CAS 137433-23-9

(R)-Hydroxychloroquine

Description:

(R)-Hydroxychloroquine is a chiral compound belonging to the class of 4-aminoquinoline derivatives, primarily known for its use as an antimalarial and immunomodulatory agent. It is characterized by its ability to inhibit the growth of certain parasites and modulate immune responses, making it valuable in the treatment of diseases such as malaria and autoimmune disorders like rheumatoid arthritis and lupus erythematosus. The compound features a hydroxyl group (-OH) attached to a chloroquine backbone, which enhances its solubility and bioavailability compared to its parent compound, chloroquine. Its stereochemistry, indicated by the (R) designation, plays a crucial role in its pharmacological activity and efficacy. Hydroxychloroquine is typically administered in oral form and is known for its relatively favorable safety profile, although it can cause side effects such as gastrointestinal disturbances and, in rare cases, retinal toxicity. The compound's mechanism of action involves interference with lysosomal function and modulation of cytokine production, contributing to its therapeutic effects in various conditions.

Formula: C₁₈H₂₆ClN₃O

InChI: InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)/t14-/m1/s1

InChI key: InChIKey=XXSMGPRMXLTPCZ-CQSZACIVSA-N

SMILES: N([C@@H](CCCN(CCO)CC)C)C=1C2=C(N=CC1)C=C(Cl)C=C2

Synonyms:

• (R)-Hydroxychloroquine
• 2-[[(4R)-4-[(7-Chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol
• Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, (R)-
• Ethanol, 2-[[(4R)-4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-

(R)-(-)-Hydroxy Chloroquine-d5 Diphosphate

Controlled Product

CAS: 137433-23-9, 158749-75-8

Formula: C₁₈H₂₇D₅ClN₃O₉P₂

Color and Shape: Neat

Molecular weight: 536.89

Ref: TR-H905303

(R)-Hydroxychloroquine (>90%)

Controlled Product

CAS: 137433-23-9

Applications 2-[[(4R)-4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-ethanol is an antimalarial drug more commonly known as (R)-hydroxychloroquine.
References The Canadian Hydroxychloroquine Study Group: N. Engl. J. Med., 324, 150 (1991).

Formula: C₁₈H₂₆ClN₃O

Color and Shape: Neat

Molecular weight: 335.87

Ref: TR-C373710

(R)-(-)-Hydroxy Chloroquine-d4 Diphosphate

Controlled Product

CAS: 137433-23-9, 158749-75-8, 2557418-88-7, 645406-70-8

Formula: C₁₈H₂₂D₄ClN₃O·2(H₃PO₄)

Color and Shape: Neat

Molecular weight: 535.88

Ref: TR-H905302

Hydroxychloroquine R-isomer Impurity

CAS: 137433-23-9

Formula: C₁₈H₂₆ClN₃O

Molecular weight: 335.88

Ref: ST-EA-CP-H4010

(R)-Hydroxychloroquine

CAS: 137433-23-9

(R)-Hydroxychloroquine is the enantiomer of Hydroxychloroquine. Hydroxychloroquine is an agent of synthetic antimalarial.

Formula: C₁₈H₂₆ClN₃O

Purity: 98%

Color and Shape: Solid

Molecular weight: 335.87

Ref: TM-T12622