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a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.^[2][3]

Minaprine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N06AX07 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1] In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	2-2.5 hours
Identifiers
IUPAC name 4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine
CAS Number	25905-77-5 Y
PubChem CID	4199
ChemSpider	4054 Y
UNII	00U7GX0NLM
KEGG	D05039 Y
ChEMBL	ChEMBL278819 Y
CompTox Dashboard (EPA)	DTXSID5048477
ECHA InfoCard	100.043.012
Chemical and physical data
Formula	C17H22N4O
Molar mass	298.390 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=NN=C1NCCN2CCOCC2)C3=CC=CC=C3
InChI 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

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]

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]