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Minaprine

Chemical compound From Wikipedia, the free encyclopedia

Minaprine

Minaprine (INN, USAN, BAN; brand names Brantur, Cantor) is a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.[2][3]

Quick Facts Clinical data, AHFS/Drugs.com ...
Minaprine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life2-2.5 hours
Identifiers
  • 4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.012
Chemical and physical data
FormulaC17H22N4O
Molar mass298.390 g·mol−1
3D model (JSmol)
  • CC1=CC(=NN=C1NCCN2CCOCC2)C3=CC=CC=C3
  • InChI=1S/C17H22N4O/c1-14-13-16(15-5-3-2-4-6-15)19-20-17(14)18-7-8-21-9-11-22-12-10-21/h2-6,13H,7-12H2,1H3,(H,18,20) Y
  • Key:LDMWSLGGVTVJPG-UHFFFAOYSA-N Y
Close

A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats.[4] It has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates.[5]

It has demonstrated significant antibiotic activity against M. chelonae and M. abscessus in tests with antibiotic resistant bacteria.[6]

Synthesis

The first synthesis of minaprine was disclosed in patents published in 1979.[7]

Thumb

The final step is the reaction between a chloro-substituted pyridazine and the primary amine group of a morpholine derivative.[7][8] The required pyridazine can be made by the reaction of acetophenone and pyruvic acid, followed by ring formation using hydrazine, giving a pyrazidinone. Treatment of this with phosphoryl chloride converts it to the required chloro derivative.[2]

References

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