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Information on EC 2.1.1.8 - histamine N-methyltransferase
for references in articles please use BRENDA:EC2.1.1.8
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EC Tree 2 Transferases
2.1 Transferring one-carbon groups
2.1.1 Methyltransferases
2.1.1.8 histamine N-methyltransferase
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
- 2.1.1.8
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diamine
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histaminergic
- metoprine
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thr105ile
- l-histidine
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radioenzymatic
- thioperamide
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tele-methylhistamine
- aminoguanidine
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histamine-induced
- amodiaquine
- s-adenosyl-l-homocysteine
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3hhistamine
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histamine-related
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histamine-degrading
- n-myristoyltransferase
- pentagastrin
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gene-dose
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mepyramine
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pyrilamine
- phenylethanolamine
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r-alpha-methylhistamine
- histaminase
- medicine
- dimaprit
- degradation
- analysis
Reaction Schemes
showSynonyms
hnmt, histamine n-methyltransferase, histamine-n-methyltransferase, histamine methyltransferase, ntau-methyltransferase, histamine-methylating enzyme, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
histamine 1-methyltransferase
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-
-
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histamine methyltransferase
histamine N-methyltransferase
histamine-methylating enzyme
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-
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HMT
HNMT
imidazole methyltransferase
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imidazole N-methyltransferase
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imidazolemethyltransferase
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methyltransferase, histamine
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-
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S-adenosylmethionine-histamine N-methyltransferase
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histamine methyltransferase
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine
2 half-reactions in a ping pong mechanism with the intermediate formation of a methylated enzyme
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S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine
ordered sequential bi bi reaction mechanism with S-adenosylmethionine as the first substrate and histamine as the second substrate, 1-methylhistamine is the first product to leave and S-adenosylhomocysteine the second
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S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine
sequential reaction mechanism
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S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine
ordered steady state mechanism with S-adenosylmethionine being the first substrate to bind to the enzyme and N-methylhistamine being the first product to dissociate
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S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
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N-methylation
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:histamine N-tele-methyltransferase
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CAS REGISTRY NUMBER
COMMENTARY
9029-80-5
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
S-adenosyl-L-methionine + (+/-)beta-methylhistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + BI 187004
S-adenosyl-L-homocysteine + 1-(1-methyl-1H-benzimidazole-6-carbonyl)-1,2,3,4,5,5a,10,10a-octahydroindeno[2,1-b]azepine-7-carbonitrile
Substrates: BI 187004, i.e. an 11beta-hydroxysteroid dehydrogenase 1 inhibitor
Products: -
Products: -
?
S-adenosyl-L-methionine + homohistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (R)-alpha-methylhistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (R)-alpha-methylhistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (S)-alpha-methylhistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + (S)-alpha-methylhistamine
S-adenosyl-L-homocysteine + ?
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + N-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + N-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: highly specific for histamine
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: highly specific for histamine
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
-
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
-
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
-
Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: -
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: highly specific for histamine
Products: -
Products: -
?
S-adenosyl-L-methionine + histamine
S-adenosyl-L-homocysteine + Ntau-methylhistamine
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Substrates: given a negative correlation between diamine oxidase and HMT activities, the fraction of catabolized histamine decreases with increasing HMT activity
Products: -
Products: -
?
additional information
?
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
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Substrates: possible role in modulation of histamine mediated reactions in skin
Products: -
Products: -
?
additional information
?
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Substrates: major enzyme for histamine inactivation in mammalian tissues
Products: -
Products: -
?
additional information
?
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
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Substrates: major enzyme for histamine inactivation in mammalian tissues
Products: -
Products: -
?
additional information
?
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
-
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
-
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Substrates: possible role in modulation of histamine mediated reactions in skin
Products: -
Products: -
?
additional information
?
-
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Substrates: major enzyme for histamine inactivation in mammalian tissues
Products: -
Products: -
?
additional information
?
-
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
-
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
additional information
?
-
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Substrates: major enzyme for histamine inactivation in mammalian tissues
Products: -
Products: -
?
additional information
?
-
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Substrates: major pathway of histamine metabolism in mammals
Products: -
Products: -
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(5'-amino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-[4-(3-piperidin-1-yl-propoxy)-phenyl]-methanone
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50% inhibition at 0.0020 mM, simultaneously a highly potent H3 receptor ligand
(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-[4-(3-piperidin-1-yl-propoxy)-phenyl]-methanone
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50% inhibition at 0.0015 mM, simultaneously a highly potent H3 receptor ligand
(5-nitro-pyridin-2-yl)-[4-(3-piperidin-1-yl-propoxy)-benzyl]-amine
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50% inhibition at 0.0042 mM, simultaneously a highly potent H3 receptor ligand
(5-nitro-pyridin-2-yl)-{2-[4-(3-piperidin-1-yl-propoxy)-phenyl]-ethyl}-amine
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50% inhibition at 0.0028 mM, simultaneously a highly potent H3 receptor ligand
(5-nitro-pyridin-2-yl)-{3-[4-(3-piperidin-1-yl-propoxy)-phenyl]-propyl}-amine
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50% inhibition at 0.0017 mM, simultaneously a highly potent H3 receptor ligand
(5-nitro-pyridin-2-yl)-{4-[4-(3-piperidin-1-yl-propoxy)-phenyl]-butyl}-amine
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50% inhibition at 0.0017 mM, simultaneously a highly potent H3 receptor ligand
(R)-chloroquine
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50% inhibition at 0.018 mM, liver enzyme, 50% inhibition at 0.0022 mM, brain enzyme
(S)-chloroquine
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50% inhibition at 0.005 mM, liver enzyme, 50% inhibition at 0.007 mM, brain enzyme
1-(3-(4-(3,4-dihydro-2H-pyrrol-5-yl)phenoxy)propyl)piperidine
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50% inhibition at 0.0090 mM, simultaneously a highly potent H3 receptor ligand
2-(3-piperidin-1-ylpropoxy)-1,3-benzothiazole quinoline
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50% inhibition at 0.021 mM, simultaneously a highly potent H3 receptor ligand
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5-nitro-2-(3-piperidin-1-ylpropoxy)pyridine
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50% inhibition at 0.034 mM, simultaneously a highly potent H3 receptor ligand
5-nitro-N-(4-(3-piperidin-1-ylpropoxy)phenyl)pyridin-2-amine
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50% inhibition at 0.0038 mM, simultaneously a highly potent H3 receptor ligand
6-(3-piperidin-1-ylpropoxy)pyridin-3-amine
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50% inhibition at 0.053 mM, simultaneously a potent H3 receptor ligand
6-piperidin-1-yl-1-[4-(3-piperidin-1-yl-propoxy)-phenyl]-hexan-1-one
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50% inhibition at 0.0089 mM, simultaneously a highly potent H3 receptor ligand
7-chloro-4-(3-piperidin-1-ylpropoxy)quinoline
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50% inhibition at 0.0026 mM, simultaneously a potent H3 receptor ligand
8-(3-(1H-imidazol-4-yl)propoxy)-5-nitroquinoline
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50% inhibition at 0.0117 mM, simultaneously a highly potent H3 receptor ligand
diphenhydramine
potent HNMT inhibitor, occupies the histamine-binding site, thus blocks access to the enzymes active site
N-(2-(1H-imidazol-4-yl)ethyl)-1,2,3,4-tetrahydroacridin-9-amine
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50% inhibition at 0.000086 mM, simultaneously a highly potent H3 receptor ligand
N-(2-(1H-imidazol-4-yl)ethyl)-N-methylquinolin-4-amine
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50% inhibition at 0.000079 mM, simultaneously a highly potent H3 receptor ligand
N-(2-(1H-imidazol-4-yl)ethyl)quinolin-4-amine
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50% inhibition at 0.000055 mM, simultaneously a highly potent H3 receptor ligand
N-(3-(1H-imidazol-4-yl)propyl)-1,2,3,4-tetrahydroacridin-9-amine
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50% inhibition at 0.000035 mM, simultaneously a highly potent H3 receptor ligand
N-(3-(1H-imidazol-4-yl)propyl)-2-methylquinolin-4-amine
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50% inhibition at 0.000054 mM, simultaneously a highly potent H3 receptor ligand
N-(3-(1H-imidazol-4-yl)propyl)-N-methylquinolin-4-amine
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50% inhibition at 0.000035 mM, simultaneously a highly potent H3 receptor ligand
N-(3-(1H-imidazol-4-yl)propyl)quinolin-4-amine
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50% inhibition at 0.000024 mM, simultaneously a highly potent H3 receptor ligand
N-[2(benzhydryloxy)ethyl] N N-dimethylamine
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diphenhydramine, competitive inhibitor
N2-[2-[4-(3-piperidin-1-yl-propoxy)-phenyl]-ethyl]-pyridine-2,5-diamine
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50% inhibition at 0.00031 mM, simultaneously a highly potent H3 receptor ligand
N2-[3-[4-(3-piperidin-1-yl-propoxy)-phenyl]-propyl]-pyridine-2,5-diamine
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50% inhibition at 0.0013 mM, simultaneously a highly potent H3 receptor ligand
N2-[4-[4-(3-piperidin-1-yl-propoxy)-phenyl]-butyl]-pyridine-2,5-diamine
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50% inhibition at 0.00034 mM, simultaneously a highly potent H3 receptor ligand
[4-(3-piperidin-1-yl-propoxy)-phenyl]-(1-quinolin-4-yl-piperidin-4-yl)-methanone
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50% inhibition at 0.00031 mM, simultaneously a highly potent H3 receptor ligand
amodiaquine
potent HNMT inhibitor, occupies the histamine-binding site, thus blocks access to the enzymes active site
Metoprine
potent HNMT inhibitor, occupies the histamine-binding site, thus blocks access to the enzymes active site
tacrine
-
50% inhibition at 0.00046 mM for enzyme of embryonic kidney, at 0.0007 mM for recombinant brain enzyme
tacrine
potent HNMT inhibitor, occupies the histamine-binding site, thus blocks access to the enzymes active site
additional information
-
overview: adenosine analogs bearing a lipophilic side chain
-
additional information
near the N-terminus of HNMT, several aromatic residues (Phe9, Tyr15, and Phe19) adopt different rotamer conformations or become disordered in the enzyme-inhibitor complexes, accommodating the diverse, rigid hydrophobic groups of the inhibitors, maximized shape complementarity between the protein aromatic side-chains and aromatic rings of the inhibitors are responsible for the tight binding of the different inhibitors
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
enzyme activities are increased in tissues of amitriptyline treated guinea pigs
additional information
-
enzyme activities are increased in spleen and kidney of amitriptyline treated rats
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2 - 7.4
7.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 10.5
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about 50% of maximum activity at pH 6.5 and pH 10.5, N-methylhistamine
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
37