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5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine

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5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine Basic information

Product Name:
5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine
Synonyms:
  • ORMETHOPRIM
  • ORMETOPRIM
  • ORMETOPRIN
  • OMP
  • 5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine
  • L-Ascorbic Phosphate Magnesium
  • 2,4-DiaMino-5-92-Methyl-4,5- diMethoxybenzyl)pyriMidine
  • DiaMino-5-(6-Methylveratryl)pyriMidine
CAS:
6981-18-6
MF:
C14H18N4O2
MW:
274.32
EINECS:
230-246-6
Product Categories:
  • Active Pharmaceutical Ingredients
  • Heterocycles
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
6981-18-6.mol
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5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine Chemical Properties

Melting point:
231.0 to 235.0 °C
Boiling point:
521.5±60.0 °C(Predicted)
Density 
1.223±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
form 
Solid
pka
7.11±0.10(Predicted)
color 
Off-White
Water Solubility 
Water: Insoluble
λmax
287nm(CHCl3)(lit.)
Stability:
Hygroscopic
CAS DataBase Reference
6981-18-6(CAS DataBase Reference)
EPA Substance Registry System
Ormetoprim (6981-18-6)
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Safety Information

Safety Statements 
24/25
HS Code 
29333990
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5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine Usage And Synthesis

Uses

It is a potent and selective inhibitor of bacterial dihydrofolate reductase, the enzyme responsible for the NADPH-dependent reduction of 7,8-dihydrofolate to 5,6,7,8-tetrahydrofolate. Antibacterial.This compound is a contaminant of emerging concern (CECs).

Definition

ChEBI: 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine is a dimethoxybenzene.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 14, p. 462, 1971 DOI: 10.1021/jm00287a029

in vivo

Ormetoprim (8.3 mg/kg; i.p.) exhibits absorption half-life (5.4 h), elimination half-life (7.5 h) and Cmax (1.2±0.2 μg/mL)[3].
Ormetoprim (8.3 mg/kg; p.o.) exhibits absorption half-life (3.9 h), elimination half-life (3.9 h), Cmax (1.6±0.4 μg/mL) and oral availability (78.5%) relative to intraperitoneal administration[3].

Animal Model:Hybrid striped bass (565-805 g)[3]
Dosage:50 mg/kg Sulfadimethoxine and Ormetoprim in a 5:1 ratio (Pharmacokinetic Analysis)
Administration:I.p. and p.o. administration
Result:I.p.: t1/2(elim)=7.5 h; t1/2(abs)=5.4 h; Cmax=1.2 μg/mL.
P.o.: t1/2(elim)=3.9 h; t1/2(abs)=3.9 h; Cmax=1.6 μg/mL; F=78.5%.

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