Record Information
Version1.0
Creation date2011-09-21 00:19:38 UTC
Update date2015-10-09 22:33:26 UTC
Primary IDFDB022788
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Methoxydimethyltryptamine
Description5-Methoxydimethyltryptamine, like all Methoxydimethyltryptamines is a compound that contain the biogenic monoamine tryptamine and is substituted with one methoxy group and two methyl groups. Members of this group include several potent serotonergic hallucinogens found in several unrelated plants, skins of certain toads, and in mammalian brains. They are possibly involved in the etiology of schizophrenia. (PubChem) They are formed as metabolites of serotonin (5-hydroxytryptamine) or tryptamine by the enzyme indolethylamine N-methyltransferase (INMT). The physiological significance of the N-methylating pathway of indoleamine metabolism, and of the methylated end products, is unknown. Because of the known psychotropic properties of the dimethylated amines, their possible involvement in the chemical pathogenesis of mental disorders has received wide interest. The hallucinogenic actions of the methylated indoleamines, like those of LSD, are believed to be mediated through the 5HT2 receptor. (PMID 11763413) [HMDB]
CAS Number1019-45-0
Structure
Thumb
Synonyms
SynonymSource
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
MethoxydimethyltryptaminesHMDB
MethoxydimethyltryptamineHMDB
MethylbufoteninHMDB
5 Methoxy N,N dimethyltryptamineHMDB
N,N Dimethyl 5 methoxytryptamineHMDB
3-[2-(N,N-dimethylamino)Ethyl]-5-methoxy-indoleChEBI
5-MeO-dmtChEBI
5-methoxy-N,N-dimethyl-1H-Indole-3-ethanaminehmdb
5-methoxyindole 3-(2-(N,N-Dimethylamino)ethyl)hmdb
Bufotenine, 5-Methoxydimethyltryptaminehmdb
O-methylbufoteninehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
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 RuleNoChemAxon
Chemical FormulaC13H18N2O
IUPAC name[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC2=C(NC=C2CCN(C)C)C=C1
Average Molecular Weight218.2948
Monoisotopic Molecular Weight218.141913208
Classification
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
Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Methoxydimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9310000000-095b611bc1d199502cb6Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05fr-5910000000-e732961434e6f6d047c6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-8900000000-1febcb75852e631248d3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a59-7900000000-dcdf4748d932c86ae91eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-60d541c0869cba86353fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-2a00c789bf0a52b49304Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-8e19cf440ade1a459473Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-5910000000-7d365fd4fa5aeedebef6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-8900000000-57e4ec6d746c4ef2bd66Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a59-7900000000-995a794ee19726d9dad1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-026ae917940e27f31556Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-05ai-2900000000-8e19cf440ade1a459473Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-df235ce53bdd863a3080Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-4950000000-458ffcc56b9f6180beb8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-3900000000-47db55905836c61c012eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-839bd41b21b5590a00e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-37decac3777ccc04b4c0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2900000000-635297b98da106f6c0e5Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID1766
ChEMBL IDCHEMBL7257
KEGG Compound IDC08309
Pubchem Compound ID1832
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02004
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference