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Record Information
Version3.6
Creation Date2006-08-13 10:47:12 UTC
Update Date2013-02-09 00:13:00 UTC
HMDB IDHMDB04095
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Methoxytryptamine
DescriptionSerotonin derivative proposed as potentiator for hypnotics and sedatives.
Structure
Thumb
Synonyms
  1. 2-(5-Methoxy-1H-indol-3-yl)ethanamine
  2. 2-(5-Methoxyindol-3-yl)ethylamine
  3. 3-(2-Aminoethyl)-5-methoxyindole
  4. 5-Mot
  5. 5MOT
  6. Lopac-M-6628
  7. Meksamin
  8. Methoxytryptamine
  9. Mexamine
  10. Mexamine base
Chemical FormulaC11H14N2O
Average Molecular Weight190.2417
Monoisotopic Molecular Weight190.11061308
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
Traditional Name5-methoxytryptamine
CAS Registry Number608-07-1
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 KeyJTEJPPKMYBDEMY-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassIndoles
Sub ClassTryptamines and Derivatives
Other Descriptors
  • Indoles
  • Tryptamines and Derivatives
  • a small molecule(Cyc)
  • tryptamines(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrole
Direct ParentSerotonins
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point121.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.79 g/LALOGPS
logP1.41ALOGPS
logP1.33ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)17.45ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area51.04ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.84ChemAxon
Polarizability21.32ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue Location
  • Platelet
  • Thyroid Gland
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0016 (0.0-0.0032) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023311
KNApSAcK IDNot Available
Chemspider ID1767
KEGG Compound IDC05659
BioCyc IDN-ACETYL-5-METHOXY-TRYPTAMINE
BiGG IDNot Available
Wikipedia Link5-Methoxytryptamine
NuGOwiki LinkHMDB04095
Metagene LinkHMDB04095
METLIN ID7015
PubChem Compound1833
PDB IDNot Available
ChEBI ID2089
References
Synthesis ReferenceSzmuszkovicz, 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
  1. 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
  2. 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
  3. 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
  4. 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

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
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
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
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 aciddetails
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 aciddetails
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 aciddetails
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 aciddetails