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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2017-12-07 01:46:50 UTC
HMDB IDHMDB0002004
Secondary Accession Numbers
  • HMDB02004
Metabolite Identification
Common 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 ).
Structure
Thumb
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
3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindoleHMDB
5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamineHMDB
5-Methoxy-N,N-dimethyltryptamineHMDB
5-Methoxyindole 3-(2-(N,N-dimethylamino)ethyl)HMDB
Bufotenine, 5-methoxydimethyltryptamineHMDB
MethylbufotenineHMDB
N,N-Dimethyl-5-methoxy tryptamineHMDB
MethoxydimethyltryptaminesMeSH
MethoxydimethyltryptamineMeSH
MethylbufoteninMeSH
5 Methoxy N,N dimethyltryptamineMeSH
N,N Dimethyl 5 methoxytryptamineMeSH
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
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
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
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
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.21 +/- 0.03 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.02 +/- 0.002 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.002 (0.00012-0.01) umol/mmol creatinineAdult (>18 years old)BothSurgical patients details
UrineDetected and Quantified0.0052 (0.0003-0.0094) umol/mmol creatinineAdult (>18 years old)BothPsychiatric disorder details
UrineDetected and Quantified0.00075 (0.00018-0.0027) umol/mmol creatinineAdult (>18 years old)BothInternal medical patients details
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 IDFDB022788
KNApSAcK IDNot Available
Chemspider ID1766
KEGG Compound IDC08309
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
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)Download (PDF)
General References
  1. Uebelhack R, Franke L, Seidel K: [Methylated and unmethylated indolamine in the cisternal fluid in acute endogenous psychoses]. Biomed Biochim Acta. 1983;42(10):1343-6. [PubMed:6144308 ]
  2. Forsstrom T, Tuominen J, Karkkainen J: Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Scand J Clin Lab Invest. 2001;61(7):547-56. [PubMed:11763413 ]