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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:40:09 UTC

Update Date

2023-02-21 17:28:57 UTC

HMDB ID

HMDB0041806

Secondary Accession Numbers

HMDB41806

Metabolite Identification

Common Name

3,4-Dimethoxyphenylethylamine

Description

3,4-Dimethoxyphenylethylamine, also known as 3,4-DMPEA or DMPEA is an endogenous metabolite found in urine that belongs to both the phenethylamine and catecholamine families. DMPEA is an analogue of dopamine (3,4-dihydroxyphenethylamine), with a substitution of the hydroxy groups with methoxy groups. DMPEA is also structurally similar to mescaline (3,4,5-trimethoxyphenylethylamine) and occurs naturally alongside it in various species of cacti such as the San Pedro and Peruvian Torch (PMID: 5511715 , 925910 , 600028 ). DMPEA received wide attention after it was proposed as a biomarker in schizophrenic patients urine, however later studies revealed that DMPEA is also excreted by non-schizophrenics (PMID: 709888 ). DMPEA has little known bioactivity, but it has some action as a monoamine oxidase inhibitor (PMID: 886445 ). DMPEA has also been shown to have neurotoxic effects, especially in the nigrostriatal system and among dopaminergic neurons (PMID: 9409711 , 9134983 ). DMPEA appears to be an inhibitor of mitochondrial complex I (PMID: 9409711 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0041806
     RDKit          3D
3,4-Dimethoxyphenylethylamine
 28 28  0  0  0  0  0  0  0  0999 V2000
   -3.9190   -1.7061    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.4562    0.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.4339    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610   -1.5850    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010   -1.6129   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8399   -0.4329   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -0.4089   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -0.1287    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.1028    0.5891 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    0.7396   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    0.7306   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    1.9264   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.1449   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9531   -1.6051    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499   -2.3897   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.1265    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -2.5165    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767   -2.5317    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -1.4138   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2996   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.8245    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994   -0.9483    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.2299   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970    0.7490    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889    1.6588   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    3.0852   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    3.8847   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    3.5852    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
M  END

HMDB0041806
     RDKit          3D
3,4-Dimethoxyphenylethylamine
 28 28  0  0  0  0  0  0  0  0999 V2000
   -3.9190   -1.7061    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.4562    0.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.4339    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610   -1.5850    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010   -1.6129   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8399   -0.4329   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -0.4089   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -0.1287    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.1028    0.5891 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    0.7396   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    0.7306   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    1.9264   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.1449   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9531   -1.6051    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499   -2.3897   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.1265    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -2.5165    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767   -2.5317    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -1.4138   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2996   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.8245    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994   -0.9483    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.2299   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970    0.7490    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889    1.6588   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    3.0852   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    3.8847   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    3.5852    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    8   10                                                       
CONECT    8    3    5    7                                                  
CONECT    9    4   10   12                                                  
CONECT   10    7    9   13                                                  
CONECT   11    6                                                            
CONECT   12    1    9                                                       
CONECT   13    2   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0041806
HETATM    1  C1  UNL     1      -3.919  -1.706   0.564  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.319  -0.456   0.238  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.933  -0.434   0.038  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.161  -1.585   0.150  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.201  -1.613  -0.037  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.840  -0.433  -0.355  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.311  -0.409  -0.568  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.956  -0.129   0.786  1.00  0.00           C  
HETATM    9  N1  UNL     1       4.400  -0.103   0.589  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.085   0.740  -0.474  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.276   0.731  -0.279  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.957   1.926  -0.413  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.364   3.145  -0.732  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.953  -1.605   0.889  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.750  -2.390  -0.270  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.354  -2.126   1.446  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.648  -2.516   0.398  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.777  -2.532   0.058  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.663  -1.414  -0.874  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.636   0.300  -1.327  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.596   0.824   1.193  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.699  -0.948   1.485  1.00  0.00           H  
HETATM   23  H10 UNL     1       4.675  -0.230  -0.393  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.797   0.749   1.044  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.589   1.659  -0.722  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.611   3.085  -1.549  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.113   3.885  -1.062  1.00  0.00           H  
HETATM   28  H15 UNL     1      -0.868   3.585   0.175  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   10
CONECT    7    8   19   20
CONECT    8    9   21   22
CONECT    9   23   24
CONECT   10   11   11   25
CONECT   11   12
CONECT   12   13
CONECT   13   26   27   28
END

