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Information on EC 1.4.3.4 - monoamine oxidase and Organism(s) Mus musculus and UniProt Accession Q64133
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1.4.3.4 monoamine oxidaseIUBMB Comments
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines . Acts on primary amines, and also on some secondary and tertiary amines. It differs from EC 1.4.3.21, primary-amine oxidase as it can oxidize secondary and tertiary amines but not methylamine. This enzyme is inhibited by acetylenic compounds such as chlorgyline, 1-deprenyl and pargyline but, unlike EC 1.4.3.21 and EC 1.4.3.22 (diamine oxidase), it is not inhibited by semicarbazide.
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Word Map
- 1.4.3.4
- dopamine
-
antidepressant
- parkinsonism
- platelet
-
dopaminergic
-
neurotransmitter
-
tricyclic
- norepinephrine
- pargyline
-
reuptake
- deprenyl
-
deamination
- clorgyline
- catecholamine
- noradrenaline
- 5-hydroxytryptamine
-
neuroprotective
-
serotonergic
- striatal
-
anxiety
-
psychiatric
- l-dopa
- fluoxetine
- catechol-o-methyltransferase
- 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
-
biogenic
- levodopa
-
mood
- reserpine
- imipramine
-
monoaminergic
- tryptamine
-
3,4-dihydroxyphenylacetic
- benzodiazepine
- mpp+
- amphetamine
-
nigrostriatal
-
homovanillic
-
5-hydroxyindoleacetic
-
noradrenergic
-
dopac
- 5-hydroxytryptophan
- 1-methyl-4-phenylpyridinium
- paroxetine
- desipramine
-
electroconvulsive
-
panic
-
mptp-induced
-
anticholinergic
-
antidepressant-like
- drug development
- analysis
- synthesis
- medicine
The taxonomic range for the selected organisms is: Mus musculus
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Synonyms
monoamine oxidase, mao-b, mao-a, monoamine oxidase a, mao a, mao b, monoamine oxidase b, monoamine oxidase-b, monoamine oxidase-a, semicarbazide-sensitive amine oxidase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
adrenaline oxidase
-
-
-
-
epinephrine oxidase
-
-
-
-
MAO
-
-
-
-
MAO B
MAO-B
monoamine oxidase
-
-
-
-
monoamine oxidase B
monoamine:O2 oxidoreductase (deaminating)
-
-
-
-
serotonin deaminase
-
-
-
-
tyraminase
-
-
-
-
tyramine oxidase
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2
reaction mechanism of C-H bond cleavage, overview
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Deamination
-
-
-
-
redox reaction
-
-
-
-
oxidation
-
-
-
-
reduction
-
-
-
-
PATHWAY SOURCE
PATHWAYS
KEGG
-
-, -, -, -, -, -, -, -, -, -, -, -
SYSTEMATIC NAME
IUBMB Comments
amine:oxygen oxidoreductase (deaminating)
A mitochondrial outer-membrane flavoprotein (FAD) that catalyses the oxidative deamination of neurotransmitters and biogenic amines [3]. Acts on primary amines, and also on some secondary and tertiary amines. It differs from EC 1.4.3.21, primary-amine oxidase as it can oxidize secondary and tertiary amines but not methylamine. This enzyme is inhibited by acetylenic compounds such as chlorgyline, 1-deprenyl and pargyline but, unlike EC 1.4.3.21 and EC 1.4.3.22 (diamine oxidase), it is not inhibited by semicarbazide.
CAS REGISTRY NUMBER
COMMENTARY
9001-66-5
-
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
-
-
-
?
1-methyl-3-phenyl-3-pyrroline + H2O + O2
1-methyl-3-phenylpyrrole + NH3 + H2O2
oxidation is a 2-electron process. Rapid clearance of 1-methyl-3-phenylpyrrole from the brain may contribute to their lack of neurotoxicity
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + 2 H2O + 2 O2
1-methyl-4-phenylpyridinium + 3 H2O2
the parkinsonian inducing agent 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine is oxidized to 1-methyl-4-phenylpyridinium MPP+, a 4-electron oxidation product and a potent mitochondrial toxin
-
-
?
benzylamine + H2O + O2
benzaldehyde + NH3 + H2O2
monoamine oxidase B
-
-
?
kynuramine + H2O + O2
3-(2-aminophenyl)-3-oxopropanal + NH3 + H2O2
-
-
-
?
