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Substance Name: Primaquine phosphate [USP]
RN: 63-45-6
UNII: H0982HF78B
InChIKey: GJOHLWZHWQUKAU-UHFFFAOYSA-N

Note

  • An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)

Molecular Formula

  • C15-H21-N3-O.2H3-O4-P

Molecular Weight

  • 455.3383
 

Classification Codes

  • Antimalarial
  • Drug / Therapeutic Agent
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Primaquine phosphate [USP]

Synonyms

  • (+-)-8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline phosphate (1:2)
  • 1,4-Pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, (+-)-, phosphate (1:2)
  • 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline diphosphate
  • 8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline phosphate (1:2)
  • CCRIS 1946
  • EINECS 200-560-8
  • NSC 149765
  • Primaquine diphosphate
  • Primaquine phosphate
  • UNII-H0982HF78B

Systematic Names

  • 1,4-Pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, phosphate (1:2)
  • 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)-, phosphate (1:2) (9CI)
  • Primaquine bis(phosphate)
  • Primaquine diphosphate
  • Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, phosphate (1:2)

Registry Numbers

CAS Registry Number

  • 63-45-6

FDA UNII

  • H0982HF78B

Related Registry Number

  • 90-34-6 (Parent)

System Generated Number

  • 0000063456

Molecular Formulas

Molecular Formula

  • C15-H21-N3-O.2H3-O4-P

Molecular Formula Fragments

  • C15-H21-N3-O
  • COMPONENT
  • H3-O4-P

Structure Descriptors

InChI

InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)

InChIKey

GJOHLWZHWQUKAU-UHFFFAOYSA-N

Smiles

COc1cc(NC(C)CCCN)c2ncccc2c1.OP(=O)(O)O.OP(=O)(O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - domestic LD50 intravenous 19300ug/kg (19.3mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
mouse LD50 intraperitoneal 105mg/kg (105mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1775, 1970.
mouse LD50 oral 68mg/kg (68mg/kg)   Transactions of the Royal Society of Tropical Medicine and Hygiene. Vol. 74, Pg. 43, 1980.
rat LD50 oral 177mg/kg (177mg/kg)   Journal of Medicinal Chemistry. Vol. 32, Pg. 1728, 1989.