QUINIDINE supplier | CasNO.56-54-2

Name
Quinidine
EINECS 200-279-0
CAS No. 56-54-2
Article Data58
CAS DataBase
Density 1.218 g/cm³
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
Hazard Symbols Xn
Synonyms Quinidine(8CI);(+)-Quinidine;(8R,9S)-Quinidine;Chinidin;Conchinin;Conchinine;Kinidin;Pitayin;Pitayine;b-Quinidine;b-Quinine;
PSA 45.59000
LogP 3.11110

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
quininone;

...Expand

quininone: quininone

A: 56-54-2
quinidine

B: 130-95-0
Quinine

Conditions

Conditions	Yield
With ethanol; sodium ethanolate; aluminium

: 71-41-0
pentan-1-ol

: 130-95-0
Quinine

KOH: KOH

A: 56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2
9-epiquinine

B: 56-54-2
quinidine

C: 56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2
quinine

...Expand

: 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

A: 56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2
9-epiquinine

B: 56-54-2
quinidine

C: 130-95-0
Quinine

D: 56-54-2, 130-95-0, 572-59-8, 572-60-1, 42151-59-7, 47342-58-5, 72402-50-7, 72402-51-8, 72402-52-9, 72402-53-0, 101143-86-6, 101143-87-7, 101143-88-8, 146925-10-2
quinine

...Expand

: 110-86-1
pyridine

: C59H60FeN7O6

A: 25875-12-1
Fe(protoporphyrin-IX)(pyridine)2(1+)

B: 56-54-2
quinidine

Conditions

Conditions	Yield
In acetonitrile Equilibrium constant;

...Expand

: C54H55FeN6O6

: 15489-90-4
ferriprotoporphyrin IX hydroxide

B: 56-54-2
quinidine

Conditions

Conditions	Yield
In acetonitrile Equilibrium constant;

: C26H36N2O3Si

: 56-54-2
quinidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanesulfonamide; AD-mix-α / water; tert-butyl alcohol / 17 h / 20 °C 2.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.2: 6 h / 0 - 20 °C / Inert atmosphere 2.3: 0.5 h / 20 °C / Inert atmosphere 3.1: cesium fluoride / N,N-dimethyl-formamide; tert-butyl alcohol / 12 h / 110 °C View Scheme

: 946491-91-4
(3R,4S)-4-[(2S,3S)-2,3-Dihydroxy-3-(6-methoxy-quinolin-4-yl)-propyl]-3-vinyl-piperidine-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 56-54-2
quinidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Trimethyl orthoacetate; pyridinium p-toluenesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere 1.2: 6 h / 0 - 20 °C / Inert atmosphere 1.3: 0.5 h / 20 °C / Inert atmosphere 2.1: cesium fluoride / N,N-dimethyl-formamide; tert-butyl alcohol / 12 h / 110 °C View Scheme

: 100-44-7
benzyl chloride

: 56-54-2
quinidine

: 345217-88-1
9-O-benzylquinidine

Conditions

Conditions	Yield
Stage #1: quinidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;	100%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;	96%
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 20h;

: 536-38-9
4-chlorobenzoylmethyl bromide

: 56-54-2
quinidine

: C28H30ClN2O3(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	100%

: 619-41-0
4-(bromoacetyl)toluene

: 56-54-2
quinidine

: C29H33N2O3(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	99%

: 2632-13-5
2-Bromo-4'-methoxyacetophenone

: 56-54-2
quinidine

: C29H33N2O4(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	99%

: 100-39-0
benzyl bromide

: 56-54-2
quinidine

: 131042-95-0
(1S,2R,4S,5R)-1-benzyl-2-((S)-hydroxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

Conditions

Conditions	Yield
In acetone at 60℃; for 4h;	98%

: 70-11-1
α-bromoacetophenone

: 56-54-2
quinidine

: C28H31N2O3(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran for 72h;	98%
In tetrahydrofuran Inert atmosphere;	89%

