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QUINIDINE

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Name

QUINIDINE

EINECS 200-279-0
CAS No. 56-54-2 Density 1.218 g/cm3
PSA 45.59000 LogP 3.11110
Solubility water: 0.05 g/100 mL (20 °C) Melting Point 168-172 °C(lit.)
Formula C20H24N2O2 Boiling Point 495.9 °C at 760 mmHg
Molecular Weight 324.423 Flash Point 253.7 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to light yellow crystal powder
Safety 36-22 Risk Codes 22-20/21/22
Molecular Structure Molecular Structure of 56-54-2 (Quinidine) Hazard Symbols HarmfulXn
Synonyms

Quinidine(8CI);(+)-Quinidine;(8R,9S)-Quinidine;Chinidin;Conchinin;Conchinine;Kinidin;Pitayin;Pitayine;b-Quinidine;b-Quinine;

Article Data 58

QUINIDINE Synthetic route

865853-19-6

(3R,4S)-4-[(2S,3S)-3-(6-Methoxy-quinolin-4-yl)-oxiranylmethyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

56-54-2

quinidine

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide; tert-butyl alcohol at 110℃; for 12h;98%
1207974-84-2

2-(trimethylsilyl)ethyl 6-methoxy-4-((2R,3R)-3-(((3R,4S)-1-((2-(trimethylsilyl)ethoxy)carbonyl)-3-vinylpiperidin-4-yl)methyl)oxiran-2-yl)quinoline-1(2H)-carboxylate

56-54-2

quinidine

Conditions
ConditionsYield
Stage #1: 2-(trimethylsilyl)ethyl 6-methoxy-4-((2R,3R)-3-(((3R,4S)-1-((2-(trimethylsilyl)ethoxy)carbonyl)-3-vinylpiperidin-4-yl)methyl)oxiran-2-yl)quinoline-1(2H)-carboxylate With cesium fluoride In N,N-dimethyl-formamide at 180℃; for 0.25h; Microwave irradiation;
Stage #2: With oxygen In N,N-dimethyl-formamide at 20℃; for 19h;
78%
130-95-0

Quinine

56-54-2

quinidine

Conditions
ConditionsYield
With 9-fluorenone; 2-Heptanol; sodium compound of heptan-2-ol
6'-methoxy-cinchonan-9-one

6'-methoxy-cinchonan-9-one

A

56-54-2

quinidine

B

130-95-0

Quinine

Conditions
ConditionsYield
With sodium isopropylate; toluene
With 2-pentanol; sodium
141-52-6

sodium ethanolate

569329-55-1

6'-methoxy-cinchonan-9-one

aluminium

aluminium

A

56-54-2

quinidine

B

130-95-0

Quinine

Conditions
ConditionsYield
quininone;
quininone

quininone

A

56-54-2

quinidine

B

130-95-0

Quinine

Conditions
ConditionsYield
With ethanol; sodium ethanolate; aluminium
67-63-0

isopropyl alcohol

14528-53-1

6'-methoxycinchoninone

71-36-3

butan-1-ol

sodium alkylates

sodium alkylates

pentan-3-ol; compound 5:2,4-dimethyl-pentan-3-ol; compound 6:cyclohexanol

pentan-3-ol; compound 5:2,4-dimethyl-pentan-3-ol; compound 6:cyclohexanol

B

56-54-2

quinidine

C

130-95-0

Quinine

110-86-1

pyridine

C59H60FeN7O6

A

25875-12-1

Fe(protoporphyrin-IX)(pyridine)2(1+)

B

56-54-2

quinidine

Conditions
ConditionsYield
In acetonitrile Equilibrium constant;

C54H55FeN6O6

15489-90-4

ferriprotoporphyrin IX hydroxide

B

56-54-2

quinidine

Conditions
ConditionsYield
In acetonitrile Equilibrium constant;

QUINIDINE Chemical Properties

Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent (Ia) in the heart. It has some synonyms like Quinidine free base; (+)-Quindine;6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol,etc.It is a stereoisomer of quinine, originally derived from the bark of the cinchona tree.It's white to light yellow crystal powder.

Molecular Formula: C20H24N2O2
Molecular Weight: 324.42
EINECS: 200-279-0
Melting point:  168-172 °C(lit.)
Alpha:  256 o(c=1, EtOH)
Water Solubility:  0.05 g/100 mL (20 °C)
Sensitive:  Light Sensitive
Merck:  14,8060
BRN:  91866

QUINIDINE Uses

Quinidine is a dextrorotatory stereoisomer of Quinine,usually used for antiarrhythmic (class IA) and  antimalarial purpose.Intravenous quinidine is also applicated for treatment of P. falciparum malaria.

QUINIDINE Toxicity Data With Reference

1.   

skn-rbt 3% MLD

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 137 (1962),410.
2.   

orl-rat LD50:263 mg/kg

   ARZNAD    Arzneimittel-Forschung. Drug Research. 27 (1977),589.
3.   

ivn-rat LD50:23 mg/kg

   JPETAB    Journal of Pharmacology and Experimental Therapeutics. 128 (1960),22.
4.   

orl-mus LD50:535 mg/kg

   JPETAB    Journal of Pharmacology and Experimental Therapeutics. 105 (1952),291.
5.   

ipr-mus LD50:135 mg/kg

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 137 (1962),410.
6.   

scu-mus LDLo:400 mg/kg

   AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 205 (1948),129.
7.   

ivn-mus LD50:53,600 µg/kg

   JMCMAR    Journal of Medicinal Chemistry. 27 (1984),1142.
8.   

ims-mus LD50:200 mg/kg

   27ZIAQ    Drug Dosages in Laboratory Animals-A Handbook C.D. Barnes andL.G. Eltherington,Berkeley, CA.: Univ. of California Press,1973,232.

RTECS:  VA4725000

QUINIDINE Consensus Reports

Reported in EPA TSCA Inventory.

QUINIDINE Safety Profile

Poison by ingestion, subcutaneous, intravenous, intramuscular, and intraperitoneal routes. A skin irritant. Implicated in aplastic anemia. When heated to decomposition it emits toxic fumes of NOx.

Hazard Codes:  Xn
Risk Statements:  22-20/21/22
Safety Statements:  36-22
RIDADR:  UN 2811 6.1/PG 3 
WGK: Germany  3
F:  8
HazardClass:  6.1(b)
PackingGroup:  III
Hazardous Substances Data: 56-54-2(Hazardous Substances Data)

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