5-Methoxydimethyltryptamine (CHEM021771)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:12:07 UTC
Update Date2016-11-09 01:17:21 UTC
Accession NumberCHEM021771
Identification
Common Name5-Methoxydimethyltryptamine
ClassSmall Molecule
DescriptionA tryptamine alkaloid that is N,N-dimethyltryptamine substituted by a methoxy group at position 5.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass218.295 g/mol
Monoisotopic Mass218.142 g/mol
CAS Registry Number1019-45-0
IUPAC Name[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
Traditional Name5-MeO-DMT
SMILESCOC1=CC2=C(NC=C2CCN(C)C)C=C1
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
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
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 Solubility0.72 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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9310000000-095b611bc1d199502cb6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-05fr-5910000000-e732961434e6f6d047c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-8900000000-1febcb75852e631248d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a59-7900000000-dcdf4748d932c86ae91eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-60d541c0869cba86353fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-2a00c789bf0a52b49304Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05ai-2900000000-8e19cf440ade1a459473Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0090000000-81cb5c66bea4c4f559a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05fr-5910000000-7d365fd4fa5aeedebef6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ab9-8900000000-4a1b4b925b663d3894efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-8900000000-57e4ec6d746c4ef2bd66Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a59-7900000000-995a794ee19726d9dad1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-026ae917940e27f31556Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05ai-2900000000-8e19cf440ade1a459473Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0390000000-df235ce53bdd863a3080Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0600-4950000000-458ffcc56b9f6180beb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-3900000000-47db55905836c61c012eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-839bd41b21b5590a00e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0190000000-37decac3777ccc04b4c0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-2900000000-635297b98da106f6c0e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-09dd32e79c2ea83c7941Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0290000000-05df1c62ff8d5cce80bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-0900000000-37c7f3dd2cc5915c3750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0190000000-3c41a600694ff73dfe05Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
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 IDHMDB0002004
FooDB IDFDB022788
Phenol Explorer IDNot Available
KNApSAcK IDC00001420
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link5-MeO-DMT
Chemspider ID1766
ChEBI ID2086
PubChem Compound ID1832
Kegg Compound IDC08309
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11763413
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19490926
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24650558
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25446678
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26477571
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=28993683
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=29708042
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=30233313
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=30471678
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=30574112
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=30822141
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=30982127
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=31019450
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=31822925
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=31923390
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=32148190
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=33851996
18. Bertaccini, Giulio; Vitali, Tullo. Synthesis and pharmacological activity of some 5- methoxyindole derivatives occurring in nature. Farmaco, Edizione Scientifica (1967), 22(4), 229-44.
19. 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.
20. 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.