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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7) Show 7 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 10:47:12 UTC

Update Date

2023-02-21 17:16:55 UTC

HMDB ID

HMDB0004095

Secondary Accession Numbers

HMDB04095

Metabolite Identification

Common Name

5-Methoxytryptamine

Description

5-Methoxytryptamine, also known as mexamine or 5-MT, belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. It is biosynthesized via the deacetylation of melatonin in the pineal gland. 5-MT acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans. Its affinity for the 5-HT5A receptor is unknown. It has no affinity for the 5-HT3 receptor and is affinity for the 5-HT1E receptor is very weak in comparison to the other 5-HT1 receptors. 5-MT has been shown to occur naturally in the body in low levels.

Structure

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

HMDB0004095
     RDKit          3D
5-Methoxytryptamine
 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.8135    2.3413    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    1.0350    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3401   -0.0314    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577   -1.3181    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.3577    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030   -2.1410    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.9563    0.0193 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052   -2.2586   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -0.9278   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    0.2295   -0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494    1.0858    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.1844   -0.3558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.8694   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.1736    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6964    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025    2.3512   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    3.0234    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -1.4258    1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.3551    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -3.9863    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829   -2.6565   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.8843   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -0.0968   -1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4749    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0868    0.5672    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    2.0488   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953    3.1119   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.1732   -0.1541 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  2  0
 14  3  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
M  END


  Mrv1652305271900002D          

 14 15  0  0  0  0            999 V2000
   25.8762  -12.0742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1203  -10.4968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -13.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8639  -11.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0566  -11.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1617  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8003  -12.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0197  -12.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2818  -12.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -12.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5908  -13.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3052  -13.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 10  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004095

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(NC=C2CCN)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

> <INCHI_KEY>
JTEJPPKMYBDEMY-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O

> <MOLECULAR_WEIGHT>
190.2417

> <EXACT_MASS>
190.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.31855693693656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.3287661843333338

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.44662112135106

> <JCHEM_PKA_STRONGEST_BASIC>
9.760262342114133

> <JCHEM_POLAR_SURFACE_AREA>
51.04

> <JCHEM_REFRACTIVITY>
56.8361

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5 methoxytryptamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004095
     RDKit          3D
5-Methoxytryptamine
 28 29  0  0  0  0  0  0  0  0999 V2000
   -2.8135    2.3413    0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    1.0350    0.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3401   -0.0314    0.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577   -1.3181    0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8810   -2.3577    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6030   -2.1410    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4514   -2.9563    0.0193 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052   -2.2586   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1592   -0.9278   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460    0.2295   -0.9299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4494    1.0858    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.1844   -0.3558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1578   -0.8694   -0.0568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597    0.1736    0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743    2.6964    1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025    2.3512   -0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    3.0234    0.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7752   -1.4258    1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.3551    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879   -3.9863    0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829   -2.6565   -0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    0.8843   -1.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8421   -0.0968   -1.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5669    1.4749    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0868    0.5672    0.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2274    2.0488   -0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953    3.1119   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.1732   -0.1541 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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  2  0
 14  3  1  0
 13  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  8 21  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 14 28  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      48.302 -22.539   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      56.225 -19.594   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      53.761 -25.318   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      55.746 -21.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      54.239 -21.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.969 -23.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      49.636 -23.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.303 -24.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      53.761 -22.839   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      52.303 -23.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.659 -24.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.970 -22.539   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.636 -24.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      50.970 -25.619   0.000  0.00  0.00           C+0
CONECT    1    6    7                                                       
CONECT    2    4                                                            
CONECT    3    8   11                                                       
CONECT    4    2    5                                                       
CONECT    5    4    9                                                       
CONECT    6    1                                                            
CONECT    7    1   12   13                                                  
CONECT    8    3   10   14                                                  
CONECT    9    5   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    3    9                                                       
CONECT   12    7   10                                                       
CONECT   13    7   14                                                       
CONECT   14    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0004095
HETATM    1  C1  UNL     1      -2.814   2.341   0.417  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.215   1.035   0.733  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.340  -0.031   0.579  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.758  -1.318   0.898  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.881  -2.358   0.739  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.603  -2.141   0.270  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.451  -2.956   0.019  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.505  -2.259  -0.438  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.159  -0.928  -0.501  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.946   0.230  -0.930  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.449   1.086   0.189  1.00  0.00           C  
HETATM   12  N2  UNL     1       3.204   2.184  -0.356  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.158  -0.869  -0.057  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.060   0.174   0.111  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.074   2.696   1.178  1.00  0.00           H  
HETATM   16  H2  UNL     1      -2.302   2.351  -0.559  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.705   3.023   0.417  1.00  0.00           H  
HETATM   18  H4  UNL     1      -3.775  -1.426   1.263  1.00  0.00           H  
HETATM   19  H5  UNL     1      -2.201  -3.355   0.985  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.388  -3.986   0.182  1.00  0.00           H  
HETATM   21  H7  UNL     1       2.483  -2.657  -0.720  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.369   0.884  -1.616  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.842  -0.097  -1.532  1.00  0.00           H  
HETATM   24  H10 UNL     1       1.567   1.475   0.769  1.00  0.00           H  
HETATM   25  H11 UNL     1       3.087   0.567   0.917  1.00  0.00           H  
HETATM   26  H12 UNL     1       4.227   2.049  -0.337  1.00  0.00           H  
HETATM   27  H13 UNL     1       2.895   3.112  -0.041  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.687   1.173  -0.154  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4   14
CONECT    4    5   18
CONECT    5    6    6   19
CONECT    6    7   13
CONECT    7    8   20
CONECT    8    9    9   21
CONECT    9   10   13
CONECT   10   11   22   23
CONECT   11   12   24   25
CONECT   12   26   27
CONECT   13   14   14
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(5-Methoxyindol-3-yl)ethylamine	ChEBI
3-(2-Aminoethyl)-5-methoxyindole	ChEBI
5-MeOT	ChEBI
5-Methoxy-1H-indole-3-ethanamine	ChEBI
5-MT	ChEBI
5MOT	ChEBI
Mexamine	ChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanamine	HMDB
5-Mot	HMDB
Lopac-m-6628	HMDB
Meksamin	HMDB
Methoxytryptamine	HMDB
Mexamine base	HMDB
Meksamine	HMDB
5 Methoxytryptamine	HMDB
5-Methoxytryptamine	ChEBI

Chemical Formula

C₁₁H₁₄N₂O

Average Molecular Weight

190.2417

Monoisotopic Molecular Weight

190.11061308

IUPAC Name

2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Traditional Name

5 methoxytryptamine

CAS Registry Number

608-07-1

SMILES

COC1=CC2=C(NC=C2CCN)C=C1

InChI Identifier

InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

InChI Key

JTEJPPKMYBDEMY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
3-alkylindole
Indole
Anisole
2-arylethylamine
Alkyl aryl ether
Aralkylamine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:2089 )
tryptamines (CHEBI:2089 )
a small molecule (CPD-12018 )

Ontology

Not Available

Platelet (HMDB: HMDB0004095)

Organ

Gland

Thyroid gland (HMDB: HMDB0004095)
Thyroid gland (HMDB: HMDB0004095)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004095)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004095)

Source

Endogenous

Endogenous (HMDB: HMDB0004095)

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	141.182	30932474
[M-H]-	Not Available	141.182	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000359

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	1.41	ALOGPS
logP	1.33	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.45	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	51.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.84 m³·mol⁻¹	ChemAxon
Polarizability	21.32 Å³	ChemAxon
Number of Rings	2	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]+	141.8	31661259
DarkChem	[M-H]-	143.171	31661259
DeepCCS	[M+H]+	141.013	30932474
DeepCCS	[M-H]-	138.201	30932474
DeepCCS	[M-2H]-	174.132	30932474
DeepCCS	[M+Na]+	149.489	30932474
AllCCS	[M+H]+	142.6	32859911
AllCCS	[M+H-H2O]+	138.3	32859911
AllCCS	[M+NH4]+	146.6	32859911
AllCCS	[M+Na]+	147.7	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	146.1	32859911
AllCCS	[M+HCOO]-	146.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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. Predicted by Afia on May 17, 2022.	2.71 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9463 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.05 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	117.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	816.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	313.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	117.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	108.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	303.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	272.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	617.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	704.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	260.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	795.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	252.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	565.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	125.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptamine	COC1=CC2=C(NC=C2CCN)C=C1	2963.7	Standard polar	33892256
5-Methoxytryptamine	COC1=CC2=C(NC=C2CCN)C=C1	1987.9	Standard non polar	33892256
5-Methoxytryptamine	COC1=CC2=C(NC=C2CCN)C=C1	2045.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Methoxytryptamine,1TMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C)C2=C1	2089.1	Semi standard non polar	33892256
5-Methoxytryptamine,1TMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C)C2=C1	2183.0	Standard non polar	33892256
5-Methoxytryptamine,1TMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C)C2=C1	2684.6	Standard polar	33892256
5-Methoxytryptamine,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2038.7	Semi standard non polar	33892256
5-Methoxytryptamine,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2098.4	Standard non polar	33892256
5-Methoxytryptamine,1TMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C	2652.5	Standard polar	33892256
5-Methoxytryptamine,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C)=CN2[Si](C)(C)C	2141.6	Semi standard non polar	33892256
5-Methoxytryptamine,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C)=CN2[Si](C)(C)C	2241.4	Standard non polar	33892256
5-Methoxytryptamine,2TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C)=CN2[Si](C)(C)C	2437.9	Standard polar	33892256
5-Methoxytryptamine,2TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2276.6	Semi standard non polar	33892256
5-Methoxytryptamine,2TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2369.7	Standard non polar	33892256
5-Methoxytryptamine,2TMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C)[Si](C)(C)C)C2=C1	2582.0	Standard polar	33892256
5-Methoxytryptamine,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2361.1	Semi standard non polar	33892256
5-Methoxytryptamine,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2438.0	Standard non polar	33892256
5-Methoxytryptamine,3TMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C)[Si](C)(C)C)=CN2[Si](C)(C)C	2401.3	Standard polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C(C)(C)C)C2=C1	2382.1	Semi standard non polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C(C)(C)C)C2=C1	2371.7	Standard non polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #1	COC1=CC=C2[NH]C=C(CCN[Si](C)(C)C(C)(C)C)C2=C1	2742.5	Standard polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2280.9	Semi standard non polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2266.9	Standard non polar	33892256
5-Methoxytryptamine,1TBDMS,isomer #2	COC1=CC=C2C(=C1)C(CCN)=CN2[Si](C)(C)C(C)(C)C	2707.7	Standard polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2618.0	Semi standard non polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2628.5	Standard non polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2613.4	Standard polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	2733.4	Semi standard non polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	2747.1	Standard non polar	33892256
5-Methoxytryptamine,2TBDMS,isomer #2	COC1=CC=C2[NH]C=C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=C1	2696.8	Standard polar	33892256
5-Methoxytryptamine,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2985.7	Semi standard non polar	33892256
5-Methoxytryptamine,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2962.0	Standard non polar	33892256
5-Methoxytryptamine,3TBDMS,isomer #1	COC1=CC=C2C(=C1)C(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2673.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Platelet
Thyroid Gland

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0016 (0.0-0.0032) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	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

FDB023311

KNApSAcK ID

Not Available

Chemspider ID

1767

KEGG Compound ID

C05659

BioCyc ID

CPD-12018

BiGG ID

Not Available

Wikipedia Link

5-Methoxytryptamine

METLIN ID

7015

PubChem Compound

1833

PDB ID

Not Available

ChEBI ID

2089

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Szmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Geffard M, Dulluc J, Rock AM: Antisera against the indolealkylamines: tryptophan, 5-hydroxytryptophan, 5-hydroxytryptamine, 5-methoxytryptophan, and 5-methoxytryptamine tested by an enzyme-linked immunosorbent assay method. J Neurochem. 1985 Apr;44(4):1221-8. [PubMed:3919158 ]
Rom-Bugolavskaia ES, Shcherbakova VS, Komarova IV: [The effect of melatonin and mexamine on the human thyroid under in-vitro conditions]. Eksp Klin Farmakol. 1997 Jul-Aug;60(4):46-9. [PubMed:9376758 ]
Kirchheiner J, Henckel HB, Franke L, Meineke I, Tzvetkov M, Uebelhack R, Roots I, Brockmoller J: Impact of the CYP2D6 ultra-rapid metabolizer genotype on doxepin pharmacokinetics and serotonin in platelets. Pharmacogenet Genomics. 2005 Aug;15(8):579-87. [PubMed:16007002 ]
Romsing S, Bokman F, Bergqvist Y: Determination of melatonin in saliva using automated solid-phase extraction, high-performance liquid chromatography and fluorescence detection. Scand J Clin Lab Invest. 2006;66(3):181-90. [PubMed:16714247 ]

Enzymes

Enzyme Details

1. Serotonin N-acetyltransferase

General function:: Involved in N-acetyltransferase activity
Specific function:: Controls the night/day rhythm of melatonin production in the pineal gland. Catalyzes the N-acetylation of serotonin into N-acetylserotonin, the penultimate step in the synthesis of melatonin.
Gene Name:: AANAT
Uniprot ID:: Q16613
Molecular weight:: 23343.8

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

3. Protein arginine N-methyltransferase 3

General function:: Involved in protein methyltransferase activity
Specific function:: Methylates (mono and asymmetric dimethylation) the guanidino nitrogens of arginyl residues in some proteins
Gene Name:: PRMT3
Uniprot ID:: O60678
Molecular weight:: 59902.7

Enzyme Details

4. HemK methyltransferase family member 1

General function:: Not Available
Specific function:: N5-glutamine methyltransferase responsible for the methylation of the GGQ triplet of the mitochondrial translation release factor MTRF1L.
Gene Name:: HEMK1
Uniprot ID:: Q9Y5R4
Molecular weight:: Not Available

Reactions

Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic acid	details

Enzyme Details

5. Methyltransferase-like protein 2B

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL2B
Uniprot ID:: Q6P1Q9
Molecular weight:: Not Available

Reactions

Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic acid	details

Enzyme Details

6. Methyltransferase-like protein 6

General function:: Not Available
Specific function:: Probable methyltransferase (By similarity).
Gene Name:: METTL6
Uniprot ID:: Q8TCB7
Molecular weight:: Not Available

Reactions

Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic acid	details

Enzyme Details

7. Uncharacterized methyltransferase WBSCR22

General function:: Not Available
Specific function:: Methyltransferase that may act on DNA.
Gene Name:: WBSCR22
Uniprot ID:: O43709
Molecular weight:: Not Available

Reactions

Serotonin + 5-Methyltetrahydrofolic acid → 5-Methoxytryptamine + Tetrahydrofolic acid	details

Showing metabocard for 5-Methoxytryptamine (HMDB0004095)

MOL for HMDB0004095 (5-Methoxytryptamine)

3D MOL for HMDB0004095 (5-Methoxytryptamine)

3D SDF for HMDB0004095 (5-Methoxytryptamine)

3D-SDF for HMDB0004095 (5-Methoxytryptamine)

PDB for HMDB0004095 (5-Methoxytryptamine)

3D PDB for HMDB0004095 (5-Methoxytryptamine)

SMILES for HMDB0004095 (5-Methoxytryptamine)

INCHI for HMDB0004095 (5-Methoxytryptamine)

Structure for HMDB0004095 (5-Methoxytryptamine)

3D Structure for HMDB0004095 (5-Methoxytryptamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions