Milk Composition Database: Showing metabocard for 5-Methoxytryptamine (BMDB0004095)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:07:54 UTC

Update Date

2020-05-11 22:30:23 UTC

MCDB ID

BMDB0004095

Secondary Accession Numbers

BMDB04095

Metabolite Identification

Common Name

5-Methoxytryptamine

Description

5-Methoxytryptamine, also known as mexamine or 5-meot, 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. 5-Methoxytryptamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 5-Methoxytryptamine exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(5-Methoxyindol-3-yl)ethylamine	ChEBI
3-(2-Aminoethyl)-5-methoxyindole	ChEBI
5-MeOT	ChEBI
5-Methoxy-1H-indole-3-ethanamine	ChEBI
5-MT	ChEBI
5MOT	ChEBI
Mexamine	ChEBI
2-(5-Methoxy-1H-indol-3-yl)ethanamine	HMDB
5-Mot	HMDB
Lopac-m-6628	HMDB
Meksamin	HMDB
Methoxytryptamine	HMDB
Mexamine base	HMDB
Meksamine	HMDB
5 Methoxytryptamine	HMDB
5-Methoxytryptamine	ChEBI

Chemical Formula

C₁₁H₁₄N₂O

Average Molecular Weight

190.2417

Monoisotopic Molecular Weight

190.11061308

IUPAC Name

2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Traditional Name

5 methoxytryptamine

CAS Registry Number

608-07-1

SMILES

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

InChI Identifier

InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3

InChI Key

JTEJPPKMYBDEMY-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.

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
Anisole
2-arylethylamine
Alkyl aryl ether
Aralkylamine
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Ether
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:2089 )
tryptamines (CHEBI:2089 )
a small molecule (CPD-12018 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	121.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.41	ALOGPS
logP	1.33	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.45	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	51.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.84 m³·mol⁻¹	ChemAxon
Polarizability	21.32 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0ue9-1960000000-9d22140ff2b48f31db09	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00dr-3900000000-b121de7d00a382123401	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0ue9-1960000000-9d22140ff2b48f31db09	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dr-3900000000-b121de7d00a382123401	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dr-2900000000-a5fe7e3acae8eed474de	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-2900000000-2b80fe48b74acca6bebf	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6900000000-c9d325a89238b38270a6	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00dr-0900000000-ac5e7141a1f9a408fc34	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-0900000000-6e5b3b429a1bb70ffaf4	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-0900000000-e60ae04a11b9e498a966	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-54e5a7201f25456dcad8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-1900000000-293475115ff46b97099a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0006-1900000000-66f8cb9c260ecf410ce1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-1900000000-a14a529194c5227e34f8	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-002f-0900000000-ad73b33b853950cd5689	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-54e5a7201f25456dcad8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-1900000000-adf7f816d92642625bdd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-66f8cb9c260ecf410ce1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-a14a529194c5227e34f8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-002f-0900000000-ad73b33b853950cd5689	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-485d7582e65bfa3e31f1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-db26f9e0d37f5c251c53	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-eaf537b355550eb27e55	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-478e855c47b694b99c9c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-3096f67fc0f5797d14b7	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-2d015296f43e86be7b7e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0900000000-2a2466c60f7faa96dcca	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00di-0900000000-c4f465460bde21d469be	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-0900000000-f1d40ff7aa6c88ecdfd5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-05fr-0900000000-22d3b9e8cbdb136bcb64	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-0900000000-74e1867f5b88bc53f677	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-001i-0900000000-438c89f58ad3c0098959	2012-08-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 29197344	details

External Links

HMDB ID

HMDB0004095

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023311

KNApSAcK ID

Not Available

Chemspider ID

1767

KEGG Compound ID

C05659

BioCyc ID

CPD-12018

BiGG ID

Not Available

Wikipedia Link

5-Methoxytryptamine

METLIN ID

7015

PubChem Compound

1833

PDB ID

Not Available

ChEBI ID

2089

References

Synthesis Reference

Szmuszkovicz, J.; Anthony, W. C.; Heinzelman, R. V. N-Acetyl-5-methoxytryptamine. Journal of Organic Chemistry (1960), 25 857-9.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]

Showing metabocard for 5-Methoxytryptamine (BMDB0004095)

Structure for BMDB0004095 (5-Methoxytryptamine)