Showing Compound 5-Methoxydimethyltryptamine (FDB022788)

Record Information

Version

1.0

Creation date

2011-09-21 00:19:38 UTC

Update date

2015-10-09 22:33:26 UTC

Primary ID

FDB022788

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-Methoxydimethyltryptamine

Description

5-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 Number

1019-45-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindole	HMDB
3-(2-Dimethylaminoethyl)-5-methoxyindole	ChEBI
3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indole	ChEBI
3-[2-(N,N-dimethylamino)Ethyl]-5-methoxy-indole	ChEBI
5 Methoxy N,N dimethyltryptamine	MeSH, HMDB
5-MeO-DMT	ChEBI
5-MeO-dmt	ChEBI
5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine	ChEBI
5-methoxy-N,N-dimethyl-1H-Indole-3-ethanamine	hmdb
5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamine	HMDB

Showing 1 to 10 of 26 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.14	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	17.44	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.91 m³·mol⁻¹	ChemAxon
Polarizability	25.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C13H18N2O

IUPAC name

[2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine

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 Key

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(NC=C2CCN(C)C)C=C1

Average Molecular Weight

218.2948

Monoisotopic Molecular Weight

218.141913208

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:2086 )
aromatic ether (CHEBI:2086 )
tryptamine alkaloid (CHEBI:2086 )
Indole alkaloids (C08309 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	5-Methoxydimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9310000000-095b611bc1d199502cb6	Spectrum
Predicted GC-MS	5-Methoxydimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	5-Methoxydimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0090000000-81cb5c66bea4c4f559a7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-05fr-5910000000-e732961434e6f6d047c6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0ab9-8900000000-4a1b4b925b663d3894ef	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a4i-8900000000-1febcb75852e631248d3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a59-7900000000-dcdf4748d932c86ae91e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-60d541c0869cba86353f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a4i-0900000000-2a00c789bf0a52b49304	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-05ai-2900000000-8e19cf440ade1a459473	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0090000000-81cb5c66bea4c4f559a7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-05fr-5910000000-7d365fd4fa5aeedebef6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0ab9-8900000000-4a1b4b925b663d3894ef	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a4i-8900000000-57e4ec6d746c4ef2bd66	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a59-7900000000-995a794ee19726d9dad1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-00di-0900000000-026ae917940e27f31556	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-05ai-2900000000-8e19cf440ade1a459473	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0390000000-df235ce53bdd863a3080	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0600-4950000000-458ffcc56b9f6180beb8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-3900000000-47db55905836c61c012e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-839bd41b21b5590a00e9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0190000000-37decac3777ccc04b4c0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-2900000000-635297b98da106f6c0e5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-09dd32e79c2ea83c7941	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0290000000-05df1c62ff8d5cce80bd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-0900000000-37c7f3dd2cc5915c3750	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0190000000-3c41a600694ff73dfe05	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02004

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 5-Methoxydimethyltryptamine (FDB022788)

Structure for FDB022788 (5-Methoxydimethyltryptamine)