Quinidine sulfate dihydrate

Iupac Name：(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;sulfuric acid

Molecular Weight：422.5

Modify Date.: 2022-12-12 21:38

Introduction: Quinidine sulfate dihydrate is the sulfateof an alkaloid obtained from various species ofCinchona and their hybrids. It is a dextrorotatory diastereoisomerof quinine. The salt crystallizes from wateras the dihydrate, in the form of fine, needlelike, white crystals.Quinidine sulfate contains a hydroxymethyl groupthat serves as a link between a quinoline ring and a quinuclidinemoiety. The structure contains two basic nitrogens,of which the quinuclidine nitrogen is the stronger base(pKa 10). Quinidine sulfate dihydrate is bitter and light sensitive.Quinidine sulfate dihydrates are nearly neutral or slightly alkaline. Itis soluble to the extent of 1% in water and more highly solublein alcohol or chloroform. View more+

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1. Names and Identifiers

1.1 Name: Quinidine sulfate dihydrate
1.2 Synonyms: 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol hemisulfate hydrate Cinchonan-9-ol, 6'-methoxy-, (9S)-, sulfate (2:1) (salt), monohydrate Quinidin Quinidine dihydrate sulfate salt Quinidine sulfate (2:1) (salt) monohydrate Quinidine sulfate dehydrate Quinidine sulfate hydrate Quinidine sulfate monohydrate

1.3 CAS No.: 6591-63-5

1.4 CID: 656862

1.5 EINECS(EC#): 678-472-8

1.6 Molecular Formula: C20H26N2O6S (isomer)

1.7 Inchi: InChI=1/C20H24N2O2.H2O4S/c1-3-13-12-22-9-7-14(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/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t13-,14-,19+,20-;/s2

1.8 InChkey: AKYHKWQPZHDOBW-VLRFBITDNA-N

1.9 Canonical Smiles: OS(O)(=O)=O.[H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)C1=CC=NC2=CC=C(OC)C=C12

1.10 Isomers Smiles: COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.O.O.OS(=O)(=O)O

2. Properties

2.1 Melting point: 212-214?°C (dec.)(lit.)

2.1 Boiling point: 495.9°Cat760mmHg

2.1 Refractive index: 275 ° (C=2, 0.1mol/L HCl)

2.1 Flash Point: 253.7°C

2.1 Precise Quality: 746.33500

2.1 PSA: 174.16000

2.1 logP: 6.65020

2.1 Appearance: Powder

2.2 Storage: Light Sensitive. Ambient temperatures.

2.3 Chemical Properties: Quinidine sulfate dihydrate is white to light yellow crystal powde

2.4 Color/Form: Occurs as fine, needle-like, white crystals which frequently cohere in masses or as a fine, white powder.

2.5 Decomposition: When heated to decomposition it emits very toxic fumes of /nitrogen oxides and sulfur oxides/.

2.6 Water Solubility: Soluble in chloroform, water (11 mg/ml at 20°C), alcohol, and ethanol (50 mg/ml).

2.7 Spectral Properties: IR: 8162 (Sadtler Research Laboratories IR Grating Collection)
UV: 11429 (Sadtler Research Laboratories Spectral Collection)

2.8 Stability: PROTECT FROM LIGHT; DARKENS ON EXPOSURE TO LIGHT /DIHYDRATE/

2.9 StorageTemp: under inert gas (nitrogen or Argon) at 2-8°C

3. Use and Manufacturing

3.1 General Description: Quinidine sulfate dihydrate is the sulfateof an alkaloid obtained from various species ofCinchona and their hybrids. It is a dextrorotatory diastereoisomerof quinine. The salt crystallizes from wateras the dihydrate, in the form of fine, needlelike, white crystals.Quinidine sulfate contains a hydroxymethyl groupthat serves as a link between a quinoline ring and a quinuclidinemoiety. The structure contains two basic nitrogens,of which the quinuclidine nitrogen is the stronger base(pKa 10). Quinidine sulfate dihydrate is bitter and light sensitive.Quinidine sulfate dihydrates are nearly neutral or slightly alkaline. Itis soluble to the extent of 1% in water and more highly solublein alcohol or chloroform.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1158 companies from 5 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria by 134 of 1158 companies. For more detailed information, please visit ECHA C&L website

Of the 3 notification(s) provided by 1024 of 1158 companies with hazard statement code(s):

H341 (98.24%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501

3.3 Usage: antiarrhythmic, antimalarial

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: 22-20/21/22

4.1 Safety Statements: 13-36

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl quinidine sulfate, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.

4.2 Packing Group: III

4.2 Hazard Class: 6.1

4.2 Hazard Declaration: H302

4.2 RIDADR: UN 2811 6.1/PG III

4.2 Caution Statement: P301 + P312 + P330

4.2 Formulations/Preparations: QUINIDINE SULFATE CONTAINS 82% OF QUINIDINE BASE BY WEIGHT ... .
QUINIDINE SULFATE AVAILABLE ... CAPSULES, CONTAIN 100 ... MG OF THE DRUG; TABLETS OF QUINIDINE POLYGALACTURONATE CONTAIN 275 MG, EQUIVALENT TO 200 MG OF QUINIDINE SULFATE. PREPN FOR SLOW ABSORPTION ARE ALSO AVAILABLE AS 300 MG EXTENDED RELEASE TABLET OF QUINIDINE SULFATE & A 324 MG TABLET OF GLUCONATE. QUINIDINE SULFATE IS ALSO AVAILABLE AS AN INJECTION IN 1 ML AMPULE CONTAINING 200 MG/ML. THE NECESSARY DOSE IS DILUTED TO 800 MG/50 ML IN 5% GLUCOSE SOLUTION AND IS INJECTED AT THE RATE OF 16 MG/MIN, WITH CONTINUOUS OBSERVATION OF THE PATIENT & OF THE ECG.
Oral Tablets extended release 324 mg (equivalent to quinidine 202 mg), Quinaglute Dura-Tabs, Berlex, Quinatime, CMC; 330 mg (equivalent to quinidine 206 mg), Duraquine (with povidone), Warner Chilcott; Parenteral injection, 80 mg (equivalent to quinidine 50 mg) per ml, quinidine gluconate injection (with edetate disodium and phenol). Lilly /Quinidine Gluconate/
Oral Tablets 275 mg (equivalent to quinidine sulfate 200 mg), Cardioquin (with povidone; scored), Purdue Frederick. /Quinidine polygalacturonate/
Oral Tablets, 200 mg, 300 mg, Quinora, Key; Tablets, extended-released, 300 mg, Quinidex Extentabs, Robins /Quinidine Sulfate/
Capsules and tablets 100, 200, and 300 mg. Controlled release tablets, 300 mg. Ampules, 200 mg/ml.
QUINIDINE SULFATE IS AVAILABLE AS TABLETS (100 TO 300 MG) CAPSULES 200, AND 300 MG. 300 MG SUBSTAINED RELEASE TABLETS (QUINIDEX) ARE AVAILABLE, AS IS AN INJECTION (200 MG/ML). PREPARATIONS OF THE GLUCONATE AND POLYGALACTURONATE SALTS ARE ALSO MARKETED.

4.3 WGK Germany: 3

4.3 RTECS: VA5605000

4.3 Report: Reported in EPA TSCA Inventory.

4.4 Safety: Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and subcutaneous routes. Human systemic effects: arrythmias, cholestatic conjunctive irritation, cyanosis, death, distorted perceptions, dyspnea, fever, hallucinations, hepatitis, increased body temperature, irritative dermatitis, jaundice, joints effects, liver function impairment, other vascular and pulmonary changes, somnolence, transaminases changes, tremors, tumors. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.
Safety Information of Quinidinesulfate(2:1)(salt) (50-54-4):
Risk Statements: 22
22: Harmful if swallowed
Safety Statements: 22-45
22: Do not breathe dust
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR: 1544

