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Showing metabocard for 3,4-Dimethoxyphenylethylamine (HMDB0041806)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:40:09 UTC
Update Date2023-02-21 17:28:57 UTC
HMDB IDHMDB0041806
Secondary Accession Numbers
  • HMDB41806
Metabolite Identification
Common Name3,4-Dimethoxyphenylethylamine
Description3,4-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
Data?1677000537
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0041806 (3,4-Dimethoxyphenylethylamine)


  Mrv1652304062013042D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  9  1  0  0  0  0
 13  2  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
Download

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

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
Download

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


  Mrv1652304062013042D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  9  1  0  0  0  0
 13  2  1  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041806

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H15NO2

> <MOLECULAR_WEIGHT>
181.2316

> <EXACT_MASS>
181.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.181820995347508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)ethan-1-amine

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
1.0723329256666672

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.796271230904013

> <JCHEM_POLAR_SURFACE_AREA>
44.480000000000004

> <JCHEM_REFRACTIVITY>
52.21280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dimethoxyphenylethylamine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

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

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
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PDB for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

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

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
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SMILES for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

COC1=C(OC)C=C(CCN)C=C1
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INCHI for HMDB0041806 (3,4-Dimethoxyphenylethylamine)

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
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Synonyms
ValueSource
2-(3,4-Dimethoxy-phenyl)-ethylamineChEBI
3,4-Di-O-methyldopamineChEBI
3,4-Dimethoxy-beta-phenylethylamineChEBI
3,4-DimethoxybenzeneethanamineChEBI
3,4-DimethoxydopamineChEBI
3,4-DimethoxyphenethylamineChEBI
beta-(3,4-Dimethyoxyphenyl)ethylamineChEBI
DimethoxydopamineChEBI
DimethoxyphenylethylamineChEBI
DimethylmescalineChEBI
DIMPEAChEBI
DMPEAChEBI
Dopamine dimethyl etherChEBI
HomoveratrylamineChEBI
O,O-DimethyldopamineChEBI
3,4-Dimethoxy-b-phenylethylamineGenerator
3,4-Dimethoxy-β-phenylethylamineGenerator
b-(3,4-Dimethyoxyphenyl)ethylamineGenerator
Β-(3,4-dimethyoxyphenyl)ethylamineGenerator
2-(3,4-Dimethoxyphenyl)ethanamineHMDB
2-(3,4-Dimethoxyphenyl)ethanamine (acd/name 4.0)HMDB
2-(3,4-Dimethoxyphenyl)ethylamineHMDB
2-(3,4-Dimethoxyphenyl)ethylamine (acd/name 4.0)HMDB
3, 4-Dimethoxy-beta-phenethylamineHMDB
3, 4-Dimethoxy-beta-phenylethylamineHMDB
3, 4-DimethoxybenzeneethanamineHMDB
3, 4-DimethoxyphenethylamineHMDB
3, 4-Dimethoxyphenylethylamine(base)HMDB
3,4-Dimethoxy-benzeneethanamineHMDB
3,4-Dimethoxy-benzenethanamineHMDB
3,4-Dimethoxy-beta-phenethylamineHMDB
3,4-Dimethoxy-phenethylamineHMDB
3,4-DimethoxypheneethylamineHMDB
3,4-Dimethoxyphenylethylamine(base)HMDB
beta-(3,4-Dimethoxyphenyl)ethylamineHMDB
DMPEHMDB
Chemical FormulaC10H15NO2
Average Molecular Weight181.2316
Monoisotopic Molecular Weight181.110278729
IUPAC Name2-(3,4-dimethoxyphenyl)ethan-1-amine
Traditional Namedimethoxyphenylethylamine
CAS Registry Number120-20-7
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 KeyANOUKFYBOAKOIR-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point163 - 165 °CNot Available
Water SolubilityNot AvailableNot Available
LogP0.77Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
logP0.9ALOGPS
logP1.07ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.21 m³·mol⁻¹ChemAxon
Polarizability20.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.47731661259
DarkChem[M-H]-139.4131661259
DeepCCS[M+H]+140.11530932474
DeepCCS[M-H]-136.83630932474
DeepCCS[M-2H]-173.94430932474
DeepCCS[M+Na]+149.48230932474
AllCCS[M+H]+140.632859911
AllCCS[M+H-H2O]+136.432859911
AllCCS[M+NH4]+144.632859911
AllCCS[M+Na]+145.732859911
AllCCS[M-H]-142.532859911
AllCCS[M+Na-2H]-143.532859911
AllCCS[M+HCOO]-144.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 2.3 minutes32390414
Predicted by Siyang on May 30, 20229.6605 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.09 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid129.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid812.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid289.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid122.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid176.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid69.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid280.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid292.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)644.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid726.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid240.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid749.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid197.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid249.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate510.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA419.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water75.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-DimethoxyphenylethylamineCOC1=C(OC)C=C(CCN)C=C12377.3Standard polar33892256
3,4-DimethoxyphenylethylamineCOC1=C(OC)C=C(CCN)C=C11577.6Standard non polar33892256
3,4-DimethoxyphenylethylamineCOC1=C(OC)C=C(CCN)C=C11571.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethoxyphenylethylamine,1TMS,isomer #1COC1=CC=C(CCN[Si](C)(C)C)C=C1OC1706.2Semi standard non polar33892256
3,4-Dimethoxyphenylethylamine,1TMS,isomer #1COC1=CC=C(CCN[Si](C)(C)C)C=C1OC1779.1Standard non polar33892256
3,4-Dimethoxyphenylethylamine,2TMS,isomer #1COC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OC1949.1Semi standard non polar33892256
3,4-Dimethoxyphenylethylamine,2TMS,isomer #1COC1=CC=C(CCN([Si](C)(C)C)[Si](C)(C)C)C=C1OC1996.0Standard non polar33892256
3,4-Dimethoxyphenylethylamine,1TBDMS,isomer #1COC1=CC=C(CCN[Si](C)(C)C(C)(C)C)C=C1OC1954.5Semi standard non polar33892256
3,4-Dimethoxyphenylethylamine,1TBDMS,isomer #1COC1=CC=C(CCN[Si](C)(C)C(C)(C)C)C=C1OC1985.3Standard non polar33892256
3,4-Dimethoxyphenylethylamine,2TBDMS,isomer #1COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC2377.3Semi standard non polar33892256
3,4-Dimethoxyphenylethylamine,2TBDMS,isomer #1COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC2378.1Standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111666
KNApSAcK IDC00042105
Chemspider ID8114
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3,4-dimethoxyphenethylamine
METLIN IDNot Available
PubChem Compound8421
PDB IDNot Available
ChEBI ID136995
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]