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
-
1-methyl-4-phenylpyridinium is the ultimate product
-
-
?
5-methoxy-N,N-dimethyltryptamine + H2O + O2
?
-
i.e. 5-MeO-DMT, a psychoactive indolealkylamine drug found in a variety of plant preparations, e.g. Virola snuffs and Ayahuasca, and venom of psychoactive toads, e.g. Colorado River Bufo alvarius. 5-MeO-DMT is known as a nonselective 5-HT receptor agonist. MAO-A eliminates the drug 5-MeO-DMT through oxidative deamination
-
-
?
5-methoxy-N,N-dimethyltryptamine + H2O + O2
?
-
i.e. 5-MeO-DMT, a psychoactive indolealkylamine drug found in a variety of plant preparations, e.g. Virola snuffs and Ayahuasca, and venom of psychoactive toads, e.g. Colorado River Bufo alvarius
-
-
?
additional information
?
-
MAO A KO mice display attenuated endocrine responses to major stressors, such as restraint, cold temperature, prolonged water deprivation and chronic variable stress
-
-
?
additional information
?
-
MAO A deficiency in Tg8 mice is accompanied by increased expression of different kinds of aggression, as well as by disruption of normal pattern of social interaction
-
-
?
additional information
?
-
-
MAO A deficiency in Tg8 mice is accompanied by increased expression of different kinds of aggression, as well as by disruption of normal pattern of social interaction
-
-
?
additional information
?
-
-
substrate activation of MAO can interact with adipocyte metabolism by mimicking diverse effects of insulin in addition to preventing tumor necrosis factor alpha-dependent responses
-
-
?
additional information
?
-
-
in the catalytic cycle of MAO-B, one mol each of an iminiumyl intermediate that is hydrolyzed to the aldehyde product and H2O2 are produced for each mol of monoamine substrate oxidized. These catabolic products may be neurotoxic if not rapidly inactivated by centrally located aldehyde dehydrogenase and glutathione peroxidase, respectively
-
-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine + H2O + O2
?
-
1-methyl-4-phenylpyridinium is the ultimate product
-
-
?
5-methoxy-N,N-dimethyltryptamine + H2O + O2
?
-
i.e. 5-MeO-DMT, a psychoactive indolealkylamine drug found in a variety of plant preparations, e.g. Virola snuffs and Ayahuasca, and venom of psychoactive toads, e.g. Colorado River Bufo alvarius. 5-MeO-DMT is known as a nonselective 5-HT receptor agonist. MAO-A eliminates the drug 5-MeO-DMT through oxidative deamination
-
-
?
additional information
?
-
MAO A KO mice display attenuated endocrine responses to major stressors, such as restraint, cold temperature, prolonged water deprivation and chronic variable stress
-
-
?
additional information
?
-
-
substrate activation of MAO can interact with adipocyte metabolism by mimicking diverse effects of insulin in addition to preventing tumor necrosis factor alpha-dependent responses
-
-
?
additional information
?
