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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 10:47:12 UTC
Update Date2021-09-07 16:45:36 UTC
HMDB IDHMDB0004095
Secondary Accession Numbers
  • HMDB04095
Metabolite Identification
Common Name5-Methoxytryptamine
Description5-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
Data?1582752298
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
MeksamineHMDB
5 MethoxytryptamineHMDB
5-MethoxytryptamineChEBI
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
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.
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

Source:

Biological location:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ue9-1960000000-9d22140ff2b48f31db092014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-3900000000-b121de7d00a3821234012014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-1960000000-9d22140ff2b48f31db092017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-3900000000-b121de7d00a3821234012017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-a5fe7e3acae8eed474de2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-2b80fe48b74acca6bebf2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-c9d325a89238b38270a62017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-6900000000-c9d325a89238b38270a62021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dr-0900000000-ac5e7141a1f9a408fc342012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0900000000-6e5b3b429a1bb70ffaf42012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-0900000000-e60ae04a11b9e498a9662012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-54e5a7201f25456dcad82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-1900000000-293475115ff46b97099a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-1900000000-66f8cb9c260ecf410ce12012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-a14a529194c5227e34f82012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-002f-0900000000-ad73b33b853950cd56892012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-c4f465460bde21d469be2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-f1d40ff7aa6c88ecdfd52012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-0900000000-22d3b9e8cbdb136bcb642012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-0900000000-74e1867f5b88bc53f6772012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-438c89f58ad3c00989592012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-54e5a7201f25456dcad82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-adf7f816d92642625bdd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-66f8cb9c260ecf410ce12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-a14a529194c5227e34f82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-0900000000-ad73b33b853950cd56892017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-485d7582e65bfa3e31f12017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0900000000-f95e78148902f5d5fd5c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-df05e0b6cdfd7405bd612017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-29075396a509857c49cf2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-d54a34cc910e2e660e8f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-7444dab440e6fbc176f12017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-e4e316fc6ae64a01da7f2017-09-01View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue Locations
  • Platelet
  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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. 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 ]
  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 ]
  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 ]
  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 ]

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