: 32247-96-4
3,5-bis(trifluoromethyl)benzyl bromide

: 56-54-2
quinidine

: 945732-76-3
N-[3,5-bis(trifluoromethyl)benzyl]quinidinium bromide

Conditions

Conditions	Yield
In acetone at 60℃; for 4h;	97%
In toluene at 80℃; Inert atmosphere;	85%
In toluene at 80℃; for 12h;	85%
In toluene at 80℃;
In toluene at 80℃;

: 2-[3,5-bis(4-tert-butylphenyl)phenyl]-4,6-dichloro-5-phenylpyrimidine

: 56-54-2
quinidine

: C76H80N6O4

Conditions

Conditions	Yield
With potassium hydroxide In toluene for 2h; Dean-Stark; Reflux;	97%

: 62938-08-3
3,5-di-tert-butylbenzyl bromide

: 56-54-2
quinidine

: C35H47N2O2(1+)*Br(1-)

Conditions

Conditions	Yield
In acetone at 60℃; for 4h;	97%

: 4,6-dichloro-2-(2-methoxyphenyl)-5-phenylpyrimidine

: 56-54-2
quinidine

: C57H58N6O5

Conditions

Conditions	Yield
With potassium hydroxide In toluene for 2h; Dean-Stark; Reflux;	96%

: 22115-41-9
2-(bromomethyl)benzonitrile

: 56-54-2
quinidine

: C28H30N3O2(1+)*Br(1-)

Conditions

Conditions	Yield
In acetone at 60℃; for 4h;	96%
With sodium iodide In tetrahydrofuran at 20℃; Reflux;

: 56-54-2
quinidine

: 1435-55-8
dihydroquinidine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 2280.15 Torr; for 5h;	95%
With palladium 10% on activated carbon; hydrogen In methanol under 2280.15 Torr; for 5h;	92%
With hydrogenchloride; hydrogen; palladium dichloride

: 52289-93-7
2-methoxybenzyl bromide

: 56-54-2
quinidine

: Br(1-)*C28H33N2O3(1+)

Conditions

Conditions	Yield
In acetone at 60℃; for 4h;	95%
With sodium iodide In tetrahydrofuran at 20℃; Reflux;

: 151955-32-7
1-chloro-4-(9-O-dihydroquinidinyl)phthalazine

: 56-54-2
quinidine

: 188816-43-5
1-(9-O-quinidinyl)-4-(9-O-dihydroquinidinyl)phthalazine

Conditions

Conditions	Yield
With potassium hydroxide; potassium carbonate In toluene for 10h; 32;	93%

: 56-54-2
quinidine

: 4-((S)-hydroxy((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-ol

Conditions

Conditions	Yield
Stage #1: quinidine With boron tribromide In dichloromethane at -78 - 40℃; Inert atmosphere; Stage #2: With ammonium hydroxide; water In dichloromethane at 0℃;	93%
With sodium thioethylate In N,N-dimethyl-formamide at 110℃; for 6h; Inert atmosphere;	79%
With boron tribromide In dichloromethane at -78℃; Inert atmosphere; Reflux;	78%

: 56-54-2
quinidine

: 74-88-4
methyl iodide

: 577782-70-8
(1S,4S,5R)-2-((S)-methoxy(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidine

Conditions

Conditions	Yield
Stage #1: quinidine With potassium hydride In N,N-dimethyl-formamide; mineral oil; pentane at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil; pentane at 0 - 20℃; for 2h; Inert atmosphere;	93%
Stage #1: quinidine With potassium hydride In tetrahydrofuran at 0 - 50℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	86%
Stage #1: quinidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃;	56%
Stage #1: quinidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h; Schlenk technique; Inert atmosphere;	41%
Stage #1: quinidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 50℃; for 2.5h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 24h; Inert atmosphere; Schlenk technique;	32%

: 4,6-dichloro-2-(3,5-diphenylphenyl)-5-phenylpyrimidine

: 56-54-2
quinidine

: C68H64N6O4

Conditions

Conditions	Yield
With potassium hydroxide In toluene for 2h; Dean-Stark; Reflux;	92%

