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Sigma-Aldrich

Primaquine bisphosphate

98%

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Synonym(s):
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline diphosphate salt, Primaquine diphosphate salt
Empirical Formula (Hill Notation):
C15H21N3O · 2H3PO4
CAS Number:
63-45-6
Molecular Weight:
455.34
Beilstein:
3812133
EC Number:
200-560-8
MDL number:
MFCD00013166
UNSPSC Code:
12352100
PubChem Substance ID:
24849867
NACRES:
NA.22

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H301,H341,H361fd

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
Stefan Hoyer et al.
PloS one, 7(10), e45797-e45797 (2012-10-11)
Recent studies have shown that Plasmodium falciparum malaria parasites in Pailin province, along the border between Thailand and Cambodia, have become resistant to artemisinin derivatives. To better define the epidemiology of P. falciparum populations and to assess the risk of
Alice C Eziefula et al.
Malaria journal, 11, 360-360 (2012-11-08)
Following the recent successes of malaria control in sub-Saharan Africa, the gametocytocidal drug primaquine needs evaluation as a tool to further reduce the transmission of Plasmodium falciparum malaria. The drug has scarcely been used in Africa because of concerns about
Issahy Cano et al.
Frontiers in cell and developmental biology, 9, 734346-734346 (2021-10-08)
Galectin-3 (Gal3) is a carbohydrate-binding protein reported to promote angiogenesis by influencing vascular endothelial growth factor-A receptor 2 (VEGFR2) signal transduction. Here we evaluated whether the ability of Gal3 to function as an angiogenic factor involved vascular endothelial growth factor
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