-
-
in the catalytic cycle of MAO-B, one mol each of an iminiumyl intermediate that is hydrolyzed to the aldehyde product and H2O2 are produced for each mol of monoamine substrate oxidized. These catabolic products may be neurotoxic if not rapidly inactivated by centrally located aldehyde dehydrogenase and glutathione peroxidase, respectively
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
i.e. guineensine, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
i.e. methylpiperate, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
i.e. guineensine, isolated from dried fruits of Piper longum, competitive inhibition
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
i.e. methylpiperate, isolated from dried fruits of Piper longum, competitive inhibition
(E)-8-(3-chlorostyryl)caffeine
-
reversible MAO-B inhibitor, a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
(E)-8-styrylcaffeine
-
reversible MAO-B inhibitor, a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
5-fluoro-alpha-methyltryptamine
-
a drug causing head-twitch response, IC50: 0.00018 mM
6-fluoro-alpha-methyltryptamine
-
a drug causing head-twitch response, IC50: 0.00018 mM
Caffeine
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
KF-17837
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
KW-6002
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
[(E)-1,3-dipropyl-7-methyl-8-(2-(3-thienyl)ethenyl)]xanthine
-
a dual-target-directed drug inhibiting MAO-B and antagonizing A2A receptors
additional information
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
additional information
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
additional information
-
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
additional information
-
inhibitors of MAO-B can be adjunctive drugs to levodopa. Neuroprotective and anti-Parkinsonian effects of A2A receptor antogonistic drugs, overview
-
additional information
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
additional information
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
additional information
-
inhibitory potencies of methylpiperate derivatives from Piper longum, no inhibition by isolated piperlonguminine
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.021
1-methyl-3-(4-chlorophenyl)-3-pyrroline
pH 7.4, 37°C, enzyme from brain
0.0635
1-methyl-3-(4-chlorophenyl)-3-pyrroline
pH 7.4, 37°C, enzyme from liver
0.0521
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
pH 7.4, 37°C, enzyme from brain
0.797
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine
pH 7.4, 37°C, enzyme from liver
additional information
additional information
kinetics with substrate kynuramine
-
additional information
additional information
kinetics with substrate kynuramine
-
additional information
additional information
-
kinetics with substrate kynuramine
-
additional information
additional information
kinetics with substrate kynuramine
-
additional information
additional information
kinetics with substrate kynuramine
-
additional information
additional information
-
kinetics with substrate kynuramine
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0235
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
inhibition of MAO-A
0.0013
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
inhibition of MAO-B
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.139
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
Mus musculus
inhibition of MAO-A
0.0271
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
Mus musculus
inhibition of MAO-A
0.0016 - 0.139
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
0.00018
5-fluoro-alpha-methyltryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
5-fluorotryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluoro-alpha-methyltryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.00018
6-fluorotryptamine
Mus musculus
-
a drug causing head-twitch response, IC50: 0.00018 mM
0.0016
(2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
Mus musculus
inhibition of MAO-B
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Tg8 is a transgenic mouse strain lacking a functional MAO A gene
SwissProt
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
monoamine oxidase A promoter is regulated by the circadian-clock components BMAL1, NPAS2, and PER2. A mutation in the clock gene Per2 in mice leads to reduced expression and activity of MAOA in the mesolimbic dopaminergic system
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
both MAO A and MAO B are membrane-associated enzymes that are located specifically to the outer mitochondrial membrane
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
the first step of the bioactivation of the Parkinsonian-inducing pro-neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, MPTP, is catalyzed by MAO-B, resulting in the ultimate product, 1-methyl-4-phenylpyridinium, a mitochondrial toxin that causes selective degeneration of nigrostriatal dopaminergic neurons in humans and experimental animals
physiological function
physiological function
-
MAO A and MAO B play roles in the oxidative catabolism of important amine neurotransmitters including serotonin, dopamine, and epinephrine. Inhibition of MAO B results in a protective effect from this cell-destructive bio-activation. MAO A functions specifically in the oxidative metabolism of serotonin although it also oxidizes dopamine effectively
physiological function
-
MAO-A eliminates the drug 5-MeO-DMT through oxidative deamination
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). AOFA_MOUSE
526
0
59602
Swiss-Prot
other Location (Reliability: 2)
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
construction of transgenic mice lacking monoamine oxidase A. The mice exhibit about 3fold higher rates of central sleep apnea than wild-types, linked to enhanced 5-hydroxytryptamine levels. Acute ondansetron and fluoxetine, and 13-day chronic fluoxetine decreas by 80% the total apnea index in the mutant mice during non-rapid eye movement sleep, with no statistically significant effect on apnea in C3H mice. Our study shows that both drugs reduce the frequency of apneic episodes attributable to increased monoamine levels in this model of MAOA deficiency, phenotypes, detailed overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
MAOA deficiency is associated with increased sleep apnea in mice and suggest that an acute or chronic excess of serotonin contributes to this phenotype
medicine
medicine
-
the enzyme is a possible target for therapeutic aproaches for obesity and insulin-resistant states
medicine
MPTP-induced apoptosis of neural progenitor cells in the subventricular zone and rostral migratory stream is, at least in part, involved in the mechanism of MAO-B-mediated conversion of MPTP into 1-methyl-4-phenylpyridinium in vivo
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Nakagawasai, O.; Arai, Y.; Satoh, S.e.; Satoh, N.; Neda, M.; Hozumi, M.; Oka, R.; Hiraga, H.; Tadano, T.
Monoamine oxidase and head-twitch response in mice. Mechanisms of alpha-methylated substrate derivatives
Neurotoxicology
25
223-232
2004
Mus musculus
Hubalek, F.; Binda, C.; Khalil, A.; Li, M.; Mattevi, A.; Castagnoli, N.; Edmondson, D.E.
Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors
J. Biol. Chem.
280
15761-15766
2005
Equus caballus, Ovis aries, Rattus norvegicus (P19643), Homo sapiens (P21397), Homo sapiens (P27338), Homo sapiens, Bos taurus (P56560), Bos taurus, Mus musculus (Q8BW75), Mus musculus
Carpene, C.; Daviaud, D.; Boucher, J.; Bour, S.; Visentin, V.; Gres, S.; Duffaut, C.; Fontana, E.; Testar, X.; Saulnier-Blache, J.S.; Valet, P.
Short- and long-term insulin-like effects of monoamine oxidases and semicarbazide-sensitive amine oxidase substrates in cultured adipocytes
Metab. Clin. Exp.
55
1397-1405
2006
Mus musculus
Bortolato, M.; Chen, K.; Shih, J.C.
Monoamine oxidase inactivation: From pathophysiology to therapeutics
Adv. Drug Deliv. Rev.
60
1527-1533
2008
Homo sapiens (P21397), Homo sapiens (P27338), Mus musculus (Q64133)
Vishnivetskaya, G.B.; Skrinskaya, J.A.; Seif, I.; Popova, N.K.
Effect of MAO A deficiency on different kinds of aggression and social investigation in mice
Aggress. Behav.
33
1-6
2007
Mus musculus (Q64133), Mus musculus
Hampp, G.; Ripperger, J.A.; Houben, T.; Schmutz, I.; Blex, C.; Perreau-Lenz, S.; Brunk, I.; Spanagel, R.; Ahnert-Hilger, G.; Meijer, J.H.; Albrecht, U.
Regulation of monoamine oxidase A by circadian-clock components implies clock influence on mood
Curr. Biol.
18
678-683
2008
Mus musculus (Q64133), Mus musculus
Ogunrombi, M.O.; Malan, S.F.; TerreBlanche, G.; Castagnoli, K.; Castagnoli, N.; Bergh, J.J.; Petzer, J.P.
Neurotoxicity studies with the monoamine oxidase B substrate 1-methyl-3-phenyl-3-pyrroline
Life Sci.
81
458-467
2007
Papio sp., Bos taurus (P56560), Mus musculus (Q8BW75), Mus musculus
He, X.J.; Uetsuka, K.; Nakayama, H.
Neural progenitor cells are protected against MPTP by MAO-B inhibitors
Neurotoxicology
29
1141-1146
2008
Mus musculus (Q8BW75)
Real, C.; Popa, D.; Seif, I.; Callebert, J.; Launay, J.M.; Adrien, J.; Escourrou, P.
Sleep apneas are increased in mice lacking monoamine oxidase A
Sleep
30
1295-1302
2007
Mus musculus (Q64133)
Lee, S.A.; Hwang, J.S.; Han, X.H.; Lee, C.; Lee, M.H.; Choe, S.G.; Hong, S.S.; Lee, D.; Lee, M.K.; Hwang, B.Y.
Methylpiperate derivatives from Piper longum and their inhibition of monoamine oxidase
Arch. Pharm. Res.
31
679-683
2008
Mus musculus (Q64133), Mus musculus (Q8BW75), Mus musculus
Petzer, J.P.; Castagnoli, N.; Schwarzschild, M.A.; Chen, J.F.; Van der Schyf, C.J.
Dual-target-directed drugs that block monoamine oxidase B and adenosine A(2A) receptors for Parkinsons disease
Neurotherapeutics
6
141-151
2009
Mus musculus, Homo sapiens (P27338)
Real, C.; Seif, I.; Adrien, J.; Escourrou, P.
Ondansetron and fluoxetine reduce sleep apnea in mice lacking monoamine oxidase A
Respir. Physiol. Neurobiol.
168
230-238
2009
Mus musculus
Shen, H.W.; Wu, C.; Jiang, X.L.; Yu, A.M.
Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics
Biochem. Pharmacol.
80
122-128
2010
Homo sapiens, Mus musculus
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