Basic information
- CAS
25905-77-5- Standard SMILES
Cc1cc(-c2ccccc2)nnc1NCCN1CCOCC1- InChIKey
LDMWSLGGVTVJPG-UHFFFAOYSA-N- Molecular formula
- C17H22N4O
- Average molar mass
- 298.4 g/mol
- Monoisotopic mass
- 298.17936134
Overview
Minaprine is a secondary amine, a member of pyridazines and a member of morpholines. It has a role as an antidepressant, a cholinergic drug, an antiparkinson drug, a serotonin uptake inhibitor and a dopamine uptake inhibitor.
Names & identifiers
- Preferred name
- Minaprine
- IUPAC
- 4-methyl-N-(2-morpholin-4-ylethyl)-6-phenylpyridazin-3-amine
- English name
- Minaprine dihydrochloride
- Molecular formula
- C17H22N4O
- Molecular weight
- 298.38
Names & synonyms
minaprine25905-77-5CantorMinaprinaMinaprinumAGR 1240N-(4-Methyl-6-phenyl-3-pyridazinyl)-4-morpholineethanamineAgr-12404-Morpholineethanamine, N-(4-methyl-6-phenyl-3-pyridazinyl)-4-Methyl-3-(2-morpholinoethylamino)-6-phenylpyridazinCB 300384-(2-((4-Methyl-6-phenyl-3-pyridazinyl)amino)ethyl)morpholine
Show more names
TS-370minaprinMinaprin diHClMinaprine 2HClMINAPRINE HYDROCHLORIDEMINAPRIN DIHYDROCHLORIDE
4-methyl-N-[2-(morpholin-4-yl)ethyl]-6-phenylpyridazin-3-amine00U7GX0NLMCB-30038DTXSID5048477CHEBI:510384-[2-[(4-Methyl-6-phenyl-3-pyridazinyl)amino]ethyl]morpholine4-methyl-N-(2-(morpholin-4-yl)ethyl)-6-phenylpyridazin-3-amine3-(morpholinoethyl)amino-4-methyl-6-phenylpyridazine
Database identifiers
- CAS
25905-77-5- PubChem CID
- 4199
- DTXSID
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 50.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 316
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP
2
2.03
Solubility7.01e-02 g/L
Melting Point122 °C
Physical DescriptionSolid
Collision Cross Section172.37 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 122 ° · 122°
- Boiling point
- 531.2 · 531.2±50.0 °C(Predicted)
- Density
- 1.156 · 1.156±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 35 mg/mL · DMSO : ≥ 35 mg/mL (117.30 mM)
- pka
- 6.8 · 6.80±0.10(Predicted)
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)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- QE3477830
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Minaprine is an amino-phenylpyridazine antidepressant reported to be relatively free of cardiotoxicity, drowsiness, and weight gain. Similar to other antidepressant treatments, minaprine attenuates the beta-adrenergic receptor function. Studies have also shown that minaprine improves memory consolidation and that repeated drug administration leads to potentiation of this effect. Moreover, the effects of minaprine on memory consolidation are related to its dopaminergic action.
Mechanism of Action
Minaprine binds to serotonin type 2 receptors and to dopamine D1 and D2 type receptors. It also binds to the serotonin reuptake pump. Therefore, minaprine blocks the reuptake of both dopamine and serotonin. It is also, to a slight degree, cholinomimetic. Thus it may exhibit both mood-brightening and nootropic properties. It also acts as a reversible inhibitor of MAO-A (RIMA).It has also been found to inhibit acetylcholinesterase.
Metabolism/Metabolites
Hepatic. Cytochrome P4502D is responsible for the 4-hydroxylation of minaprine to 4-hydroxyminaprine.
Minaprine has known human metabolites that include 4-Hydroxyminaprine.
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
Cellular LocationsCytoplasm
Applications
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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