Ampyzine
 | |
| Clinical data | |
|---|---|
| Other names | Dimethylaminopyrazine; W-3580B; W3580-B; W-3580-B; W3580B |
| ATC code |
|
| Identifiers | |
| |
| 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) | |
| |
| |
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
[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.[5][6][7]
References
[edit]- ^ a b c d Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 436. ISBN 978-1-4757-2085-3. Retrieved 7 October 2024.
- ^ Milne G (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 547. ISBN 978-1-351-78990-5. Retrieved 7 October 2024.
- ^ Effron D (1972). Psychotropic Drugs and Related Compounds. DHEW publication. National Institute of Mental Health. p. 202. Retrieved 7 October 2024.
- ^ a b Milne G (2002). Drugs: Synonyms and Properties. Wiley. p. 220. ISBN 978-0-566-08491-1. Retrieved 7 October 2024.
- ^ Lednicer D, Mitscher LA (1980-05-13). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. ISBN 9780471043928.
- ^ Miller W (1 December 1966). "Investigational Drugs". American Journal of Health-System Pharmacy. 23 (12). Oxford University Press (OUP): 683–687. doi:10.1093/ajhp/23.12.683. ISSN 1079-2082.
- ^ 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
 | This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it. |