Ampyzine

Last updated
Ampyzine
Ampyzine.svg
Clinical data
ATC code
  • none
Identifiers
  • N,N-Dimethylpyrazin-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C6H9N3
Molar mass 123.159 g·mol−1
3D model (JSmol)
  • n1ccnc(N(C)C)c1
  • InChI=1S/C6H9N3/c1-9(2)6-5-7-3-4-8-6/h3-5H,1-2H3 Yes check.svgY
  • Key:UUINNXPPLPDRQX-UHFFFAOYSA-N Yes check.svgY

Ampyzine is a central nervous system stimulant. [1]

Synthesis

Ampyzine-synthesis.svg

The classical method for synthesizing 2-aminopyrazines is illustrated by the synthesis of ampyzine. The condensation reaction between glyoxal and 2-aminomalonamide forms the pyrazine derivative (1). Acid-catalysed hydrolysis of the amide and decarboxylation gives 2-hydroxypyrazine (3). Halogenation with phosphorus pentachloride produces 2-chloropyrazine (4) which reacts with dimethylamine to yield ampyzine. [1] [2]

Contents

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References

  1. 1 2 Lednicer D, Mitscher LA (1980-05-13). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. ISBN   9780471043928.
  2. Emele Jane Frances, Wilson B Lutz, U.S. patent 3,249,503 (1966 to Warner Lambert Pharmaceutical).