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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:31 UTC
Update Date2021-09-07 16:45:32 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. 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
Data?1582752222
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg153.75930932474
[M+H]+MetCCS_train_pos151.52230932474
[M-H]-Not Available153.759http://allccs.zhulab.cn/database/detail?ID=AllCCS00000351
[M+H]+Not Available151.702http://allccs.zhulab.cn/database/detail?ID=AllCCS00000351
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.9531661259
DarkChem[M-H]-149.62831661259
DeepCCS[M+H]+152.2330932474
DeepCCS[M-H]-149.87230932474
DeepCCS[M-2H]-183.56530932474
DeepCCS[M+Na]+158.48730932474
AllCCS[M+H]+149.732859911
AllCCS[M+H-H2O]+145.732859911
AllCCS[M+NH4]+153.432859911
AllCCS[M+Na]+154.432859911
AllCCS[M-H]-156.132859911
AllCCS[M+Na-2H]-156.332859911
AllCCS[M+HCOO]-156.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-MethoxydimethyltryptamineCOC1=CC2=C(NC=C2CCN(C)C)C=C12882.5Standard polar33892256
5-MethoxydimethyltryptamineCOC1=CC2=C(NC=C2CCN(C)C)C=C11981.7Standard non polar33892256
5-MethoxydimethyltryptamineCOC1=CC2=C(NC=C2CCN(C)C)C=C11988.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Methoxydimethyltryptamine,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C2034.5Semi standard non polar33892256
5-Methoxydimethyltryptamine,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C2102.8Standard non polar33892256
5-Methoxydimethyltryptamine,1TMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C2389.2Standard polar33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C2234.7Semi standard non polar33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C2307.8Standard non polar33892256
5-Methoxydimethyltryptamine,1TBDMS,isomer #1COC1=CC=C2C(=C1)C(CCN(C)C)=CN2[Si](C)(C)C(C)(C)C2499.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxydimethyltryptamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-095b611bc1d199502cb62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxydimethyltryptamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Methoxydimethyltryptamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-014i-0090000000-81cb5c66bea4c4f559a72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-05fr-5910000000-e732961434e6f6d047c62012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0ab9-8900000000-4a1b4b925b663d3894ef2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-0a4i-8900000000-1febcb75852e631248d32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-0a59-7900000000-dcdf4748d932c86ae91e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-00di-0900000000-60d541c0869cba86353f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOFsplash10-0a4i-0900000000-2a00c789bf0a52b493042012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-qTof , Positive-QTOFsplash10-05ai-2900000000-8e19cf440ade1a4594732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOFsplash10-014i-0090000000-81cb5c66bea4c4f559a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOFsplash10-05fr-5910000000-7d365fd4fa5aeedebef62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOFsplash10-0ab9-8900000000-4a1b4b925b663d3894ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOFsplash10-0a4i-8900000000-57e4ec6d746c4ef2bd662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-QQ , positive-QTOFsplash10-0a59-7900000000-995a794ee19726d9dad12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine LC-ESI-IT , positive-QTOFsplash10-00di-0900000000-026ae917940e27f315562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Methoxydimethyltryptamine , positive-QTOFsplash10-05ai-2900000000-8e19cf440ade1a4594732017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Positive-QTOFsplash10-014i-0390000000-df235ce53bdd863a30802017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Positive-QTOFsplash10-0600-4950000000-458ffcc56b9f6180beb82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Positive-QTOFsplash10-0aou-3900000000-47db55905836c61c012e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Negative-QTOFsplash10-014i-0090000000-839bd41b21b5590a00e92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Negative-QTOFsplash10-014i-0190000000-37decac3777ccc04b4c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Negative-QTOFsplash10-052f-2900000000-635297b98da106f6c0e52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Negative-QTOFsplash10-014i-0090000000-09dd32e79c2ea83c79412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 20V, Negative-QTOFsplash10-014i-0290000000-05df1c62ff8d5cce80bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 40V, Negative-QTOFsplash10-0a4l-0900000000-37c7f3dd2cc5915c37502021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Methoxydimethyltryptamine 10V, Positive-QTOFsplash10-014i-0190000000-3c41a600694ff73dfe052021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 References
Major depressive disorder
  1. 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 ]
Associated OMIM IDs
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]