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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:48:30 UTC

Update Date

2022-11-23 22:29:16 UTC

HMDB ID

HMDB0254474

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mescaline

Description

mescaline, also known as TMPEA, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. mescaline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on mescaline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mescaline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mescaline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254474
     RDKit          3D
mescaline
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.2678   -2.7071   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -1.3974   -0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033   -0.5849   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -1.0166   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686   -0.2186   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -0.6673   -0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577   -1.3219    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397   -1.7309    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    1.0531    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218    1.5322    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906    2.8327    0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    3.6753    1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561    0.6952   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9788    1.1695   -0.0206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    0.9543    1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -2.7859   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510   -3.4422   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.0382   -1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.0199   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.1941   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -1.3595   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647   -2.2756    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.7195    1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -1.5494   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.3599    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    1.6762    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    3.6478    0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332    3.3860    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    4.7358    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    0.3070    1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    0.4217    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0161    1.9138    1.6114 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  1  0
  6  7  1  0
  7  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END


  Mrv1533004241516042D          

 15 15  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 O   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
    1.4289    0.8250    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
    0.0000    0.8250    0.0000 C   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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254474

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CCN)=CC(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

> <INCHI_KEY>
RHCSKNNOAZULRK-UHFFFAOYSA-N

> <FORMULA>
C11H17NO3

> <MOLECULAR_WEIGHT>
211.261

> <EXACT_MASS>
211.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.102328678294015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4,5-trimethoxyphenyl)ethan-1-amine

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
0.91466166

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.773574841239842

> <JCHEM_POLAR_SURFACE_AREA>
53.71000000000001

> <JCHEM_REFRACTIVITY>
58.676

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mescaline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254474
     RDKit          3D
mescaline
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.2678   -2.7071   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -1.3974   -0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033   -0.5849   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -1.0166   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686   -0.2186   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -0.6673   -0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577   -1.3219    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397   -1.7309    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    1.0531    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218    1.5322    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906    2.8327    0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    3.6753    1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561    0.6952   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9788    1.1695   -0.0206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    0.9543    1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -2.7859   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510   -3.4422   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.0382   -1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.0199   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.1941   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -1.3595   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647   -2.2756    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.7195    1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -1.5494   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.3599    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    1.6762    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    3.6478    0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332    3.3860    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    4.7358    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    0.3070    1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    0.4217    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0161    1.9138    1.6114 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  1  0
  6  7  1  0
  7  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   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       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0254474
HETATM    1  C1  UNL     1      -2.268  -2.707  -1.413  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.480  -1.397  -0.941  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.403  -0.585  -0.580  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.096  -1.017  -0.667  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.969  -0.219  -0.312  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.384  -0.667  -0.398  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.858  -1.322   0.871  1.00  0.00           C  
HETATM    8  N1  UNL     1       4.240  -1.731   0.713  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.671   1.053   0.141  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.622   1.532   0.246  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.891   2.833   0.711  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.185   3.675   1.083  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.656   0.695  -0.122  1.00  0.00           C  
HETATM   14  O3  UNL     1      -2.979   1.170  -0.021  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.661   0.954   1.207  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.420  -2.786  -2.113  1.00  0.00           H  
HETATM   17  H2  UNL     1      -2.151  -3.442  -0.577  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.178  -3.038  -1.978  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.132  -2.020  -1.024  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.042   0.194  -0.619  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.438  -1.359  -1.262  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.265  -2.276   0.983  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.714  -0.719   1.762  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.616  -1.549  -0.229  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.847  -1.360   1.474  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.519   1.676   0.419  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.008   3.648   0.334  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.633   3.386   2.056  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.133   4.736   1.137  1.00  0.00           H  
HETATM   30  H15 UNL     1      -4.552   0.307   1.072  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.016   0.422   1.948  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.016   1.914   1.611  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   19
CONECT    5    6    9    9
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8   24   25
CONECT    9   10   26
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   27   28   29
CONECT   13   14
CONECT   14   15
CONECT   15   30   31   32
END

HMDB0254474
     RDKit          3D
mescaline
 32 32  0  0  0  0  0  0  0  0999 V2000
   -2.2678   -2.7071   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4796   -1.3974   -0.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033   -0.5849   -0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964   -1.0166   -0.6666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9686   -0.2186   -0.3119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3840   -0.6673   -0.3982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577   -1.3219    0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397   -1.7309    0.7128 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    1.0531    0.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6218    1.5322    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8906    2.8327    0.7111 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853    3.6753    1.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6561    0.6952   -0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9788    1.1695   -0.0206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613    0.9543    1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4199   -2.7859   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510   -3.4422   -0.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -3.0382   -1.9780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1323   -2.0199   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    0.1941   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -1.3595   -1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2647   -2.2756    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7140   -0.7195    1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163   -1.5494   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469   -1.3599    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    1.6762    0.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    3.6478    0.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332    3.3860    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326    4.7358    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5518    0.3070    1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0161    0.4217    1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0161    1.9138    1.6114 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  1  0
  6  7  1  0
  7  8  1  0
  5  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13  3  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  4 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Amino-2-(3,4,5-trimethoxyphenyl)ethane	ChEBI
3,4,5-Trimethoxybenzeneethanamine	ChEBI
3,4,5-Trimethoxyphenethylamine	ChEBI
3,4,5-Trimethoxyphenylethylamine	ChEBI
Mescalin	ChEBI
Mescalina	ChEBI
Meskalin	ChEBI
Mezcalina	ChEBI
TMPEA	ChEBI
Mezcalin	MeSH
Peyote	MeSH
Trimethoxyphenethylamine	MeSH

Chemical Formula

C₁₁H₁₇NO₃

Average Molecular Weight

211.261

Monoisotopic Molecular Weight

211.120843411

IUPAC Name

2-(3,4,5-trimethoxyphenyl)ethan-1-amine

Traditional Name

mescaline

CAS Registry Number

Not Available

SMILES

COC1=CC(CCN)=CC(OC)=C1OC

InChI Identifier

InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3

InChI Key

RHCSKNNOAZULRK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Phenethylamines

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amino compound (CHEBI:28346 )
phenethylamine alkaloid (CHEBI:28346 )
methoxybenzene (CHEBI:28346 )
Tyramine derivatives (C06546 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.91	ALOGPS
logP	0.91	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	53.71 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.68 m³·mol⁻¹	ChemAxon
Polarizability	23.1 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
DeepCCS	[M+H]+	142.459	30932474
DeepCCS	[M-H]-	139.621	30932474
DeepCCS	[M-2H]-	176.124	30932474
DeepCCS	[M+Na]+	151.662	30932474
AllCCS	[M+H]+	148.3	32859911
AllCCS	[M+H-H2O]+	144.3	32859911
AllCCS	[M+NH4]+	152.0	32859911
AllCCS	[M+Na]+	153.1	32859911
AllCCS	[M-H]-	150.2	32859911
AllCCS	[M+Na-2H]-	151.0	32859911
AllCCS	[M+HCOO]-	152.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
mescaline	COC1=CC(CCN)=CC(OC)=C1OC	2550.8	Standard polar	33892256
mescaline	COC1=CC(CCN)=CC(OC)=C1OC	1815.6	Standard non polar	33892256
mescaline	COC1=CC(CCN)=CC(OC)=C1OC	1707.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
mescaline,1TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC	1840.6	Semi standard non polar	33892256
mescaline,1TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC	1948.9	Standard non polar	33892256
mescaline,1TMS,isomer #1	COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC	2514.7	Standard polar	33892256
mescaline,2TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2079.6	Semi standard non polar	33892256
mescaline,2TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2120.9	Standard non polar	33892256
mescaline,2TMS,isomer #1	COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC	2419.8	Standard polar	33892256
mescaline,1TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2084.6	Semi standard non polar	33892256
mescaline,1TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2134.6	Standard non polar	33892256
mescaline,1TBDMS,isomer #1	COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2572.6	Standard polar	33892256
mescaline,2TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2513.6	Semi standard non polar	33892256
mescaline,2TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2497.9	Standard non polar	33892256
mescaline,2TBDMS,isomer #1	COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC	2556.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Mescaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6910000000-63b875b68510f431304a	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mescaline 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 10V, Positive-QTOF	splash10-03dj-0890000000-616863bde223b3ac872c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 20V, Positive-QTOF	splash10-0002-0920000000-47fd07c5573212e7fc36	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 40V, Positive-QTOF	splash10-014i-5900000000-15a76f5868097c4890ed	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 10V, Negative-QTOF	splash10-03di-0090000000-fd2ca69e6cdbbf1a0a0c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 20V, Negative-QTOF	splash10-03di-0890000000-83e2781633dd51c42f35	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 40V, Negative-QTOF	splash10-000i-2900000000-67896f160b9a42f4f333	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 10V, Positive-QTOF	splash10-0002-0910000000-9a24a439b17db5331dfb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 20V, Positive-QTOF	splash10-0002-0900000000-501fa4dae613a2963687	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 40V, Positive-QTOF	splash10-0ktb-3900000000-7dc0298d7f673f65aa0f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 10V, Negative-QTOF	splash10-03di-0090000000-f0203d0d15365b0c0653	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 20V, Negative-QTOF	splash10-03di-0590000000-c63f9b5dcd00541ee2ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mescaline 40V, Negative-QTOF	splash10-0aor-9400000000-76523f7fb050748dbc11	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00001419

Chemspider ID

3934

KEGG Compound ID

C06546

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mescaline

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28346

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

Enzyme Details

2. 5-hydroxytryptamine receptor 2A

General function:: Not Available
Specific function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:: HTR2A
Uniprot ID:: Q5R4Q6
Molecular weight:: 52528.45

Enzyme Details

3. 5-hydroxytryptamine receptor 2A

General function:: Not Available
Specific function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:: HTR2A
Uniprot ID:: P50128
Molecular weight:: 52602.58

Enzyme Details

4. 5-hydroxytryptamine receptor 2A

General function:: Not Available
Specific function:: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:: HTR2A
Uniprot ID:: P50129
Molecular weight:: 52675.595

Showing metabocard for Mescaline (HMDB0254474)

MOL for HMDB0254474 (Mescaline)

3D MOL for HMDB0254474 (Mescaline)

3D SDF for HMDB0254474 (Mescaline)

3D-SDF for HMDB0254474 (Mescaline)

PDB for HMDB0254474 (Mescaline)

3D PDB for HMDB0254474 (Mescaline)

SMILES for HMDB0254474 (Mescaline)

INCHI for HMDB0254474 (Mescaline)

Structure for HMDB0254474 (Mescaline)

3D Structure for HMDB0254474 (Mescaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes