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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:
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

functional group

amine
phosphate

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7273
MKCR2724
MKCM9310
MKCH6744
MKCG0489

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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
Rosalind E Howes et al.
Advances in parasitology, 81, 133-201 (2013-02-07)
Glucose-6-phosphate dehydrogenase (G6PD) is a potentially pathogenic inherited enzyme abnormality and, similar to other human red blood cell polymorphisms, is particularly prevalent in historically malaria endemic countries. The spatial extent of Plasmodium vivax malaria overlaps widely with that of G6PD
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
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
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
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