Chemistry:Ampyzine

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Ampyzine (INN), also known as dimethylaminopyrazine or as ampyzine sulfate (USAN) 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.[1]

An analogue of ampyzine is triampyzine (3,5,6-trimethylampyzine; developmental code name W-3976B).[1][4] This drug is described as an anticholinergic and antisecretory agent.[1][4]

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]

References

  1. ↑ 1.0 1.1 1.2 1.3 Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 436. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA436. Retrieved 7 October 2024. 
  2. ↑ Milne, G.W.A. (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 547. ISBN 978-1-351-78990-5. https://books.google.com/books?id=dloPEAAAQBAJ&pg=PA547. Retrieved 7 October 2024. 
  3. ↑ Effron, D.H. (1972). Psychotropic Drugs and Related Compounds. DHEW publication. National Institute of Mental Health. p. 202. https://books.google.com/books?id=0rq7AAAAIAAJ&pg=PA202. Retrieved 7 October 2024. 
  4. ↑ 4.0 4.1 Milne, G.W.A. (2002). Drugs: Synonyms and Properties. Wiley. p. 220. ISBN 978-0-566-08491-1. https://books.google.com/books?id=QxcoEAAAQBAJ&pg=PA220. Retrieved 7 October 2024. 
  5. ↑ The Organic Chemistry of Drug Synthesis. John Wiley & Sons. 1980-05-13. ISBN 9780471043928. https://books.google.com/books?id=r-eqWrMoO18C&pg=PA298. 
  6. ↑ Miller, William (1 December 1966). "Investigational Drugs". American Journal of Health-System Pharmacy (Oxford University Press (OUP)) 23 (12): 683–687. doi:10.1093/ajhp/23.12.683. ISSN 1079-2082. 
  7. ↑ Emele Jane Frances, Wilson B Lutz, U.S. Patent 3,249,503 (1966 to Warner Lambert Pharmaceutical).



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