Ampyzine

Ampyzine

Clinical data
Other names	Dimethylaminopyrazine; W-3580B; W3580-B; W-3580-B; W3580B
ATC code	none
Identifiers
IUPAC name N,N-Dimethylpyrazin-2-amine
CAS Number	5214-29-9^Y
PubChem CID	199885
ChemSpider	21955^Y
UNII	630GTK993N
ChEMBL	ChEMBL2110770^Y
CompTox Dashboard (EPA)	DTXSID70200136
Chemical and physical data
Formula	C6H9N3
Molar mass	123.159 g·mol^−1
3D model (JSmol)	Interactive image
SMILES n1ccnc(N(C)C)c1
InChI InChI=1S/C6H9N3/c1-9(2)6-5-7-3-4-8-6/h3-5H,1-2H3^Y Key:UUINNXPPLPDRQX-UHFFFAOYSA-N^Y

Ampyzine (INNTooltip International Nonproprietary Name), also known as dimethylaminopyrazine or as ampyzine sulfate (USANTooltip United States Adopted Name) 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. 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.
2. Milne G (2018). Drugs: Synonyms and Properties. Routledge Revivals. Taylor & Francis. p. 547. ISBN 978-1-351-78990-5. Retrieved 7 October 2024.
3. Effron D (1972). Psychotropic Drugs and Related Compounds. DHEW publication. National Institute of Mental Health. p. 202. Retrieved 7 October 2024.
4. Milne G (2002). Drugs: Synonyms and Properties. Wiley. p. 220. ISBN 978-0-566-08491-1. Retrieved 7 October 2024.
5. Lednicer D, Mitscher LA (1980-05-13). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. ISBN 9780471043928.
6. 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.
7. Emele Jane Frances, Wilson B Lutz, U.S. patent 3,249,503 (1966 to Warner Lambert Pharmaceutical).

External links

• Media related to Ampyzine at Wikimedia Commons