Showing metabocard for 5-Methoxydimethyltryptamine (BMDB0002004)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:47 UTC
Update Date2020-04-22 15:09:20 UTC
BMDB IDBMDB0002004
Secondary Accession Numbers
  • BMDB02004
Metabolite Identification
Common Name5-Methoxydimethyltryptamine
Description5-Methoxydimethyltryptamine, also known as methoxybufotenin or 5-meo-DMT, 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. Based on a literature review a significant number of articles have been published on 5-Methoxydimethyltryptamine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(2-Dimethylaminoethyl)-5-methoxyindoleChEBI
3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indoleChEBI
5-MeO-DMTChEBI
5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamineChEBI
MeODMTChEBI
MethoxybufoteninChEBI
N,N-Dimethyl-5-methoxytryptamineChEBI
O-MethylbufotenineChEBI
5-Methoxy-N,N-dimethyltryptamineKegg
3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindoleHMDB
5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamineHMDB
5-Methoxyindole 3-(2-(N,N-dimethylamino)ethyl)HMDB
Bufotenine, 5-methoxydimethyltryptamineHMDB
MethylbufotenineHMDB
N,N-Dimethyl-5-methoxy tryptamineHMDB
MethoxydimethyltryptaminesMeSH, HMDB
MethoxydimethyltryptamineMeSH, HMDB
MethylbufoteninMeSH, HMDB
5 Methoxy N,N dimethyltryptamineMeSH, HMDB
N,N Dimethyl 5 methoxytryptamineMeSH, HMDB
Chemical FormulaC13H18N2O
Average Molecular Weight218.2948
Monoisotopic Molecular Weight218.141913208
IUPAC Name[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
Traditional Name5-MeO-DMT
CAS Registry Number1019-45-0
SMILES
COC1=CC2=C(NC=C2CCN(C)C)C=C1
InChI Identifier
InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
InChI KeyZSTKHSQDNIGFLM-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
  • Alkaloid or derivatives
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Ether
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)17.44ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.26 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.91 m³·mol⁻¹ChemAxon
Polarizability25.47 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-095b611bc1d199502cb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05fr-5910000000-e732961434e6f6d047c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-8900000000-1febcb75852e631248d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a59-7900000000-dcdf4748d932c86ae91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-60d541c0869cba86353fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-2a00c789bf0a52b49304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-8e19cf440ade1a459473View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-5910000000-7d365fd4fa5aeedebef6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-8900000000-57e4ec6d746c4ef2bd66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a59-7900000000-995a794ee19726d9dad1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-026ae917940e27f31556View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05ai-2900000000-8e19cf440ade1a459473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-df235ce53bdd863a3080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-4950000000-458ffcc56b9f6180beb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-3900000000-47db55905836c61c012eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-839bd41b21b5590a00e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-37decac3777ccc04b4c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2900000000-635297b98da106f6c0e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-09dd32e79c2ea83c7941View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0290000000-05df1c62ff8d5cce80bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0900000000-37c7f3dd2cc5915c3750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-3c41a600694ff73dfe05View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002004
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022788
KNApSAcK IDC00001420
Chemspider ID1766
KEGG Compound IDC08309
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-MeO-DMT
METLIN IDNot Available
PubChem Compound1832
PDB IDNot Available
ChEBI ID2086
References
Synthesis ReferenceBertaccini, Giulio; Vitali, Tullo. Synthesis and pharmacological activity of some 5- methoxyindole derivatives occurring in nature. Farmaco, Edizione Scientifica (1967), 22(4), 229-44.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available