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Ampyzine

From Wikipedia, the free encyclopedia
Ampyzine
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
FormulaC6H9N3
Molar mass123.159 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 checkY
  • Key:UUINNXPPLPDRQX-UHFFFAOYSA-N checkY

Ampyzine is a central nervous system stimulant.[1]

Synthesis[edit]

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]

References[edit]

  1. ^ a b 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).

External links[edit]

  • Media related to Ampyzine at Wikimedia Commons