Showing metabocard for N-Methylphenylethanolamine (MMDBc0031999)

Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-18 01:58:05 UTC
Update Date2025-11-05 17:13:01 UTC
Metabolite IDMMDBc0031999
Metabolite Identification
Common NameN-Methylphenylethanolamine
DescriptionN-Methylphenylethanolamine is a member of the class of phenylethanolamines, which are organic compounds characterized by a phenyl group attached to an ethanolamine structure. This compound is involved in various metabolic pathways, particularly in the context of enzymatic reactions mediated by monoamine oxidase (MAO). It has been identified as a metabolite in several studies, where it was found alongside other metabolites altered by specific interventions, such as GEF (PMID:36561332 ). Additionally, N-methylphenylethanolamine has been shown to be a substrate for both type A and type B MAO, indicating its role in the catabolism of amines (PMID:6775642 ). In experimental settings, it was observed that N-methylphenylethanolamine and its derivatives, when injected into mice, rapidly entered the brain and were metabolized by MAO to produce methylamine and corresponding aldehydes, highlighting its involvement in central nervous system processes (PMID:6435178 ). Furthermore, its partial generalization as a potential metabolite of phenethylamine suggests its relevance in broader metabolic networks (PMID:3737623 ). Overall, N-methylphenylethanolamine serves as an important compound in both biochemical and pharmacological contexts.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9ac9285058>


  Mrv0541 02231219062D          

 11 11  0  0  0  0            999 V2000
    0.3266    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415    0.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9ac9285058>

HMDB0001387
     RDKit          3D
N-Methylphenylethanolamine
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.0070    1.2152   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.6221    0.4610 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995   -0.7149   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -1.3081    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -2.5995    0.0524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483   -0.5102    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.5431   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.2029   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050    1.0039   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.0503    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    0.2959    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.4799   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    1.9276    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.7770   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    0.5761    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -0.7720   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603   -1.3423    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.4633    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -2.5514   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -1.1674   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025    0.1685   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    1.5886   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    1.6950    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942    0.3692    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9ac9285058>


  Mrv0541 02231219062D          

 11 11  0  0  0  0            999 V2000
    0.3266    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919    0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3300   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415    0.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1068    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954    1.2753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0415   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565    0.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8218    0.4434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7565   -0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5334    0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031999

> <DATABASE_NAME>
MIME

> <SMILES>
CNCC(O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

> <INCHI_KEY>
ZCTYHONEGJTYQV-UHFFFAOYSA-N

> <FORMULA>
C9H13NO

> <MOLECULAR_WEIGHT>
151.2056

> <EXACT_MASS>
151.099714043

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.258363129922493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(methylamino)-1-phenylethan-1-ol

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
0.9012597036666667

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.121327899503143

> <JCHEM_PKA_STRONGEST_BASIC>
9.434562222633247

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
45.268499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
halostachine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9ac9285058>

HMDB0001387
     RDKit          3D
N-Methylphenylethanolamine
 24 24  0  0  0  0  0  0  0  0999 V2000
    3.0070    1.2152   -0.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8796    0.6221    0.4610 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995   -0.7149   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3763   -1.3081    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2409   -2.5995    0.0524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8483   -0.5102    0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -0.5431   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603    0.2029   -1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1050    1.0039   -0.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5323    1.0503    0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4010    0.2959    1.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.4799   -0.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    1.9276    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.7770   -1.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1276    0.5761    1.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5534   -0.7720   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4603   -1.3423    0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4646   -1.4633    1.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3010   -2.5514   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0129   -1.1674   -1.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0025    0.1685   -2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    1.5886   -0.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9780    1.6950    1.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9942    0.3692    2.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
  9 22  1  0
 10 23  1  0
 11 24  1  0
M  END
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PDB for #<Metabolite:0x00007f9ac9285058>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       0.610   0.077   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.732   0.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.616  -1.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.944   0.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.066   0.071   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.738   2.381   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.944  -2.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.279   0.077   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -3.401   0.828   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.279  -1.463   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.729   0.058   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    4   10                                                       
CONECT    9    5   11                                                       
CONECT   10    7    8                                                       
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f9ac9285058>

COMPND    HMDB0001387
HETATM    1  C1  UNL     1       3.007   1.215  -0.262  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.880   0.622   0.461  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.600  -0.715  -0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.376  -1.308   0.599  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.241  -2.599   0.052  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.848  -0.510   0.258  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.428  -0.543  -0.979  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.560   0.203  -1.316  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.105   1.004  -0.342  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.532   1.050   0.913  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.401   0.296   1.227  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.735   0.480  -0.617  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.516   1.928   0.419  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.577   1.777  -1.144  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.128   0.576   1.488  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.553  -0.772  -1.101  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.460  -1.342   0.329  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.465  -1.463   1.689  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.301  -2.551  -0.933  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.013  -1.167  -1.732  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.002   0.168  -2.303  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.976   1.589  -0.579  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.978   1.695   1.676  1.00  0.00           H  
HETATM   24  H13 UNL     1      -0.994   0.369   2.217  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5    6   18
CONECT    5   19
CONECT    6    7    7   11
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   24
END
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SMILES for #<Metabolite:0x00007f9ac9285058>

CNCC(O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007f9ac9285058>

InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
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Synonyms
ValueSource
(+-)-alpha-((Methylamino)methyl)benzenemethanolChEBI
(+-)-HalostachineChEBI
alpha-[(Methylamino)methyl]-benzyl alcoholKegg
(+-)-a-((Methylamino)methyl)benzenemethanolGenerator
(+-)-Α-((methylamino)methyl)benzenemethanolGenerator
a-[(Methylamino)methyl]-benzyl alcoholGenerator
Α-[(methylamino)methyl]-benzyl alcoholGenerator
MPEOAMeSH
N-Methylphenylethanolamine hydrochlorideMeSH
N-Methylphenylethanolamine hydrochloride, (+-)-isomerMeSH
N-Methylphenylethanolamine, (+-)-isomerMeSH
N-Methylphenylethanolamine, (R)-isomerMeSH
2-(methylamino)-1-PhenylethanolHMDB
2-methylamino-1-PhenylethanolHMDB
alpha-((methylamino)Methyl)-DL-benzyl alcoholHMDB
alpha-(Methylaminomethyl)benzyl alcoholHMDB
DL-alpha-(Methylaminomethyl)benzyl alcoholHMDB
HalostachineHMDB
Molecular FormulaC9H13NO
Average Mass151.2056
Monoisotopic Mass151.099714043
IUPAC Name2-(methylamino)-1-phenylethan-1-ol
Traditional Namehalostachine
CAS Registry NumberNot Available
SMILES
CNCC(O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3
InChI KeyZCTYHONEGJTYQV-UHFFFAOYSA-N