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Substance Name: Primaquine [INN:BAN]
RN: 90-34-6
UNII: MVR3634GX1
InChIKey: INDBQLZJXZLFIT-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

Molecular Weight

  • 259.3509
 

Classification Codes

  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Mutation Data

Names and Synonyms

Name of Substance

  • Primaquine
  • Primaquine [INN:BAN]

MeSH Heading

  • Primaquine

Synonyms

  • 4-22-00-05817 (Beilstein Handbook Reference)
  • 6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
  • 8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
  • BRN 0019337
  • CCRIS 4109
  • EINECS 201-987-2
  • HSDB 6516
  • Neo-Quipenyl
  • NSC 27296
  • Primachin
  • Primachina
  • Primachina [DCIT]
  • Primachinum
  • Primaquin
  • Primaquina
  • Primaquina [INN-Spanish]
  • Primaquine
  • Primaquinum
  • Primaquinum [INN-Latin]
  • Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy
  • S. N. 13272
  • SN 13,272
  • UNII-MVR3634GX1
  • WR 2975

Systematic Names

  • 1,4-Pentanediamine, N4-(6-methoxy-8-quinolinyl)- (9CI)
  • Primaquine
  • Quinoline, 8-(4-amino-1-methylbutylamino)-6-methoxy-

Registry Numbers

CAS Registry Number

  • 90-34-6

FDA UNII

  • MVR3634GX1

Related Registry Number

  • 63-45-6 (1:2 PO4)

System Generated Number

  • 0000090346

Structure Descriptors

InChI

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

InChIKey

INDBQLZJXZLFIT-UHFFFAOYSA-N

Smiles

CC(CCCN)Nc1cc(cc2c1nccc2)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
monkey LDLo oral 96mg/kg (96mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Antibiotics and Chemotherapy Vol. 12, Pg. 103, 1962.
mouse LD50 intravenous 15900ug/kg (15.9mg/kg)   Antibiotics and Chemotherapy Vol. 12, Pg. 103, 1962.
mouse LD50 oral 100mg/kg (100mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 12, Pg. 51, 1977.
mouse LD50 unreported 68800ug/kg (68.8mg/kg)   Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 16, Pg. 502, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 3.150 (none)   EST
Atmospheric OH Rate Constant 2.47E-10 cm3/molecule-sec 25 EST

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