2,4-Diamino-6-hydroxypyrimidine

Names

[ CAS No. ]:
56-06-4

[ Name ]:
2,4-Diamino-6-hydroxypyrimidine

[Synonym ]:
2,6-diaminopyrimidin-4(3H)-one
2,6-Diaminopyrimidin-4-one
2,4-Diamino-6-hydroxypyrimidine
2,6-diaminopyrimidin-4-ol
4-Pyrimidinol, 2,6-diamino-
2,4-Diamino-6-hydroxy
2,6-diamino-4-hydroxy-pyrimidine
6-hydroxy-2,4-diaminopyrimidine
2,6-Diamino-4(1H)-pyrimidinone
AURORA KA-376
MFCD00006098
2,4-Diamino-6-pyrimidinone
2,6-Diaminopyrimidin-4(1H)-one
EINECS 200-254-4
2,4-diaminohypoxanthine
6-Aminoisocytosine
6-Hydroxy-2,4-pyrimidinediamine
DAHP
2,4-DIAMINO-6-HYDROXY PYRIMIDINE

Biological Activity

[Description]:

2,4-Diamino-6-hydroxypyrimidine is a specific GTP cyclohydrolase I inhibitor (the rate-limiting enzyme in de novo pterin synthesis), blocks BH4 synthesis and suppresses NO production[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[Target]

GTP cyclohydrolase I[1]

[References]

[1]. Sung YJ, et al. 2,4-Diamino-6-hydroxypyrimidine, an inhibitor of GTP cyclohydrolase I, suppresses nitric oxide production by chicken macrophages. Int J Immunopharmacol. 1994 Feb;16(2):101-8.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
524.0±53.0 °C at 760 mmHg

[ Melting Point ]:
285-286 °C (dec.)(lit.)

[ Molecular Formula ]:
C₄H₆N₄O

[ Molecular Weight ]:
126.12

[ Flash Point ]:
270.7±30.9 °C

[ Exact Mass ]:
126.054161

[ PSA ]:
98.05000

[ LogP ]:
-1.29

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.770

[ Storage condition ]:
Desiccate at +4°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29335995

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

GTP cyclohydrolase I: purification, characterization, and effects of inhibition on nitric oxide synthase in nocardia species.

Appl. Environ. Microbiol. 69(12) , 7507-7513, (2003)

GTP cyclohydrolase I (GTPCH) catalyzes the first step in pteridine biosynthesis in Nocardia sp. strain NRRL 5646. This enzyme is important in the biosynthesis of tetrahydrobiopterin (BH4), a reducing ...

Acute inhibition of guanosine triphosphate cyclohydrolase 1 uncouples endothelial nitric oxide synthase and elevates blood pressure.

Hypertension 52(3) , 484-90, (2008)

GTP cyclohydrolase 1 (GTPCH1) is the rate-limiting enzyme in de novo synthesis of tetrahydrobiopterin (BH4), an essential cofactor for endothelial NO synthase (eNOS) dictating, at least partly, the ba...

Attenuation of biopterin synthesis prevents Escherichia coli K1 invasion of brain endothelial cells and the development of meningitis in newborn mice.

J. Infect. Dis. 207(1) , 61-71, (2013)

Elevated levels of pterins and nitric oxide (NO) are observed in patients with septic shock and bacterial meningitis. We demonstrate that Escherichia coli K1 infection of human brain microvascular end...