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Substance Name: Quinacrine hydrochloride
RN: 69-05-6
UNII: 81A613ZZ6X
InChIKey: UDKVBVICMUEIKS-UHFFFAOYSA-N

Note

  • An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.

Molecular Formula

  • C23-H30-Cl-N3-O.2Cl-H

Molecular Weight

  • 472.8848
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Results Name

  • Quinacrine hydrochloride

Name of Substance

  • Quinacrine hydrochloride
  • Quinacrine hydrochloride anhydrous

Synonyms

  • 2-Chloro-5-(omega-diethylamino-alpha-methylbutylamino)-7-methoxyacridine dihydrochloride
  • 2-Methoxy-6-chloro-9-(4-diethylamino-1-methylbutylamino)acridine dihydrochloride
  • 3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine dihydrochloride
  • 3-Chloro-9-(4'-diethylamino-1'-methylbutylamino)-7-methoxyacridine dihydrochloride
  • 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine dihydrochloride
  • 866 R.P.
  • Atabrine dihydrochloride
  • Atabrine hydrochloride
  • Atebrin hydrochloride
  • Atebrine
  • CCRIS 4709
  • Chemiochin
  • Chinacrin hydrochloride
  • Crinodora
  • EINECS 200-700-8
  • Erion
  • Italchin
  • Malaricida
  • Mecryl
  • Mepacrine dihydrochloride
  • Mepacrine hydrochloride
  • Methoquine
  • Metochin
  • Metoquin
  • Metoquine
  • NSC 14229
  • Palacrin
  • Palusan
  • Pentilen
  • Quinacrine dihydrochloride
  • Quinacrine HCl
  • Quinacrine hydrochloride
  • S.N. 390
  • SN 390
  • UNII-81A613ZZ6X

Systematic Names

  • 1,4-Pentanediamine, N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-, dihydrochloride
  • Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-, dihydrochloride
  • Mepacrine hydrochloride
  • Quinacrine dihydrochloride

Registry Numbers

CAS Registry Number

  • 69-05-6

FDA UNII

  • 81A613ZZ6X

Other Registry Number

  • 133347-98-5

Related Registry Number

  • 83-89-6 (Parent)

System Generated Number

  • 0000069056

Molecular Formulas

Molecular Formula

  • C23-H30-Cl-N3-O.2Cl-H

Molecular Formula Fragments

  • C23-H30-Cl-N3-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C23H30ClN3O.2ClH/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H

InChIKey

UDKVBVICMUEIKS-UHFFFAOYSA-N

Smiles

CCN(CC)CCCC(C)Nc1c2ccc(cc2nc3c1cc(cc3)OC)Cl.Cl.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 10mg/kg (10mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
cat LDLo oral 200mg/kg (200mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
cat LDLo subcutaneous 100mg/kg (100mg/kg) LIVER: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 170, Pg. 328, 1933.
dog LDLo intravenous 20mg/kg (20mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

VASCULAR: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 34, Pg. 20, 1945.
gerbil LDLo intraperitoneal 70mg/kg (70mg/kg)   Contraception. Vol. 17, Pg. 231, 1978.
guinea pig LD50 intravenous 14mg/kg (14mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
hamster LDLo intraperitoneal 80mg/kg (80mg/kg)   Contraception. Vol. 17, Pg. 231, 1978.
man TDLo oral 34mg/kg/8D-I (34mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Southern Medical Journal. Vol. 75, Pg. 359, 1982.
monkey LDLo intravenous 15mg/kg (15mg/kg)   Contraception. Vol. 24, Pg. 269, 1981.
monkey LDLo intravenous 15mg/kg (15mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Contraception. Vol. 24, Pg. 269, 1981.
mouse LD50 intraperitoneal 189mg/kg (189mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 133, 1947.
mouse LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse LD50 oral 557mg/kg (557mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse LD50 subcutaneous 212mg/kg (212mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Annals of Biochemistry and Experimental Medicine. Vol. 1, Pg. 317, 1941.
rabbit LD50 intravenous 9mg/kg (9mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rabbit LD50 oral 433mg/kg (433mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat LD50 intrauterine 100mg/kg (100mg/kg)   Indian Journal of Experimental Biology. Vol. 16, Pg. 1074, 1978.
rat LD50 intravenous 29mg/kg (29mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat LD50 oral 660mg/kg (660mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
women TDLo oral 18mg/kg/3D-I (18mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Southern Medical Journal. Vol. 75, Pg. 359, 1982.