Molindone
Basic information
- CAS
7416-34-4- Standard SMILES
CCc1c(C)[nH]c2c1C(=O)C(CN1CCOCC1)CC2- InChIKey
KLPWJLBORRMFGK-UHFFFAOYSA-N- Molecular formula
- C16H24N2O2
- Average molar mass
- 276.37 g/mol
- Monoisotopic mass
- 276.18377801
Overview
Molindone is a member of indoles.
Names & identifiers
- Preferred name
- Molindone
- IUPAC
- 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one
- English name
- 3-Ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-one
- Molecular formula
- C16H24N2O2
- Molecular weight
- 276.37
Names & synonyms
MOLINDONE7416-34-4(+-)-MolindoneMolindona3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-1,5,6,7-tetrahydroindol-4-oneMolindonumRT3Y3QMF8N3-Ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)indol-4(5H)-one3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-oneIndol-4(5H)-one, 3-ethyl-6,7-dihydro-2-methyl-5-(morpholinomethyl)-3-Ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-4H-indol-4-oneDTXSID9023332
Show more names
C07230EN-1733AEOS-60951Molintoneindol-4(5h)-oneMOLINDONE USP/EP/BP3-Ethyl-2-Methyl-5-(Morpholin-4-ylMethyl)-1,5,6,7-
4H-Indol-4-one, 3-ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-RefChem:56582DTXCID603332N05AE02819-661-9Molindonum [INN-Latin]Molindona [INN-Spanish](+/-)-Molindone
Database identifiers
- CAS
7416-34-4- PubChem CID
- 23897
- DTXSID
DTXSID9023332- ChEMBL
CHEMBL460- ChEBI
CHEBI:6965- UNII
- RT3Y3QMF8N
- EC Number
- 819-661-9
- Nikkaji
- J8.932J
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 45.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 354
Experimental & physicochemical properties
LogP1.54
Color/FormCRYSTALS
Solubility
WHITE CRYSTALLINE POWDER; FREELY SOL IN WATER & ALCOHOL /HYDROCHLORIDE/
4.74e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antipsychotic Agents
Melting Point
180-181 °C
180.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 180 · 180-181°
- Boiling point
- 462.9 · 462.9±45.0 °C(Predicted)
- Density
- 1.14 · 1.140±0.06 g/cm3(Predicted)
- solubility
- 2 O: · H2O: 19 mg/mL
- form
- solid
- pka
- 6.9 · pKa 6.9(H2O,t =25,I=0.2) (Uncertain)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Special ReportsOwen RR Jr, Cole JO; J Clin Psychopharmacol 9 (4): 268-76 (1989). Molindone hydrochloride: A review of laboratory and clinical findings
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Hepatotoxicity
Liver test abnormalities have been reported to occur in a small proportion of patients on long term therapy with molindone, but elevations are uncommonly above 3 times the upper limit of normal. The aminotransferase abnormalities are usually mild, asymptomatic and transient, reversing even with continuation of medication. Instances of clinically apparent acute liver injury have been reported due to molindone, but are rare. The onset of injury is within 4 to 8 weeks, and the pattern of serum enzyme elevations is typically hepatocellular. Jaundice is uncommon and most cases are self-limited and mild. Immunoallergic features and autoantibody formation are not typical.
Human Toxicity Excerpts
TRANSIENT DROWSINESS IS MOST FREQUENT ADVERSE REACTION; PARKINSONIAN REACTIONS, RESTLESSNESS, INSOMNIA, DEPRESSION, BLURRED VISION, DRY MOUTH, NAUSEA & TACHYCARDIA OCCUR LESS FREQUENTLY. /HYDROCHLORIDE/
/IN ADDN TO PARKINSONIAN SYNDROME/, ANOTHER EXTRAPYRAMIDAL EFFECT SEEN DURING ANTIPSYCHOTIC DRUG THERAPY IS AKATHISIA. ... /IT/ REFERS TO COMPELLING NEED OF PT TO BE IN CONSTANT MOVEMENT RATHER THAN TO ANY SPECIFIC MOVEMENT PATTERN. ... /PT/ MAY BE UNABLE TO ... CONTROL /THIS EFFECT/. /ANTIPSYCHOTIC DRUGS/
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Molindone is a dihydroindolone compound which is not structurally related to the phenothiazines, the butyrophenones, or the thioxanthenes. Molindone has a pharmacological profile in laboratory animals which predominantly resembles that of major tranquilizers causing reduction of spontaneous locomotion and aggressiveness, suppression of a conditioned response and antagonism of the bizarre stereotyped behavior and hyperactivity induced by amphetamines. In addition, molindone antagonizes the depression caused by the tranquilizing agent tetrabenazine.
Mechanism of Action
The exact mechanism has not been established, however, based on electroencephalogram (EEG) studies, molindone is thought to act by occupying (antagonizing) dopamine (D2) receptor sites in the reticular limbic systems in the brain, thus decreasing dopamine activity. Decreased dopamine activity results in decreased physiological effects normally induced by excessive dopamine stimulation, such as those typically seen in manifestations of psychotic disorders.
INFORMATION IS INADEQUATE TO DETERMINE SPECIFIC ACTIONS OF MOLINDONE...
THIS ANTIPSYCHOTIC AGENT IS A DIHYDROINDOLONE DERIV. IT IS NOT CHEM RELATED TO PHENOTHIAZINES, BUTYROPHENONES OR THIOXANTHENES, BUT PHARMACOLOGIC ACTIONS ARE SIMILAR TO THOSE OF PIPERAZINE PHENOTHIAZINES.
Metabolism/MetabolitesMost likely hepatic. 36 metabolites have been recognized, some of which may be active.
FDA Pharmacological Classification
RT3Y3QMF8N
MOLINDONE
Established Pharmacologic Class [EPC] - Typical Antipsychotic
Molindone is a Typical Antipsychotic.
MeSH Pharmacological Classification
Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
4 records
Compound notes
Loading…