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Merck
CN

160393

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849867
EC Number:
200-560-8
Beilstein/REAXYS Number:
3812133
MDL number:
MFCD00013166

Key Documents

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Product Name

Primaquine bisphosphate, 98%

form

powder

InChI key

GJOHLWZHWQUKAU-UHFFFAOYSA-N

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)

SMILES string

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

assay

98%

mp

205-206 °C (dec.) (lit.)

solubility

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

functional group

amine
phosphate

Quality Level

100

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX7208
MKCV7273
MKCR2724
MKCM9310
MKCH6744

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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
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
Melanie Lödige et al.
International journal of medical microbiology : IJMM, 303(8), 539-547 (2013-09-03)
We present a new class of hybrid molecules consisting of the established antiplasmodial drugs primaquine and chloroquine. No drug is known to date that acts comparably against all stages of Plasmodium in its life cycle. Starting from available precursors, we
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
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
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