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Sigma-Aldrich

Primaquine bisphosphate

98%

Synonym(s):

8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline diphosphate salt, Primaquine diphosphate salt

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About This Item

Empirical Formula (Hill Notation):
C15H21N3O · 2H3PO4
CAS Number:
63-45-6
Molecular Weight:
455.34
Beilstein/REAXYS Number:
3812133
EC Number:
200-560-8
MDL number:
MFCD00013166
UNSPSC Code:
12352100
PubChem Substance ID:
24849867
NACRES:
NA.22

assay

98%

form

powder

mp

205-206 °C (dec.) (lit.)

solubility

water: soluble 50 mg/mL, clear, orange to red

SMILES string

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

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)

InChI key

GJOHLWZHWQUKAU-UHFFFAOYSA-N

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Application

Primaquine bisphosphate was used in the colorimetric microplate-based, room temperature assay to determine the urea synthesis in cell culture. It was also used in the preparation of primaquine, an established antiplasmodial drug.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Muta. 2 - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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N P Dhammika Nanayakkara et al.
Antimicrobial agents and chemotherapy, 52(6), 2130-2137 (2008-04-02)
8-Aminoquinolines are an important class of antiparasitic agents, with broad utility and excellent efficacy, but also limitations due to hematological toxicities, primarily methemoglobinemia and hemolysis. One representative from this class, (+/-)-8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3,4-dichlorophenoxy]quinoline succinate (NPC1161C), proved extremely efficacious in animal models of
Robert J X Zawada et al.
Biochemistry and cell biology = Biochimie et biologie cellulaire, 87(3), 541-544 (2009-05-19)
Urea is the major nitrogenous end product of protein metabolism in mammals. Here, we describe a quantitative, sensitive method for urea determination using a modified Jung reagent. This assay is specific for urea and is unaffected by ammonia, a common
Annemarie Voorberg-van der Wel et al.
PloS one, 8(1), e54888-e54888 (2013-01-30)
A major challenge for strategies to combat the human malaria parasite Plasmodium vivax is the presence of hypnozoites in the liver. These dormant forms can cause renewed clinical disease after reactivation through unknown mechanisms. The closely related non-human primate malaria
Manojit Roy et al.
PLoS neglected tropical diseases, 7(1), e1979-e1979 (2013-01-18)
With over a hundred million annual infections and rising morbidity and mortality, Plasmodium vivax malaria remains largely a neglected disease. In particular, the dependence of this malaria species on relapses and the potential significance of the dormant stage as a
Nicholas J White
The Lancet. Infectious diseases, 13(2), 175-181 (2012-11-28)
Falciparum malaria is transmitted by anopheline mosquitoes that have fed on blood containing gametocytes of Plasmodium falciparum. In areas of low malaria transmission, where symptomatic infections contribute substantially to malaria transmission, the use of gametocytocidal drugs reduces the incidence of
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