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Showing NP-Card for 3-Methoxytyramine (NP0001274)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:42:06 UTC
NP-MRD IDNP0001274
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methoxytyramine
Description3-Methoxytyramine, also known as 4-(2-amino-Ethyl)-2-methoxy-phenol or 3-O-Methyldopamine, is classified as a member of the Methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-Methoxytyramine is considered to be slightly soluble (in water) and acidic. 3-Methoxytyramine can be found primarily in human brain and most tissues tissues; and in blood, cerebrospinal fluid (csf) or urine. Within a cell, 3-methoxytyramine is primarily located in the cytoplasm
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001274 (3-Methoxytyramine)

3-Methoxytyramine.mol
  Mrv1652303182019222D          

 12 12  0  0  0  0            999 V2000
    2.5006   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 11 12  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0001274 (3-Methoxytyramine)

HMDB0000022
     RDKit          3D
3-Methoxytyramine
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.8295   -1.8214    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479   -0.5750   -0.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.0922   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5498   -0.4846   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    0.1554   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347   -0.4367   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3610    0.0498    1.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553   -0.4859    1.5007 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449    1.3720   -1.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    1.9631   -1.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8334    1.3124   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0910    1.8876   -1.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727   -2.2108    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3118   -1.6649    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -2.5295   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -1.4705    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102   -1.5333   -0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -0.0914   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.3195    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    1.1560    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562    0.2159    2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -0.8074    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    1.9213   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    2.9242   -1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    1.3811   -1.0110 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  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
M  END
Download

3D SDF for NP0001274 (3-Methoxytyramine)

3-Methoxytyramine.mol
  Mrv1652303182019222D          

 12 12  0  0  0  0            999 V2000
    2.5006   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
 11 12  1  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(CCN)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3

> <INCHI_KEY>
DIVQKHQLANKJQO-UHFFFAOYSA-N

> <FORMULA>
C9H13NO2

> <MOLECULAR_WEIGHT>
167.205

> <EXACT_MASS>
167.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
18.214012386605404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2-aminoethyl)-2-methoxyphenol

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
0.5270476997828332

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.389796021053263

> <JCHEM_PKA_STRONGEST_BASIC>
9.642266949651177

> <JCHEM_POLAR_SURFACE_AREA>
55.480000000000004

> <JCHEM_REFRACTIVITY>
47.7305

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methoxytyramine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001274 (3-Methoxytyramine)

HMDB0000022
     RDKit          3D
3-Methoxytyramine
 25 25  0  0  0  0  0  0  0  0999 V2000
   -2.8295   -1.8214    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9479   -0.5750   -0.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.0922   -0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5498   -0.4846   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6048    0.1554   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9347   -0.4367   -0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3610    0.0498    1.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6553   -0.4859    1.5007 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5449    1.3720   -1.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    1.9631   -1.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8334    1.3124   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0910    1.8876   -1.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8727   -2.2108    0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3118   -1.6649    1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373   -2.5295   -0.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316   -1.4705    0.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102   -1.5333   -0.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -0.0914   -1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888   -0.3195    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4267    1.1560    1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1562    0.2159    2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1502   -0.8074    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4443    1.9213   -1.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    2.9242   -1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    1.3811   -1.0110 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  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 12 25  1  0
M  END
Download

PDB for NP0001274 (3-Methoxytyramine)

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Methoxytyramine.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  N   UNK     0       4.668  -1.540   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.334   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.334  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.668  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
CONECT   11   12    6                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
Download

3D PDB for NP0001274 (3-Methoxytyramine)

COMPND    HMDB0000022
HETATM    1  C1  UNL     1      -2.830  -1.821   0.600  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.948  -0.575  -0.034  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.767   0.092  -0.403  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.550  -0.485  -0.136  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.605   0.155  -0.490  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.935  -0.437  -0.219  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.361   0.050   1.159  1.00  0.00           C  
HETATM    8  N1  UNL     1       3.655  -0.486   1.501  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.545   1.372  -1.110  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.670   1.963  -1.384  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.833   1.312  -1.024  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.091   1.888  -1.289  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.873  -2.211   0.734  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.312  -1.665   1.557  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.237  -2.529  -0.050  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.532  -1.471   0.367  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.810  -1.533  -0.237  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.632  -0.091  -1.004  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.589  -0.320   1.873  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.427   1.156   1.157  1.00  0.00           H  
HETATM   21  H9  UNL     1       4.156   0.216   2.072  1.00  0.00           H  
HETATM   22  H10 UNL     1       4.150  -0.807   0.658  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.444   1.921  -1.412  1.00  0.00           H  
HETATM   24  H12 UNL     1      -0.750   2.924  -1.873  1.00  0.00           H  
HETATM   25  H13 UNL     1      -3.917   1.381  -1.011  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    9    9
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8   21   22
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12
CONECT   12   25
END
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SMILES for NP0001274 (3-Methoxytyramine)

COC1=C(O)C=CC(CCN)=C1
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INCHI for NP0001274 (3-Methoxytyramine)

InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
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View in JSmol
Synonyms
ValueSource
3-Methoxy-4-hydroxyphenylethyl amineHMDB
3-O-MethyldopamineHMDB
4-(2-Amino-ethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxy-phenolHMDB
4-(2-Aminoethyl)-2-methoxyphenolHMDB
5-(2-Aminoethyl)guaiacolHMDB
MethoxytyramineHMDB
3-Methoxytyramine hydrochlorideHMDB
Chemical FormulaC9H13NO2
Average Mass167.2050 Da
Monoisotopic Mass167.09463 Da
IUPAC Name4-(2-aminoethyl)-2-methoxyphenol
Traditional Namemethoxytyramine
CAS Registry Number554-52-9
SMILES
COC1=C(O)C=CC(CCN)=C1
InChI Identifier
InChI=1S/C9H13NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4-5,10H2,1H3
InChI KeyDIVQKHQLANKJQO-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acacia rigidula Benth.KNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Austrocylindropuntia cylindricaLOTUS Database
Backebergia militarisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cylindropuntia imbricataLOTUS Database
Dromaius novaehollandiaeFooDB
Echinopsis spachianaLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lyallia kerguelensisLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
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Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenethylamine
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 2-arylethylamine
  • Aralkylamine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.08Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
PropertyValueSource
Water Solubility5.36 g/LALOGPS
logP-0.04ALOGPS
logP0.53ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)10.39ChemAxon
pKa (Strongest Basic)9.64ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area55.48 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.73 m³·mol⁻¹ChemAxon
Polarizability18.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000022
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021876
KNApSAcK IDC00042132
Chemspider ID1606
KEGG Compound IDC05587
BioCyc IDNot Available
BiGG ID46076
Wikipedia Link3-Methoxytyramine
METLIN ID5094
PubChem Compound1669
PDB IDNot Available
ChEBI ID742324
Good Scents IDNot Available
References
General References
  1. Leysen JE, Wynants J, Eens A, Janssen PA: Ketanserin reduces a particular monoamine pool in peripheral tissues. Mol Pharmacol. 1989 Mar;35(3):375-80. [PubMed:2927387 ]
  2. Faraj BA, Lawson DH, Nixon DW, Murray DR, Camp VM, Ali FM, Black M, Stacciarini W, Tarcan Y: Melanoma detection by enzyme-radioimmunoassay of L-dopa, dopamine, and 3-O-methyldopamine in urine. Clin Chem. 1981 Jan;27(1):108-12. [PubMed:7004664 ]
  3. Muskiet FA, Thomasson CG, Gerding AM, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of catecholamines and their 3-O-methylated metabolites in urine by mass fragmentography with use of deuterated internal standards. Clin Chem. 1979 Mar;25(3):453-60. [PubMed:262188 ]
  4. Sparks DL, Hunsaker JC 3rd, Slevin JT: Postmortem accumulation of 3-methoxytyramine in the brain. N Engl J Med. 1984 Aug 23;311(8):540. [PubMed:6749220 ]
  5. Peterson ZD, Collins DC, Bowerbank CR, Lee ML, Graves SW: Determination of catecholamines and metanephrines in urine by capillary electrophoresis-electrospray ionization-time-of-flight mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 5;776(2):221-9. [PubMed:12138004 ]
  6. Beck O, Faull KF: Extractive acylation and mass spectrometric assay of 3-methoxytyramine, normetanephrine, and metanephrine in cerebrospinal fluid. Anal Biochem. 1985 Sep;149(2):492-500. [PubMed:4073504 ]
  7. Oeltmann T, Carson R, Shannon JR, Ketch T, Robertson D: Assessment of O-methylated catecholamine levels in plasma and urine for diagnosis of autonomic disorders. Auton Neurosci. 2004 Nov 30;116(1-2):1-10. [PubMed:15556832 ]
  8. Yui K, Ikemoto S, Goto K: Factors for susceptibility to episode recurrence in spontaneous recurrence of methamphetamine psychosis. Ann N Y Acad Sci. 2002 Jun;965:292-304. [PubMed:12105105 ]
  9. Uchikura K, Horikawa R, Tanimura T, Kabasawa Y: Determination of catecholamines by radioenzymatic assay using ion-pair liquid chromatography. J Chromatogr. 1981 Apr 10;223(1):41-50. [PubMed:7251775 ]
  10. Carlsson A, Lindqvist M, Kehr W: Postmortal accumulation of 3-methoxytyramine in brain. Naunyn Schmiedebergs Arch Pharmacol. 1974;284(4):365-72. [PubMed:4281061 ]
  11. Shoup RE, Kissinger PT: Determination of urinary normetanephrine, metanephrine, and 3-methoxytyramine by liquid chromatography, with amperometric detection. Clin Chem. 1977 Jul;23(7):1268-74. [PubMed:872373 ]
  12. Wester P, Puu G, Reiz S, Winblad B, Wester PO: Increased monoamine metabolite concentrations and cholinesterase activities in cerebrospinal fluid of patients with acute stroke. Acta Neurol Scand. 1987 Dec;76(6):473-9. [PubMed:3434205 ]
  13. Yui K, Goto K, Ikemoto S: The role of noradrenergic and dopaminergic hyperactivity in the development of spontaneous recurrence of methamphetamine psychosis and susceptibility to episode recurrence. Ann N Y Acad Sci. 2004 Oct;1025:296-306. [PubMed:15542730 ]
  14. Rajput AH, Fenton ME, Di Paolo T, Sitte H, Pifl C, Hornykiewicz O: Human brain dopamine metabolism in levodopa-induced dyskinesia and wearing-off. Parkinsonism Relat Disord. 2004 Jun;10(4):221-6. [PubMed:15120096 ]