4.5 Specification: Safety Statements:22-45
22:Do not breathe dust
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)

4.6 Toxicity

1.	orl-man TDLo:240 mg/kg/2W-I:EYE	JTCTDW Journal of Toxicology, Clinical Toxicology. 20 (1983),367.
2.	orl-wmn TDLo:272 mg/kg/17D-I:CVS	AIMDAP Archives of Internal Medicine. 145 (1985),2051.
3.	orl-man TDLo:40 mg/kg/2W-I:CVS	AIMDAP Archives of Internal Medicine. 145 (1985),2051.
4.	orl-hmn TDLo:9600 mg/kg/8W:CNS,PUL	JAMAAP JAMA, Journal of the American Medical Association. 238 (1977),884.
5.	orl-wmn TDLo:409 g/kg/14Y:CNS	JAMAAP JAMA, Journal of the American Medical Association. 237 (1977),2093.
6.	orl-man TDLo:88 mg/kg/10D-I:SYS	GASTAB Gastroenterology. 70 (1976),1136.
7.	orl-wmn TDLo:32 mg/kg/2D:SKN	DICPBB Drug Intelligence and Clinical Pharmacy. 16 (1982),615.
8.	mul-man LDLo:30 mg/kg/2D-I:CVS,PUL	AIMEAS Annals of Internal Medicine. 16 (1942),571.
9.	orl-rat LD50:456 mg/kg	ARZNAD Arzneimittel-Forschung. Drug Research. 18 (1968),1127.
10.	ipr-rat LDLo:140 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 1 (1959),156.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Other Information

7.0 Usage: Quinidine sulfate dihydrate, 98+% is used as a A Na+ channel blocker.

7.1 Merck: 14,8060

7.2 Target: Value

7.3 Chemical Properties: Quinidine sulfate dihydrate is white to light yellow crystal powde

7.4 Uses: antiarrhythmic, antimalarial

7.5 Uses: Quinidine sulfate dihydrate (cas# 6591-63-5) is the hydrated, sulfate salt of Quinidine (Q685000), a dextrorotatory stereoisomer of Quinine. Antiarrhythmic (class IA). Antimalarial.

7.6 Brand name: Cin-Quin (Solvay Pharmaceuticals); Quinidex (Wyeth); Quinora (Schering).

7.7 General Description: Quinidine sulfate dihydrate is the sulfateof an alkaloid obtained from various species ofCinchona and their hybrids. It is a dextrorotatory diastereoisomerof quinine. The salt crystallizes from wateras the dihydrate, in the form of fine, needlelike, white crystals.Quinidine sulfate contains a hydroxymethyl groupthat serves as a link between a quinoline ring and a quinuclidinemoiety. The structure contains two basic nitrogens,of which the quinuclidine nitrogen is the stronger base(pKa 10). Quinidine sulfate dihydrate is bitter and light sensitive.Quinidine sulfate dihydrates are nearly neutral or slightly alkaline. Itis soluble to the extent of 1% in water and more highly solublein alcohol or chloroform.

7.8 Biochem/physiol Actions: Class IA antiarrhythmic; potassium channel blocker.

7.9 Clinical Use: Quinidine sulfate is the prototype of antiarrhythmicdrugs and a class IA antiarrhythmic agent according to theVaughan Williams classification. It reduces Na⁺ current bybinding the open ion channels (i.e., state A). The decreasedNa⁺entry into the myocardial cell depresses phase 4 diastolicdepolarization and shifts the intracellular threshold potentialtoward zero. These combined actions diminish thespontaneous frequency of pacemaker tissues, depress theautomaticity of ectopic foci, and, to a lesser extent, reduceimpulse formation in the SA node. This last action results inbradycardia. During the spike action potential, quinidinesulfate decreases transmembrane permeability to passiveinflux of Na⁺, thus slowing the process of phase 0 depolarization,which decreases conduction velocity. This is shownas a prolongation of the QRS complex of electrocardiograms.Quinidine sulfate also prolongs action potential duration,which results in a proportionate increase in the QTinterval. It is used to treat supraventricular and ventricularectopic arrhythmias, such as atrial and ventricular prematurebeats, atrial and ventricular tachycardia, atrial flutter, andatrial fibrillation.

8. Computational chemical data

Molecular Weight: 422.5g/mol
Molecular Formula: C₂₀H₂₆N₂O₆S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 782.35606511
Monoisotopic Mass: 782.35606511
Complexity: 538
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 6
Hydrogen Bond Acceptor Count: 14
Topological Polar Surface Area: 176
Heavy Atom Count: 55
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 5
CACTVS Substructure Key Fingerprint: AAADcfB/vABAAAAAAAAAAAAAAAAAAAAAAAA8eLFiwAAAAACx/gAAHgAACAAADTzhngY+xvMIFoCgAzRnRDCCiCAxIiAI2CA+bJgONuLEsZuEcChkwBHY+Aew4PwOgEABAAACAAAAgAIAAAQAAAAAAAAAAA==

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