CAS 53467-23-5

(9S)-6′-Methoxycinchonan-3,9-diol

Description:

(9S)-6′-Methoxycinchonan-3,9-diol, with the CAS number 53467-23-5, is a chemical compound that belongs to the class of cinchona alkaloids, which are derived from the bark of the cinchona tree. This compound features a complex bicyclic structure that includes a methoxy group and two hydroxyl groups, contributing to its unique chemical properties. It is characterized by its stereochemistry, specifically the (9S) configuration, which plays a crucial role in its biological activity. The presence of hydroxyl groups typically enhances solubility in polar solvents and can influence interactions with biological targets, making it of interest in medicinal chemistry. Compounds like this one are often studied for their potential pharmacological effects, including antimalarial and analgesic properties, due to their structural similarity to other bioactive alkaloids. Additionally, the methoxy group can affect the compound's lipophilicity and overall reactivity. As with many alkaloids, the synthesis and extraction of (9S)-6′-Methoxycinchonan-3,9-diol are of interest for both research and therapeutic applications.

Formula: C₂₀H₂₄N₂O₃

InChI: InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18+,19-,20+/m0/s1

InChI key: InChIKey=BSRUJCFCZKMFMB-LGWHJFRWSA-N

SMILES: [C@H](O)(C=1C2=C(C=CC(OC)=C2)N=CC1)[C@@]3([N@@]4C[C@@](C=C)(O)[C@](C3)(CC4)[H])[H]

Synonyms:

• 3-Hydroxyquinidine
• (3S)-3-Hydroxyquinidine
• Cinchonan-3,9-diol, 6′-methoxy-, (9S)-
• (3S)-Hydroxyquinidine
• (9S)-6′-Methoxycinchonan-3,9-diol

(3S)-3-Hydroxy Quinidine

CAS: 53467-23-5

Formula: C₂₀H₂₄N₂O₃

Color and Shape: White To Off-White Solid

Molecular weight: 340.42

Ref: 4Z-Q-042

(3S)-hydroxy Quinidine

CAS: 53467-23-5

(3S)-hydroxy Quinidine is a potent metabolite of antiarrhythmic quinidine, mainly formed by CYP3A4, prevents fibrillation and tachycardia.

Formula: C₂₀H₂₄N₂O₃

Color and Shape: Solid

Molecular weight: 340.42

Ref: TM-T36561

(3S)-3-Hydroxy Quinidine

Controlled Product

CAS: 53467-23-5

Applications The major metabolite of the Cinchona alkaloid Quinidine.
References Small, D.L., et al.: J. Chem. Med., 22, 1014 (1979), Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1982), Rakhir, A., et al.: J. Pharmacokinet. Biopharm., 12, 1 (1984), Christie, D.J., et al.: J. Lab. Clin. Med., 112, 92 (1988),

Formula: C₂₀H₂₄N₂O₃

Color and Shape: Neat

Molecular weight: 340.42

Ref: TR-H953230

(3S)-3-Hydroxy Quinidine-vinyl-d3

Controlled Product

CAS: 53467-23-5

Applications The major metabolite of the Cinchona alkaloid Quinidine.
References Small, D.L., et al.: J. Chem. Med., 22, 1014 (1979), Guentert, T.W., et al.: Eur. J. Drug Metab. Pharmacokinet., 7, 31 (1982), Rakhir, A., et al.: J. Pharmacokinet. Biopharm., 12, 1 (1984), Christie, D.J., et al.: J. Lab. Clin. Med., 112, 92 (1988),

Formula: C₂₀H₂₁D₃N₂O₃

Color and Shape: Neat

Molecular weight: 343.43

Ref: TR-H953232

(3S)-3-Hydroxy quinidine

CAS: 53467-23-5

Quinine is an alkaloid that is extracted from the bark of the Cinchona tree. It has a variety of pharmacological effects, including anti-malarial and anti-bacterial properties. However, quinine can cause serious adverse reactions due to its toxicity and potential for drug interactions. Quinine is metabolized in the human body by cyp3a4 enzymes into 3-hydroxyquinidine (3HQ). 3HQ has been shown to reduce renal clearance and increase glomerular filtration rate in rats. The concentration–time curve for 3HQ shows a rapid decline in plasma concentration after administration, which may be due to its high clearance rate. This drug also has pharmacokinetic properties that are similar to those of quinine, with an elimination half-life of about 2 hours in humans. 3HQ is not detected in the blood after administration, so it must be prepared before analysis using an experimental model or analytical method such as fluorescence detection.

Formula: C₂₀H₂₄N₂O₃

Purity: Min. 95 Area-%

Color and Shape: White Powder

Molecular weight: 340.42 g/mol

Ref: 3D-FH24113