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Human Metabolome Database Version 3.5

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Showing metabocard for 5-Methoxytryptamine (HMDB04095)

Record Information
Version 3.5
Creation Date 2006-08-13 04:47:12 -0600
Update Date 2013-02-08 17:13:00 -0700
HMDB ID HMDB04095
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Methoxytryptamine
Description Serotonin derivative proposed as potentiator for hypnotics and sedatives.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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 IUPAC 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
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Tryptamines 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 Parent Serotonins
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental 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
Predicted Properties
Property Value Source
Water Solubility 0.79 g/L ALOGPS
LogP 1.41 ALOGPS
LogP 1.33 ChemAxon
LogS -2.38 ALOGPS
pKa (strongest acidic) 17.45 ChemAxon
pKa (strongest basic) 9.76 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 51.04 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 56.84 ChemAxon
Polarizability 21.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location
  • Thyroid Gland
  • Platelet
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.0016 (0.0-0.0032) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023311
KNApSAcK ID Not Available
Chemspider ID 1767 Link_out
KEGG Compound ID C05659 Link_out
BioCyc ID N-ACETYL-5-METHOXY-TRYPTAMINE Link_out
BiGG ID Not Available
Wikipedia Link 5-Methoxytryptamine Link_out
NuGOwiki Link HMDB04095 Link_out
Metagene Link HMDB04095 Link_out
METLIN ID 7015 Link_out
PubChem Compound 1833 Link_out
PDB ID Not Available
ChEBI ID 2089 Link_out
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
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
Enzymes
Name: Serotonin N-acetyltransferase
Reactions:
  • acetyl-CoA + a 2-arylethylamine = CoA + an N-acetyl-2-arylethylamine [RN:R03760]
Gene Name: AANAT
Uniprot ID: Q16613 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amine oxidase [flavin-containing] A
Reactions:
  • RCH2NHR' + H2O + O2 = RCHO + R'NH2 + H2O2 [RN:R01853]
Gene Name: MAOA
Uniprot ID: P21397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein arginine N-methyltransferase 3
Reactions:
    Gene Name: PRMT3
    Uniprot ID: O60678 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA