pamaquine

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Names

[ CAS No. ]:
491-92-9

[ Name ]:
pamaquine

[Synonym ]:
Rhodoquine
Beprochine
Aminoquin
Prequine
Praequine
PAMAQUINE
Plasmocide
Pamaquin
Plasmochin
Plasmoquine

Chemical & Physical Properties

[ Molecular Formula ]:
C19H29N3O

[ Molecular Weight ]:
315.45300

[ Exact Mass ]:
315.23100

[ PSA ]:
37.39000

[ LogP ]:
4.23880

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VB4725000
CHEMICAL NAME :
Quinoline, 8-((4-(diethylamino)-1-methylbutyl)amino)-6-methoxy-
CAS REGISTRY NUMBER :
491-92-9
BEILSTEIN REFERENCE NO. :
0027810
LAST UPDATED :
199612
DATA ITEMS CITED :
14
MOLECULAR FORMULA :
C19-H29-N3-O
MOLECULAR WEIGHT :
315.51
WISWESSER LINE NOTATION :
T66 BNJ HO1 JMY1&3N2&2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7353 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
68 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
12500 ug/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
7500 ug/kg
TOXIC EFFECTS :
Behavioral - coma Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Behavioral - coma Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - coma Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
220 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
3500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - chicken
DOSE/DURATION :
57 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - domestic
DOSE/DURATION :
66 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Blood - methemoglobinemia-carboxyhemoglobin
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Bird - domestic
DOSE/DURATION :
33 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Blood - methemoglobinemia-carboxyhemoglobin

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria - Salmonella typhimurium
DOSE/DURATION :
1 mg/plate
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 325,7,1994

Synthetic Route

Precursor & DownStream

Precursor

  • 8-Amino-6-methoxyquinoline
  • 5-(Diethylamino)-2-pentanone
  • 4,4-DIETHOXY-1-(DIETHYLAMINO)PENTANE
  • Novoldiamine
  • N2-(4-diethylamino-1-methyl-butyl)-4-methoxy-o-phenylenediamine
  • Glycerol
  • N-(6-methoxyquinolin-8-yl)formamide
  • Ethyl formate
  • Methanol

DownStream

  • 6-Methoxy-8-quinolinol
  • Novoldiamine

Related Compounds

  • pamaquine
  • Pamaquine hydriodide
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • 2-chloro-N-((1-(2-methoxyethyl)piperidin-4-yl)methyl)benzenesulfonamide
  • 4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide