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione6-dioxo-3-piperidinyl)-3(2h)-dion(r)-1h-isoindole-2-(2(3R)-3-(1,3-Dioxo-2H-isoindole-2-yl)piperidine-2,6-dione

CHEBI:619172-[(3R)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dionePhthalimide, N-(2,6-dioxo-3-piperidyl)-, (+)-NSC-917291H-ISOINDOLE-1,3(2H)-DIONE, 2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE2-((3R)-2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dioneRefChem:70338

Database identifiers

CAS: 2614-06-4
PubChem CID: 75792
DTXSID: DTXSID6046971
ChEMBL: CHEMBL558551
ChEBI: CHEBI:61917
UNII: QN61H68KLK
EC Number: 636-759-5
Nikkaji: J15.228E

Properties

Computed structural properties

XLogP: 0.3
Topological polar surface area: 83.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 19
Formal charge: 0
Complexity: 449

Experimental & physicochemical properties

SpringerMaterials PropertiesCrystal structure

Physicochemical properties

Melting point: 269 · 269-271°C
Boiling point: 401.48 °C · 401.48°C (rough estimate)
Density: 1.2944 · 1.2944 (rough estimate)
refractive index: 1.53 · 1.5300 (estimate)
storage temp.: -20 °C · -20°C Freezer
solubility: DMSO: soluble
form: solid
pka: 10.7 · 10.70±0.40(Predicted)
color: white
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
InChIKey: UEJJHQNACJXSKW-SECBINFHSA-N
SMILES: O=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1
FDA UNII: 61 H68KLK · QN61H68KLK
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07,GHS08
Signal word: Danger
Hazard statements: 302 · H302-H360
Precautionary statements: 201 · P201-P301+P312+P330-P308+P313
PPE: 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: T
Risk Statements: 61 · 61-22
Safety Statements: 53 · 53-36/37/39-45
WGK Germany: 3 · 3
RTECS: 4925000 · TI4925000
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 4 OralRepr · Acute Tox. 4 OralRepr. 1B

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: TI4925000
risk_code: 61-22
Signal word: Danger
Symbol(GHS): GHS07,GHS08
hazard_code: T
safety_code: 53-36/37/39-45
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements: H302-H360
Hazard Classifications: Acute Tox. 4 OralRepr. 1B
Precautionary statements: P201-P301+P312+P330-P308+P313

Chemistry & industry

Applications · 2 items

UsesOptically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative.

UsesThalidomide 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.

Upstream & downstream products

Upstream raw materials

Suppliers29 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

艾吉析科技（上海）有限公司17717235263 · [email protected]

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]

江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]

Additional notes

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

Related reactions

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Compound notes

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