: 16588-74-2
3,5-ditrifluoromethylisocyanate

: 56-54-2
quinidine

: 9-O-(3,5-bis(trifluoromethyl)phenylcarbamate)quinidine

Conditions

Conditions	Yield
In dichloromethane at 0℃; for 2h; Inert atmosphere;	92%

: 37942-07-7
3,5-di-tert-butyl-2-hydroxybenzaldehyde

: 56-54-2
quinidine

: C35H45N3O2

Conditions

Conditions	Yield
With magnesium sulfate In ethanol for 5h; Reflux;	90%

: 56-54-2
quinidine

: 139237-97-1
(S)-4-((1S,2R,4S,5Z/E)-5-ethylidene-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-methoxyquinoline

Conditions

Conditions	Yield
Stage #1: quinidine With sulfuric acid In ethanol at 20℃; for 0.166667h; Stage #2: With rhodium(III) chloride trihydrate In ethanol Reflux;	88%

: 402-49-3
4-bromomethyltrifluoromethylbenzene

: 56-54-2
quinidine

: N-(4-trifluoromethylbenzyl)quinidinium bromide

Conditions

Conditions	Yield
In toluene at 80℃; Inert atmosphere;	87%
In toluene at 80℃; for 12h;	87%
In tetrahydrofuran Heating;

: 106-95-6
allyl bromide

: 56-54-2
quinidine

: C23H28N2O2

Conditions

Conditions	Yield
Stage #1: quinidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;	87%

: 1079-66-9
chloro-diphenylphosphine

: 56-54-2
quinidine

A: (9S)-6'-methoxycinchonan-9-yl diphenylphosphinite

B: Diphenyl-phosphinic acid (S)-(6-methoxy-quinolin-4-yl)-((1S,2R,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h;	A 86% B n/a

...Expand

: 67385-09-5
2-[(tert-butoxycarbonyl)amino]-1-ethanethiol

: 56-54-2
quinidine

: tert‐butyl N‐[2‐({3‐[(1S,3R,4S,6R)‐6‐[(S)‐hydroxy(6‐methoxyquinolin‐4‐yl)methyl]‐1‐azabicyclo[2.2.2]octan‐3‐yl]propyl}sulfanyl)ethyl]carbamate

Conditions

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In chloroform for 0.166667h; Irradiation;	86%
In neat (no solvent) at 80℃; for 60h; Sealed tube; Inert atmosphere;	25%

: 201230-82-2
carbon monoxide

: 56-54-2
quinidine

: 10,11-dihydroquinidine-11-carbaldehyde

Conditions

Conditions	Yield
With [(2,4-di-t-Bu-C6H3-O)2POCH2]4C; hydrogen; acetylacetonatodicarbonylrhodium(l) In toluene at 90℃; under 15001.5 Torr;	85%

: 1765-40-8
(bromomethyl)pentafluorobenzene

: 56-54-2
quinidine

: 231303-52-9
N-(2,3,4,5,6-pentafluorobenzyl)quinidinium bromide

Conditions

Conditions	Yield
In toluene at 80℃; for 12h;	83%

: 56-54-2
quinidine

: quinidine 1'-oxide

Conditions

Conditions	Yield
Stage #1: quinidine With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 3h; pH=10; Inert atmosphere; Stage #2: With sulphurous acid In acetone at 0 - 20℃; pH=8; Inert atmosphere;	83%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 3.5h; Cooling with ice;	83%
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 3 h / 0 - 20 °C 2: sodium hydrogensulfite; hydrogenchloride / water; acetone / 12 h / 0 - 20 °C View Scheme

: 98-59-9
p-toluenesulfonyl chloride

: 56-54-2
quinidine

: 112661-57-1
O-tosylquinidine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran for 9h; Heating;	82%
With tributyl-amine; potassium hydroxide In dichloromethane; water at 20℃;	76%
With sodium hydroxide; benzene

: 876-08-4
p-(chloromethyl)benzoyl chloride

: 56-54-2
quinidine

: C28H29ClN2O3

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; acetonitrile at 20℃; for 16h;	82%

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 NO_x.

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)

Product Name

Quinidine

Synthetic route

QUINIDINE Chemical Properties

QUINIDINE Uses

QUINIDINE Toxicity Data With Reference

QUINIDINE Consensus Reports

QUINIDINE Safety Profile

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