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Substance Name: Pamaquine [INN]
RN: 491-92-9
UNII: 99QVL5KPSU
InChIKey: QTQWMSOQOSJFBV-UHFFFAOYSA-N

Classification Codes

  • Human Data
  • Mutation Data

Molecular Formula

  • C19-H29-N3-O

Molecular Weight

  • 315.4581
 
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Names and Synonyms

Name of Substance

  • Pamaquine
  • Pamaquine [INN]

Synonyms

  • 4-22-00-05818 (Beilstein Handbook Reference)
  • 8-((4-(Diethylamino)-1-methylbutyl)amino)-6-methoxyquinoline
  • Aminoquin
  • Beprochine
  • BRN 0027810
  • CCRIS 6979
  • Gamefar
  • NSC 167382
  • Pamaquin
  • Pamaquine
  • Plasmochin
  • Plasmocide
  • Plasmoquine
  • Praequine
  • Prequine
  • Quipenyl
  • Rhodoquine
  • UNII-99QVL5KPSU

Systematic Names

  • 1,4-Pentanediamine, N1,N1-diethyl-N4-(6-methoxy-8-quinolinyl)- (9CI)
  • N(1),N(1)-Diethyl-N(4)-(6-methoxy-8-quinolinyl)-1,4-pentanediamine
  • Pamaquine
  • Quinoline, 8-((4-(diethylamino)-1-methylbutyl)amino)-6-methoxy-

Registry Numbers

CAS Registry Number

  • 491-92-9

FDA UNII

  • 99QVL5KPSU

Related Registry Numbers

  • 5463-14-9 (mono-hydriodide)
  • 63680-62-6 (mono-hydrochloride)

System Generated Number

  • 0000491929

Structure Descriptors

InChI

1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3

InChIKey

QTQWMSOQOSJFBV-UHFFFAOYSA-N

Smiles

CCN(CC)CCCC(C)Nc1cc(OC)cc2cccnc12

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LDLo intramuscular 33mg/kg (33mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
bird - domestic LDLo oral 66mg/kg (66mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
cat LDLo intravenous 5mg/kg (5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

BEHAVIORAL: COMA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
cat LDLo oral 7500ug/kg (7.5mg/kg) BEHAVIORAL: COMA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
cat LDLo subcutaneous 5mg/kg (5mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

BEHAVIORAL: COMA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
chicken LDLo oral 57mg/kg (57mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 201, Pg. 402, 1943.
dog LDLo subcutaneous 20mg/kg (20mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
man LDLo unreported 7353ug/kg (7.353mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 oral 68mg/kg (68mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 6, Pg. 185, 1951.
mouse LDLo subcutaneous 12500ug/kg (12.5mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
rabbit LDLo intravenous 3500ug/kg (3.5mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.
rabbit LDLo oral 220mg/kg (220mg/kg)   Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 341, 1929.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 4.730 (none)   EST
Atmospheric OH Rate Constant 3.20E-10 cm3/molecule-sec 25 EST

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