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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 10:47:12 UTC
Update Date2017-10-23 19:04:10 UTC
HMDB IDHMDB0004095
Secondary Accession Numbers
  • HMDB04095
Metabolite Identification
Common Name5-Methoxytryptamine
DescriptionSerotonin derivative proposed as potentiator for hypnotics and sedatives.
Structure
Thumb
Synonyms
ValueSource
2-(5-Methoxyindol-3-yl)ethylamineChEBI
3-(2-Aminoethyl)-5-methoxyindoleChEBI
5-MeOTChEBI
5-Methoxy-1H-indole-3-ethanamineChEBI
5-MTChEBI
5MOTChEBI
MexamineChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanamineHMDB
5-MotHMDB
Lopac-m-6628HMDB
MeksaminHMDB
MethoxytryptamineHMDB
Mexamine baseHMDB
MeksamineMeSH
5 MethoxytryptamineMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

  Organ and components:

    Endocrine gland:

  Cell and elements:

    Element:

Source:

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 Area51.04 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.84 m³·mol⁻¹ChemAxon
Polarizability21.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ue9-1960000000-9d22140ff2b48f31db09View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-3900000000-b121de7d00a382123401View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-1960000000-9d22140ff2b48f31db09View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-3900000000-b121de7d00a382123401View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-a5fe7e3acae8eed474deView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-2b80fe48b74acca6bebfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-c9d325a89238b38270a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dr-0900000000-ac5e7141a1f9a408fc34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0900000000-6e5b3b429a1bb70ffaf4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-0900000000-e60ae04a11b9e498a966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-54e5a7201f25456dcad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-1900000000-293475115ff46b97099aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-a14a529194c5227e34f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-002f-0900000000-ad73b33b853950cd5689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-c4f465460bde21d469beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-f1d40ff7aa6c88ecdfd5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-0900000000-22d3b9e8cbdb136bcb64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-0900000000-74e1867f5b88bc53f677View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-438c89f58ad3c0098959View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-54e5a7201f25456dcad8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-adf7f816d92642625bddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-a14a529194c5227e34f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-0900000000-ad73b33b853950cd5689View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-485d7582e65bfa3e31f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-f95e78148902f5d5fd5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-df05e0b6cdfd7405bd61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-29075396a509857c49cfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-d54a34cc910e2e660e8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-7444dab440e6fbc176f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-e4e316fc6ae64a01da7fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue Location
  • Platelet
  • Thyroid Gland
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDCPD-12018
BiGG IDNot Available
Wikipedia Link5-Methoxytryptamine
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