Quinidine sulfate dihydrate - CAS 6591-63-5

Quinidine is a voltage-gated sodium channel blocker, exhibiting antimuscarinic and antimalarial properties.

Catalog Number

6591-63-5

CAS

6591-63-5

Synonyms

Chinidin Sodium; Pitayine Sodium; β-quinine Sodium; (+)-quinidine Sodium; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol sulfuric acid dihydrate

Molecular Weight

782.94

Molecular Formula

C40H48N4O4·H2SO4·2H2O

Product Information

Canonical SMILES

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.O.O.OS(=O)(=O)O

InChI

InChI=1S/2C20H24N2O2.H2O4S.2H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4;;/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4);2*1H2/t2*13-,14-,19+,20-;;;/m00.../s1

InChI Key

ZHNFLHYOFXQIOW-AHSOWCEXSA-N

MDL

MFCD00149346

Storage

Inert atmosphere. Keep cold.

Boiling Point

992.5 °C / 760 mmHg

Safety Information

Signal Word

Warning

Precautionary Statement

P264 - P270 - P301+P312+P330 - P501

Reference Reading

1.Structure of 9-epiquinine hydrochloride dihydrate versus antimalarial activity.

Karle JM1, Karle IL. Acta Crystallogr C. 1992 Nov 15;48 ( Pt 11):1975-80.

9-Epiquinine hydrochloride dihydrate [(9S)-6'-methoxycinchonan-9-ol hydrochloride dihydrate], C20H25N2O2+.Cl-.2H2O, M(r) = 396.9, orthorhombic, P212121, a = 8.059 (2), b = 11.537 (3), c = 22.311 (6) A, V = 2074.1 (9) A3, Z = 4, Dx = 1.271 g cm-3, Cu K alpha, lambda = 1.54178 A, mu = 18.58 cm-1, F(000) = 848, room temperature, final R = 6.56% for 1344 reflections with magnitude of Fo > 3 sigma (F). 9-Epiquinine crystallized as a hydrated tertiary amine hydrochloride salt. The intramolecular N(1)+ ...O distance is 2.816 A. All H atoms attached to O or N atoms form intermolecular hydrogen bonds. The Cl ion is involved in four hydrogen bonds including one with the hydroxyl group of 9-epiquinine. The N(1)+-H moiety hydrogen bonds to a water molecule. The O(12)-C(9)...N(1)+-H(1) torsion angle was equal to -0.2 (3.8) degrees in comparison to 97.0 degrees for quinidine sulfate [Karle & Karle (1981). Proc. Natl Acad. Sci. USA, 78, 5938-5941].

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass