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Information on EC 2.1.1.49 - amine N-methyltransferase
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EC Tree
2.1.1.49 amine N-methyltransferaseIUBMB Comments
An enzyme of very broad specificity; many primary, secondary and tertiary amines can act as acceptors, including tryptamine, aniline, nicotine and a variety of drugs and other xenobiotics.
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Word Map
- 2.1.1.49
-
n-methylation
-
smoke
- cyp2a6
- urine
- n-methyltransferases
-
flavin-containing
- monooxygenase
-
udp-glucuronosyltransferases
-
smoking
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
arylamine n-methyltransferase, amine n-methyltransferase, nicotine n-methyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
arylamine N-methyltransferase
-
-
-
-
EC 2.1.1.81
-
-
formerly
-
methyltransferase, tryptamine
-
-
-
-
nicotine N-methyltransferase
-
-
-
-
tryptamine methyltransferase
-
-
-
-
tryptamine N-methyltransferase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
S-adenosyl-L-methionine + an amine = S-adenosyl-L-homocysteine + a methylated amine
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
methyl group transfer
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
S-adenosyl-L-methionine:amine N-methyltransferase
An enzyme of very broad specificity; many primary, secondary and tertiary amines can act as acceptors, including tryptamine, aniline, nicotine and a variety of drugs and other xenobiotics.
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CAS REGISTRY NUMBER
COMMENTARY
51377-47-0
-
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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
(R)-isosalsoline + methyl group donor
N-methyl-(R)-isosalsoline + demethylated methyl group donor
-
-
N-methyl-(R)-isosalsoline is enzymatically formed in liver and can be transported into the brain from blood, it may act as neurotransmitter
?
S-adenosyl-L-methionine + 1,2,3,4-tetrahydroisoquinoline
S-adenosyl-L-homocysteine + N-methyl-1,2,3,4-tetrahydroisoquinoline
-
amine N-methyltransferase A
-
?
S-adenosyl-L-methionine + 5-methyloxytryptamine
?
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
?
-
substrate with highest apparent kcat
-
-
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
S-adenosyl-L-methionine + aniline
S-adenosyl-L-homocysteine + N-methylaniline
-
poor substrate
-
-
?
S-adenosyl-L-methionine + anisidine
?
-
higher activity with transferase B
-
-
?
S-adenosyl-L-methionine + beta-phenylethylamine
?
-
5-methyltetrahydrofolate can replace S-adenosyl-L-methionine as methyl donor
-
-
?
S-adenosyl-L-methionine + imidazole
?
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + isosalsoline
S-adenosyl-L-homocysteine + N-methylisosalsoline
-
isosalsoline is identical with 7-hydroxy-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline, stereospecific N-methylation by amine N-methyltransferase A, (+)-(R)-enantiomer is preferentially methylated
-
?
S-adenosyl-L-methionine + N-methylbutylamine
S-adenosyl-L-homocysteine + N,N-dimethylbutylamine
-
only transferase A
-
-
?
S-adenosyl-L-methionine + N-methylcyclohexylamine
S-adenosyl-L-homocysteine + N,N-dimethylcyclohexylamine
-
only transferase A
-
-
?
S-adenosyl-L-methionine + N-methyltryptamine
S-adenosyl-L-homocysteine + N,N-dimethyltryptamine
S-adenosyl-L-methionine + phenyltetrahydropyridine
?
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + pyrazole
?
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + salsolidine
S-adenosyl-L-homocysteine + N-methylsalsolidine
-
salsolidine is identical with 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline, stereospecific N-methylation by amine N-methyltransferase A, (-)-(S)-enantiomer is preferentially methylated
-
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
-
-
-
-
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
-
-
no methylation of indolic nitrogen
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
-
-
no methylation of indolic nitrogen
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
-
-
-
-
?
S-adenosyl-L-methionine + alpha-N-methyltryptamine
S-adenosyl-L-homocysteine + alpha,alpha-N,N-dimethyltryptamine
-
-
N,N-dimethyltryptamine as product
?
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
-
enzymes participate in detoxication, recycling of drugs after initial demethylation
-
-
?
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
-
xenobiotic biotransforming enzyme, enzyme is leaked easily into the blood stream due to an increased membrane permeability of hepatocytes caused by cholestasis
-
-
?
S-adenosyl-L-methionine + desmethylimipramine
S-adenosyl-L-homocysteine + imipramine
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + desmethylimipramine
S-adenosyl-L-homocysteine + imipramine
-
higher activity with transferase A
-
-
?
S-adenosyl-L-methionine + N-methyltryptamine
S-adenosyl-L-homocysteine + N,N-dimethyltryptamine
-
-
-
-
?
S-adenosyl-L-methionine + N-methyltryptamine
S-adenosyl-L-homocysteine + N,N-dimethyltryptamine
-
-
-
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
i.e. 3-[2-aminoethyl] indole, best substrate, two N-methyltransferases: A and B, non-specific
-
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
i.e. 3-[2-aminoethyl] indole, best substrate, two N-methyltransferases: A and B, non-specific
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
i.e. 3-[2-aminoethyl] indole, best substrate, two N-methyltransferases: A and B, non-specific
-
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
i.e. 3-[2-aminoethyl] indole, best substrate, two N-methyltransferases: A and B, non-specific
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
two N-methyltransferases, non-specific or specific for tryptamine, 5-methyltetrahydrofolate can replace S-adenosyl-L-methionine as methyl donor
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
S-adenosyl-L-methionine-dependent enzyme
-
?
S-adenosyl-L-methionine + tryptamine
S-adenosyl-L-homocysteine + alpha-N-methyltryptamine
-
i.e. 3-[2-aminoethyl] indole, best substrate, two N-methyltransferases: A and B, non-specific
-
?
additional information
?
-
-
two N-methyltransferases A and B with very broad but overlapping substrate specificity for primary and secondary amines, lipophilic substrates, overview poor substrates, no substrates: N-acetylserotonine, 4-aminoacetophenone, 4-aminophenol, benzamide, 4-chloroaniline, deoxyepinephrine, 1,4-diaminobutane, dopamine, 1-ethanol-2-amine, ethylenediamine, histamine, histidine methylester, 3-hydroxytryptamine, indole, pyrrole, methylamine, N-methyldopamine, nicotinamide, octopamine, phenylalanine, phenylethanolamine, theophylline, tryptophan, tyrosine, N,N-dimethyltryptamine
-
-
?
additional information
?
-
-
two N-methyltransferases A and B with very broad but overlapping substrate specificity for primary and secondary amines, lipophilic substrates, overview poor substrates, no substrates: N-acetylserotonine, 4-aminoacetophenone, 4-aminophenol, benzamide, 4-chloroaniline, deoxyepinephrine, 1,4-diaminobutane, dopamine, 1-ethanol-2-amine, ethylenediamine, histamine, histidine methylester, 3-hydroxytryptamine, indole, pyrrole, methylamine, N-methyldopamine, nicotinamide, octopamine, phenylalanine, phenylethanolamine, theophylline, tryptophan, tyrosine, N,N-dimethyltryptamine
-
-
?
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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
(R)-isosalsoline + methyl group donor
N-methyl-(R)-isosalsoline + demethylated methyl group donor
-
-
N-methyl-(R)-isosalsoline is enzymatically formed in liver and can be transported into the brain from blood, it may act as neurotransmitter
?
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
-
enzymes participate in detoxication, recycling of drugs after initial demethylation
-
-
?
S-adenosyl-L-methionine + an amine
S-adenosyl-L-homocysteine + an N-methylamine
-
xenobiotic biotransforming enzyme, enzyme is leaked easily into the blood stream due to an increased membrane permeability of hepatocytes caused by cholestasis
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
substrate inhibition, but not by tryptamine and 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
biosynthesis of enzyme is induced in response to obstructive jaundice
-
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.015
S-adenosyl-L-methionine
-
1 mM tryptamine as methyl acceptor, pH 8.5
0.01
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
-
transferase A, pH 7.6
28.3
tryptamine
-
mitochondrial enzyme, cholestatic liver, S-adenosyl-L-methionine
32.5
tryptamine
-
mitochondrial enzyme, control liver, S-adenosyl-L-methionine
34.1
tryptamine
-
microsomal enzyme, cholestatic liver, S-adenosyl-L-methionine
35.6
tryptamine
-
microsomal enzyme, control liver, S-adenosyl-L-methionine
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.667
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
-
transferase A, pH 7.6
3.67
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
-
transferase B, pH 7.6
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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
-
specific activities of serum, control and cholestatic liver in cytosolic, mitochondrial and microsomal preparations for 0.5, 1, 2, 3, 7, 14, 28 and 42 days after common bile duct ligation, activities of mitochondrial and microsomal enzyme in cholestatic liver and of serum enzyme increase after common bile duct ligation, Vmax-values
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2 - 8.9
-
tryptamine, about half-maximal activity at pH 7.2 and 8.9, transferase A
7.5 - 8.8
-
tryptamine, about half-maximal activity at pH 7.5 and 90% at pH 8.8, transferase B
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
rats with common bile duct ligation and obstructive jaundice respectively
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
investigation of enzyme in serum, after common bile duct ligation for a period of 42 days
brenda
-
investigation of enzyme in cholestatic liver, induced by common bile duct ligation for a period of 42 days
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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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). INMT_HUMAN
263
0
28891
Swiss-Prot
other Location (Reliability: 2)
INMT_MOUSE
264
0
29460
Swiss-Prot
other Location (Reliability: 1)
INMT_PONAB
263
0
28848
Swiss-Prot
other Location (Reliability: 1)
INMT_RABIT
263
0
28955
Swiss-Prot
other Location (Reliability: 1)
B7PT33_IXOSC
293
0
32115
TrEMBL
Secretory Pathway (Reliability: 4)
A0A8B6E6W7_MYTGA
262
0
29605
TrEMBL
other Location (Reliability: 1)
B7QKH3_IXOSC
294
0
32285
TrEMBL
Mitochondrion (Reliability: 4)
B7QCE1_IXOSC
150
0
17169
TrEMBL
other Location (Reliability: 3)
B7PS37_IXOSC
257
0
28687
TrEMBL
other Location (Reliability: 3)
B7FIM0_MEDTR
358
0
39691
TrEMBL
other Location (Reliability: 4)
B7Q6R1_IXOSC
113
0
13305
TrEMBL
other Location (Reliability: 2)
A0A8B6D8H7_MYTGA
222
0
24894
TrEMBL
other Location (Reliability: 5)
B7Q2U6_IXOSC
296
0
33107
TrEMBL
Mitochondrion (Reliability: 2)
B7QAZ0_IXOSC
117
0
13714
TrEMBL
other Location (Reliability: 1)
B7PRU6_IXOSC
289
0
32280
TrEMBL
other Location (Reliability: 2)
A0A2P6RB88_ROSCH
358
0
39605
TrEMBL
other Location (Reliability: 3)
A0A396J0N2_MEDTR
358
0
39770
TrEMBL
other Location (Reliability: 5)
A0A8B6D8N9_MYTGA
262
0
29570
TrEMBL
other Location (Reliability: 1)
B5DFP9_XENTR
266
0
30066
TrEMBL
other Location (Reliability: 1)
Q6P7F9_XENLA
253
0
28322
TrEMBL
other Location (Reliability: 3)
A0A072VA70_MEDTR
354
0
39306
TrEMBL
other Location (Reliability: 5)
B7PL43_IXOSC
120
0
13383
TrEMBL
other Location (Reliability: 3)
B7P1Z1_IXOSC
142
0
15456
TrEMBL
other Location (Reliability: 1)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
additional information
additional information
-
aggregation upon denaturation leads to 60 kDa and 90 kDa fractions
additional information
-
aggregation upon denaturation leads to 60 kDa and 90 kDa fractions
-
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
two N-methyltransferases A and B separable by ammonium sulfate fractionation, HPLC-ion exchange chromatography
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Crooks, P.A.; Godin, C.S.; Nwosu, C.G.; Ansher, S.S.; Jakoby, W.B.
Reevaluation of the products of tryptamine catalyzed by rabbit liver N-methyltransferases
Biochem. Pharmacol.
35
1600-1603
1986
Oryctolagus cuniculus, Oryctolagus cuniculus New Zealand
brenda
Hsu, L.L.; Mandell, A.J.
Multiple N-methyltransferases for aromatic alkylamines in brain
Life Sci.
13
847-858
1973
Rattus norvegicus
brenda
Ansher, S.S.; Jakoby, W.B.
Amine N-methyltransferases from rabbit liver
J. Biol. Chem.
261
3996-4001
1986
Oryctolagus cuniculus, Oryctolagus cuniculus New Zealand
brenda
Bahnmaier, A.H.; Woesle, B.; Thomas, H.
Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline and salsolidine by amine N-methyltransferase A from bovine liver
Chirality
11
160-165
1999
Bos taurus
brenda
Kim, Y.H.; Joo, I.
Arylamine N-methyltransferase and thiol methyltransferase activities in cholestatic rat liver induced by common bile duct ligation
Exp. Mol. Med.
33
23-28
2001
Rattus norvegicus
brenda
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