Ampyzine Explained

Ampyzine, also known as dimethylaminopyrazine or as ampyzine sulfate in the case of the sulfate salt (developmental code name W-3580B), is a drug described as a "central stimulant" or "CNS stimulant" and "euphoriant".^{[1] [2]} It is said to be a monoamine oxidase inhibitor (MAOI).^[3] Ampyzine was first described in the scientific literature by 1960.

An analogue of ampyzine is triampyzine (3,5,6-trimethylampyzine; developmental code name W-3976B).^[4] This drug is described as an anticholinergic and antisecretory agent.

Synthesis

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.^{[5] [6] [7]}

Notes and References

1. Book: Elks, J. . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer US . 2014 . 978-1-4757-2085-3 . 7 October 2024 . 436.
2. Book: Milne, G.W.A. . Drugs: Synonyms and Properties . Taylor & Francis . Routledge Revivals . 2018 . 978-1-351-78990-5 . 7 October 2024 . 547.
3. Book: Effron, D.H. . Psychotropic Drugs and Related Compounds . National Institute of Mental Health . DHEW publication . 1972 . 7 October 2024 . 202.
4. Book: Milne, G.W.A. . Drugs: Synonyms and Properties . Wiley . 2002 . 978-0-566-08491-1 . 7 October 2024 . 220.
5. Book: The Organic Chemistry of Drug Synthesis. 9780471043928. Lednicer D, Mitscher LA . 1980-05-13. John Wiley & Sons .
6. Miller . William . Investigational Drugs . American Journal of Health-System Pharmacy . Oxford University Press (OUP) . 23 . 12 . 1 December 1966 . 1079-2082 . 10.1093/ajhp/23.12.683 . 683–687.
7. Emele Jane Frances, Wilson B Lutz, (1966 to Warner Lambert Pharmaceutical).