Ampyzine

Ampyzine is a central nervous system stimulant.[1]

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 Y
  • Key:UUINNXPPLPDRQX-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Titled as a "Euphoriant" in the patent.[2] It can be used on belligerent cats (e.g. Caracals) to cause a marked increase in contentment and socialability.

Synthesis

The classical synthetic method for constructing 2-aminopyrazines is illustrated by the synthesis of ampyzine.

The condensation between glyoxal and 2-aminomalonamide [62009-47-6] gives 3-Hydroxypyrazine-2-carboxamide [55321-99-8] (1). Acid catalyzed hydrolysis of the amide gives 3-hydroxypyrazine-2-carboxylic acid [20737-42-2] (2); oxidative decarboxylation gives 2-hydroxypyrazine [6270-63-9] (3). Halogenation with PCl5 produces 2-chloropyrazine [14508-49-7] (4). Displacement of the leaving group by dimethylamine completes the synthesis of ampyzine (5).

See also
  • Triampyzine
  • Modaline

References
  1. Lednicer D, Mitscher LA (1980-05-13). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. ISBN 9780471043928.
  2. GB1019219 idem Emele Jane Frances, Wilson B Lutz, U.S. patent 3,249,503 (1966 to Warner Lambert Pharmaceutical).
  3. Cheeseman, G. W. H. (1960). "47. The synthesis and tautomerism of some 2-substituted pyrazines". Journal of the Chemical Society (Resumed): 242. doi:10.1039/JR9600000242.
  4. Muehlmann, Frank L. (1956). "Metabolite Analogs. V. Preparation of Some Substituted Pyrazines and Imidazo [b]pyrazines". Journal of the American Chemical Society 78 (1): 242–244. doi:10.1021/ja01582a066.
  5. Klein, Bernard; O'Donnell, Eileen; Auerbach, Joseph (1967). "Pyrazines. V. The amination of chloropyrazines and chloropyrazine N-oxide". The Journal of Organic Chemistry. 32 (8): 2412–2416. doi:10.1021/jo01283a012.
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