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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:38 UTC
HMDB IDHMDB0014943
Secondary Accession Numbers
  • HMDB14943
Metabolite Identification
Common NameMinaprine
DescriptionMinaprine, also known as minaprinum or cantor, belongs to the class of organic compounds known as phenylpyridazines. These are organic compounds containing a pyridazine ring substituted by a phenyl group. A study found that it acts as a reversible inhibitor of MAO-A (RIMA) in rats. Minaprine is a drug. Minaprine is a very strong basic compound (based on its pKa). Minaprine is a potentially toxic compound. In a study it has also been found to weakly inhibit acetylcholinesterase in rat brain (striatum) homogenates. 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a monoamine oxidase inhibitor antidepressant drug that was used in France for the treatment of depression until it was withdrawn from the market in 1996 because it caused convulsions.
Structure
Data?1582753238
Synonyms
ValueSource
4-(2-((4-Methyl-6-phenyl-3-pyridazinyl)amino)ethyl)morpholineChEBI
4-Methyl-3-(2-morpholinoethylamino)-6-phenylpyridazinChEBI
MinaprinaChEBI
MinaprinumChEBI
N-(4-Methyl-6-phenyl-3-pyridazinyl)-4-morpholineethanamineChEBI
CantorKegg
3-(Morpholinoethyl)amino-4-methyl-6-phenylpyridazineHMDB
Minaprine dihydrochlorideHMDB
3-(2-Morpholino-ethylamino)-4-methyl-6-phenyl pyridazine, dihydrochlorideHMDB
MINAPRINE hydrochlorideHMDB
Chemical FormulaC17H22N4O
Average Molecular Weight298.3828
Monoisotopic Molecular Weight298.179361346
IUPAC Name4-methyl-N-[2-(morpholin-4-yl)ethyl]-6-phenylpyridazin-3-amine
Traditional Nameminaprine
CAS Registry Number25905-77-5
SMILES
CC1=CC(=NN=C1NCCN1CCOCC1)C1=CC=CC=C1
InChI Identifier
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)
InChI KeyLDMWSLGGVTVJPG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyridazines. These are organic compounds containing a pyridazine ring substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyridazines and derivatives
Direct ParentPhenylpyridazines
Alternative Parents
Substituents
  • Phenylpyridazine
  • Monocyclic benzene moiety
  • Morpholine
  • Oxazinane
  • Benzenoid
  • Imidolactam
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point122 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.07 g/LNot Available
LogP2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP2.15ALOGPS
logP2.19ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)19.25ChemAxon
pKa (Strongest Basic)6.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area50.28 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.17 m³·mol⁻¹ChemAxon
Polarizability33.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uds-7950000000-d5d6a90ec878b84d86562017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uds-7950000000-d5d6a90ec878b84d86562021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0390000000-9738c44f8e588388c4522016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0950000000-d3356e07a972e95a28be2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-9700000000-020e74ff7f531306c94d2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1390000000-b7b5ed826ec7c0c9a3ff2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-2930000000-a1817395beedfdf562a72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-8920000000-d33c0ded2360f772d1e32016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00805 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00805 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00805
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4054
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMinaprine
METLIN IDNot Available
PubChem Compound4199
PDB IDNot Available
ChEBI ID51038
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. Kan JP, Mouget-Goniot C, Worms P, Biziere K: Effect of the antidepressant minaprine on both forms of monoamine oxidase in the rat. Biochem Pharmacol. 1986 Mar 15;35(6):973-8. [PubMed:3954800 ]
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Duarte CD, Barreiro EJ, Fraga CA: Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19. [PubMed:18045214 ]
  2. Contreras JM, Rival YM, Chayer S, Bourguignon JJ, Wermuth CG: Aminopyridazines as acetylcholinesterase inhibitors. J Med Chem. 1999 Feb 25;42(4):730-41. [PubMed:10052979 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2B
Uniprot ID:
P41595
Molecular weight:
54297.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [PubMed:1361012 ]
  4. Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [PubMed:2975224 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [PubMed:1361012 ]
  2. Nabeshima T, Kawashima K, Kameyama T: Effect of minaprine on cycloheximide-induced amnesia in mice. Eur J Pharmacol. 1989 Oct 10;169(2-3):249-57. [PubMed:2530096 ]
  3. Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [PubMed:2975224 ]
  4. Biziere K, Worms P, Kan JP, Mandel P, Garattini S, Roncucci R: Minaprine, a new drug with antidepressant properties. Drugs Exp Clin Res. 1985;11(12):831-40. [PubMed:3836113 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:
HTR2C
Uniprot ID:
P28335
Molecular weight:
51820.7
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kodama K, Shibata S, Ueki S: Protective effect of minaprine against the abnormal changes of 2-deoxyglucose uptake by rat hippocampal slices induced by hypoxia/hypoglycemia. Jpn J Pharmacol. 1992 Sep;60(1):33-8. [PubMed:1361012 ]
  4. Muramatsu M, Tamaki-Ohashi J, Usuki C, Araki H, Chaki S, Aihara H: 5-HT2 antagonists and minaprine block the 5-HT-induced inhibition of dopamine release from rat brain striatal slices. Eur J Pharmacol. 1988 Aug 9;153(1):89-95. [PubMed:2975224 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Duarte CD, Barreiro EJ, Fraga CA: Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19. [PubMed:18045214 ]
  2. Worms P, Kan JP, Steinberg R, Terranova JP, Perio A, Biziere K: Cholinomimetic activities of minaprine. Naunyn Schmiedebergs Arch Pharmacol. 1989 Oct;340(4):411-8. [PubMed:2586634 ]

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]