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Substance Name: Mepacrine [INN:BAN]
RN: 83-89-6
UNII: H0C805XYDE
InChIKey: GPKJTRJOBQGKQK-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  • An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years.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

Molecular Weight

  • 399.963
 

Classification Codes

  • Anthelmintics
  • Anti-Infective Agents
  • Anticestodal Agents
  • Antimalarials
  • Antinematodal Agents
  • Antineoplastic Agents
  • Antiparasitic Agents
  • Antiplatyhelmintic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Mepacrine [INN:BAN]
  • Quinacrine

MeSH Heading

  • Quinacrine

Synonyms

  • 2-Methoxy-6-chloro-9-diethylaminopentylaminoacridine
  • 3-Chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine
  • 6-Chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine
  • Acrichine
  • Acrinamine
  • Acriquine
  • AI3-04467
  • Akrichin
  • Antimalarina
  • Atabrine
  • CCRIS 3726
  • CCRIS 8633
  • EINECS 201-508-7
  • Erion
  • Haffkinine
  • HSDB 3253
  • Italchine
  • Mepacrina
  • Mepacrina [INN-Spanish]
  • Mepacrine
  • Mepacrinum
  • Mepacrinum [INN-Latin]
  • Quinacrine
  • Quinactine
  • ST 439
  • UNII-H0C805XYDE

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 83-89-6

FDA UNII

  • H0C805XYDE

Other Registry Number

  • 66777-81-9

Related Registry Numbers

  • 130-42-7 (mono-hydrochloride)
  • 316-05-2 (dimesylate)
  • 6151-30-0 (di-hydrochloride, di-hydrate)
  • 69-05-6 (di-hydrochloride)
  • 78901-94-7 (monoacetate)

System Generated Number

  • 0000083896

Structure Descriptors

InChI

1S/C23H30ClN3O/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)

InChIKey

GPKJTRJOBQGKQK-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 10mg/kg (10mg/kg)   Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
chicken LDLo oral 714mg/kg (714mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 201, Pg. 402, 1943.
mouse LD50 intravenous 50mg/kg (50mg/kg)   Therapie. Vol. 25, Pg. 823, 1970.
mouse LD50 oral 1320mg/kg (1320mg/kg)   Fortschritte der Arzneimittelforschung. Progress in Drug Research. Vol. 17, Pg. 108, 1973.
mouse LD50 subcutaneous 239mg/kg (239mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.
rabbit LD50 intravenous 8mg/kg (8mg/kg)   Therapie. Vol. 25, Pg. 823, 1970.
rabbit LD50 subcutaneous 75mg/kg (75mg/kg)   Therapie. Vol. 25, Pg. 823, 1970.
rabbit LDLo oral 400mg/kg (400mg/kg)   Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
women TDLo oral 75mg/kg/5D-I (75mg/kg) BEHAVIORAL: WAKEFULNESS

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Mayo Clinic Proceedings. Vol. 64, Pg. 129, 1989.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 5.750 (none)   EST
Atmospheric OH Rate Constant 3.20E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.