Molindone

Molindone

Systematic (IUPAC) name
3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)- 1,5,6,7-tetrahydro-4H-indol-4-one
Clinical data
Trade names	Moban
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682238
Pregnancy category	C
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	1.5 hours
Excretion	Minor, renal and fecal
Identifiers
CAS Number	7416-34-4 Y
ATC code	N05AE02 (WHO)
PubChem	CID: 23897
IUPHAR/BPS	207
DrugBank	DB01618 N
ChemSpider	22342 Y
UNII	RT3Y3QMF8N Y
KEGG	D08226 Y
ChEMBL	CHEMBL460 Y
Chemical data
Formula	C16H24N2O2
Molecular mass	276.374 g/mol
SMILES O=C2c1c(c(nc1CCC2CN3CCOCC3)C)CC
InChI InChI=1S/C16H24N2O2/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18/h12,17H,3-10H2,1-2H3 Y Key:KLPWJLBORRMFGK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Molindone (Moban) is a therapeutic antipsychotic, used in the treatment of schizophrenia. It works by blocking the effects of dopamine in the brain, leading to diminished psychoses. It is rapidly absorbed when taken orally.

It is sometimes described as a typical antipsychotic, and sometimes described as an atypical antipsychotic.

Molindone was discontinued by its sole supplier, Endo Pharmaceuticals, on January 13, 2010.

Adverse effects

Main article: Typical antipsychotic

The side effect profile of molindone is similar to that of other typical antipsychotics. Unlike most antipsychotics, however, molindone use is associated with weight loss.

Synthesis

Molindone synthesis: SCHOEN KARL, J PACHTER IRWIN; BE 670798  (1965 to Endo Lab).

Condensation of oximinoketone 2 (from nitrosation of 3-pentanone), with 1,3-Cyclohexanedione (1) in the presenec of zinc and acetic acid leads directly to the partly reduced indole derivative 6. The transformation may be rationalized by assuming as the first step, reduction of 2 to the corresponding α-aminoketone. Conjugate addition of the amine to 1 followed by elimination of hydroxide (as water) would give ene-aminoketone 3. This enamine may be assumed to be in tautomeric equilibrium with imine 4. Aldol condensation of the side chain carbonyl group with the doubly activated ring methylene would then result in cyclization to pyrrole 5; simple tautomeric transformation would then give the observed product. Mannich reaction of 6 with formaldehyde and morpholine gives the tranquilizer molindone (7).

See also

• Losindole
• Piquindone