HMDB0041806
     RDKit          3D
3,4-Dimethoxyphenylethylamine
 28 28  0  0  0  0  0  0  0  0999 V2000
   -3.9190   -1.7061    0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.4562    0.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334   -0.4339    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1610   -1.5850    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2010   -1.6129   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8399   -0.4329   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3106   -0.4089   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9564   -0.1287    0.7861 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4003   -0.1028    0.5891 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852    0.7396   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2764    0.7306   -0.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    1.9264   -0.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3636    3.1449   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9531   -1.6051    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7499   -2.3897   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3537   -2.1265    1.4463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6475   -2.5165    0.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7767   -2.5317    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6629   -1.4138   -0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6361    0.2996   -1.3269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5960    0.8245    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6994   -0.9483    1.4855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -0.2299   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7970    0.7490    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889    1.6588   -0.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    3.0852   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    3.8847   -1.0621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8679    3.5852    0.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 11  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dimethoxy-phenyl)-ethylamine	ChEBI
3,4-Di-O-methyldopamine	ChEBI
3,4-Dimethoxy-beta-phenylethylamine	ChEBI
3,4-Dimethoxybenzeneethanamine	ChEBI
3,4-Dimethoxydopamine	ChEBI
3,4-Dimethoxyphenethylamine	ChEBI
beta-(3,4-Dimethyoxyphenyl)ethylamine	ChEBI
Dimethoxydopamine	ChEBI
Dimethoxyphenylethylamine	ChEBI
Dimethylmescaline	ChEBI
DIMPEA	ChEBI
DMPEA	ChEBI
Dopamine dimethyl ether	ChEBI
Homoveratrylamine	ChEBI
O,O-Dimethyldopamine	ChEBI
3,4-Dimethoxy-b-phenylethylamine	Generator
3,4-Dimethoxy-β-phenylethylamine	Generator
b-(3,4-Dimethyoxyphenyl)ethylamine	Generator
Β-(3,4-dimethyoxyphenyl)ethylamine	Generator
2-(3,4-Dimethoxyphenyl)ethanamine	HMDB
2-(3,4-Dimethoxyphenyl)ethanamine (acd/name 4.0)	HMDB
2-(3,4-Dimethoxyphenyl)ethylamine	HMDB
2-(3,4-Dimethoxyphenyl)ethylamine (acd/name 4.0)	HMDB
3, 4-Dimethoxy-beta-phenethylamine	HMDB
3, 4-Dimethoxy-beta-phenylethylamine	HMDB
3, 4-Dimethoxybenzeneethanamine	HMDB
3, 4-Dimethoxyphenethylamine	HMDB
3, 4-Dimethoxyphenylethylamine(base)	HMDB
3,4-Dimethoxy-benzeneethanamine	HMDB
3,4-Dimethoxy-benzenethanamine	HMDB
3,4-Dimethoxy-beta-phenethylamine	HMDB
3,4-Dimethoxy-phenethylamine	HMDB
3,4-Dimethoxypheneethylamine	HMDB
3,4-Dimethoxyphenylethylamine(base)	HMDB
beta-(3,4-Dimethoxyphenyl)ethylamine	HMDB
DMPE	HMDB

Chemical Formula

C₁₀H₁₅NO₂

Average Molecular Weight

181.2316

Monoisotopic Molecular Weight

181.110278729

IUPAC Name

2-(3,4-dimethoxyphenyl)ethan-1-amine

Traditional Name

dimethoxyphenylethylamine

CAS Registry Number

120-20-7

SMILES

COC1=C(OC)C=C(CCN)C=C1

InChI Identifier

InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3

InChI Key

ANOUKFYBOAKOIR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

O-dimethoxybenzene
Dimethoxybenzene
Phenethylamine
Phenoxy compound
Anisole
2-arylethylamine
Phenol ether
Alkyl aryl ether
Aralkylamine
Ether
Organic nitrogen compound
Primary amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:136995 )
alkaloid (CHEBI:136995 )
phenylethylamine (CHEBI:136995 )

Ontology

Not Available

Endogenous (HMDB: HMDB0041806)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	163 - 165 °C	Not Available
Water Solubility	Not Available	Not Available
LogP	0.77	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	0.9	ALOGPS
logP	1.07	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.48 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.21 m³·mol⁻¹	ChemAxon
Polarizability	20.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.477	31661259
DarkChem	[M-H]-	139.41	31661259
DeepCCS	[M+H]+	140.115	30932474
DeepCCS	[M-H]-	136.836	30932474
DeepCCS	[M-2H]-	173.944	30932474
DeepCCS	[M+Na]+	149.482	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.4	32859911
AllCCS	[M+NH4]+	144.6	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	142.5	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	144.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethoxyphenylethylamine	COC1=C(OC)C=C(CCN)C=C1	2377.3	Standard polar	33892256
3,4-Dimethoxyphenylethylamine	COC1=C(OC)C=C(CCN)C=C1	1577.6	Standard non polar	33892256
3,4-Dimethoxyphenylethylamine	COC1=C(OC)C=C(CCN)C=C1	1571.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethoxyphenylethylamine,1TMS,isomer #1	COC1=CC=C(CCN[Si](C)(C)C)C=C1OC	1706.2	Semi standard non polar	33892256
3,4-Dimethoxyphenylethylamine,1TMS,isomer #1	COC1=CC=C(CCN[Si](C)(C)C)C=C1OC	1779.1	Standard non polar	33892256
3,4-Dimethoxyphenylethylamine,2TMS,isomer #1	COC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OC	1949.1	Semi standard non polar	33892256
3,4-Dimethoxyphenylethylamine,2TMS,isomer #1	COC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OC	1996.0	Standard non polar	33892256
3,4-Dimethoxyphenylethylamine,1TBDMS,isomer #1	COC1=CC=C(CCN[Si](C)(C)C(C)(C)C)C=C1OC	1954.5	Semi standard non polar	33892256
3,4-Dimethoxyphenylethylamine,1TBDMS,isomer #1	COC1=CC=C(CCN[Si](C)(C)C(C)(C)C)C=C1OC	1985.3	Standard non polar	33892256
3,4-Dimethoxyphenylethylamine,2TBDMS,isomer #1	COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	2377.3	Semi standard non polar	33892256
3,4-Dimethoxyphenylethylamine,2TBDMS,isomer #1	COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	2378.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-7900000000-e258dc3dc0a069f89bd5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-7900000000-120c686cfb57062addf9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-8900000000-7b3bb96b7d3241d758d7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-7900000000-e258dc3dc0a069f89bd5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-7900000000-120c686cfb57062addf9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine EI-B (Non-derivatized)	splash10-0ue9-8900000000-7b3bb96b7d3241d758d7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6900000000-38d3389596ede8e365b3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethoxyphenylethylamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine , positive-QTOF	splash10-014i-0900000000-adbc40a8a0427b3f3fce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 35V, Positive-QTOF	splash10-0gb9-1900000000-378f4a1c05d1e1ae78af	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 10V, Positive-QTOF	splash10-00lr-0900000000-25ceec6a941bb2399272	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 20V, Positive-QTOF	splash10-014i-0900000000-9a1f680719d4d377cf0c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 40V, Positive-QTOF	splash10-059b-7900000000-ea4cd6aaee62c9a9dcf0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 10V, Negative-QTOF	splash10-001i-0900000000-5499743e5a06328defcd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 20V, Negative-QTOF	splash10-001i-0900000000-0ca8775e2ab7549a7dd6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 40V, Negative-QTOF	splash10-0a4i-4900000000-f6e4dbf7311ac479604d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 10V, Negative-QTOF	splash10-001i-0900000000-ae9b23b219381cfbd573	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 20V, Negative-QTOF	splash10-001j-0900000000-1d498454bd777cb50d22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 40V, Negative-QTOF	splash10-00l6-9600000000-588efb293ab7f45b2f0e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 10V, Positive-QTOF	splash10-014i-0900000000-768c86e8875032c5d486	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 20V, Positive-QTOF	splash10-014i-0900000000-f77b2997745c83d2f0e7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethoxyphenylethylamine 40V, Positive-QTOF	splash10-001r-4900000000-4be1f0b7a8cf6ab03b8b	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB111666

KNApSAcK ID

C00042105

Chemspider ID

8114

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

3,4-dimethoxyphenethylamine

METLIN ID

Not Available

PubChem Compound

8421

PDB ID

Not Available

ChEBI ID

136995

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Lundstrom J: Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R. Acta Pharm Suec. 1970 Dec;7(6):651-66. [PubMed:5511715 ]
Pummangura S, Nichols DE, McLaughlin JL: Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii. J Pharm Sci. 1977 Oct;66(10):1485-7. doi: 10.1002/jps.2600661037. [PubMed:925910 ]
Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG: Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus. Lloydia. 1977 Nov-Dec;40(6):585-90. [PubMed:600028 ]
Knoll E, Wisser H, Emrich HM: 3,4-Dimethoxyphenylethylamine excretion of normals and schizophrenics, behaviour during total fasting. Clin Chim Acta. 1978 Nov 1;89(3):493-502. doi: 10.1016/0009-8981(78)90415-1. [PubMed:709888 ]
Keller WJ, Ferguson GG: Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase. J Pharm Sci. 1977 Jul;66(7):1048-50. doi: 10.1002/jps.2600660741. [PubMed:886445 ]
Koshimura I, Imai H, Hidano T, Endo K, Mochizuki H, Kondo T, Mizuno Y: Dimethoxyphenylethylamine and tetrahydropapaverine are toxic to the nigrostriatal system. Brain Res. 1997 Oct 31;773(1-2):108-16. doi: 10.1016/s0006-8993(97)00922-0. [PubMed:9409711 ]
Goto K, Mochizuki H, Hattori T, Nakamura N, Mizuno Y: Neurotoxic effects of papaverine, tetrahydropapaverine and dimethoxyphenylethylamine on dopaminergic neurons in ventral mesencephalic-striatal co-culture. Brain Res. 1997 Apr 18;754(1-2):260-8. doi: 10.1016/s0006-8993(97)00093-0. [PubMed:9134983 ]

Showing metabocard for 3,4-Dimethoxyphenylethylamine (HMDB0041806)

MOL for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

3D MOL for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

3D SDF for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

3D-SDF for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

PDB for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

3D PDB for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

SMILES for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

INCHI for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

Structure for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

3D Structure for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra