5-Methoxytryptamine (CHEM021721)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:55 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021721
Identification
Common Name5-Methoxytryptamine
ClassSmall Molecule
Description5-Methoxytryptamine, also known as mexamine or 5-meot, 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. 5-Methoxytryptamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass190.242 g/mol
Monoisotopic Mass190.111 g/mol
CAS Registry Number608-07-1
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
Traditional Name5 methoxytryptamine
SMILESCOC1=CC2=C(NC=C2CCN)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ue9-1960000000-9d22140ff2b48f31db09Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00dr-3900000000-b121de7d00a382123401Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ue9-1960000000-9d22140ff2b48f31db09Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00dr-3900000000-b121de7d00a382123401Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dr-2900000000-a5fe7e3acae8eed474deSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-2900000000-2b80fe48b74acca6bebfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-c9d325a89238b38270a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00dr-0900000000-ac5e7141a1f9a408fc34Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0900000000-6e5b3b429a1bb70ffaf4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-0900000000-e60ae04a11b9e498a966Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-54e5a7201f25456dcad8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-1900000000-293475115ff46b97099aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-1900000000-a14a529194c5227e34f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-002f-0900000000-ad73b33b853950cd5689Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-54e5a7201f25456dcad8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1900000000-adf7f816d92642625bddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-66f8cb9c260ecf410ce1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-a14a529194c5227e34f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002f-0900000000-ad73b33b853950cd5689Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-485d7582e65bfa3e31f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-db26f9e0d37f5c251c53Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-eaf537b355550eb27e55Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-478e855c47b694b99c9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-3096f67fc0f5797d14b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-2d015296f43e86be7b7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-2a2466c60f7faa96dccaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-0900000000-c4f465460bde21d469beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-0900000000-f1d40ff7aa6c88ecdfd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-05fr-0900000000-22d3b9e8cbdb136bcb64Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-0900000000-74e1867f5b88bc53f677Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-001i-0900000000-438c89f58ad3c0098959Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004095
FooDB IDFDB023311
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12018
METLIN ID7015
PDB IDNot Available
Wikipedia Link5-Methoxytryptamine
Chemspider ID1767
ChEBI ID2089
PubChem Compound ID1833
Kegg Compound IDC05659
YMDB IDNot Available
ECMDB IDM2MDB004613
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Szmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9.
2. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1.
3. Szmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9.
4. 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.
5. 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.
6. 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.
7. 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.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22678752
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23451999