ContaminantDB: Trimethobenzamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:07 UTC

Update Date

2016-11-09 01:17:26 UTC

Accession Number

CHEM022156

Identification

Common Name

Trimethobenzamide

Class

Small Molecule

Description

The amide obtained by formal condensation of 3,4,5-trihydroxybenzoic acid with 4-[2-(N,N-dimethylamino)ethoxy]benzylamine. It is used to prevent nausea and vomitting in humans.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-[[4-(2-Dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamide	ChEBI
Trimethobenzamidum	ChEBI
Trimetobenzamida	ChEBI
Ametik damla	Kegg
T-Gen	HMDB
Tebamide	HMDB
Tigan	HMDB
Trimethobenzamide monohydrochloride	HMDB
Ticon	HMDB

Chemical Formula

C₂₁H₂₈N₂O₅

Average Molecular Mass

388.457 g/mol

Monoisotopic Mass

388.200 g/mol

CAS Registry Number

138-56-7

IUPAC Name

N-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide

Traditional Name

trimethobenzamide

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C1

InChI Identifier

InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24)

InChI Key

FEZBIKUBAYAZIU-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-benzylbenzamides. N-benzylbenzamides are compounds containing a benzamide moiety that is N-linked to a benzyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

N-benzylbenzamides

Alternative Parents

Substituents

N-benzylbenzamide
Anisole
Benzoyl
Phenol ether
Methoxybenzene
Phenoxy compound
Alkyl aryl ether
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:27796 )
benzamides (CHEBI:27796 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	2.44	ALOGPS
logP	2.16	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.26 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.52 m³·mol⁻¹	ChemAxon
Polarizability	43.19 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	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9503000000-470bcb74571cf77936cc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1509000000-a0aecd823447fda8b581	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00fr-7903000000-371796a4982a6ca18e8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fr-9600000000-3c0537fa07832854c2bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0019000000-3f8b8afc43431a25c23f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0i09-1239000000-8954d657acecb2570aec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0h4o-6972000000-b5809e22e16fd9ec1ad7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1009000000-141c83bfee0ad68e6a87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g0-5529000000-9b1cb5630b9473bf9bf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9210000000-c806a75ff840adac07b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0009000000-5c685906db39ec31b792	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uyr-1149000000-c28c4f592811edfc3418	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-2239000000-657a89bdcdadde450f80	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00662

HMDB ID

HMDB0014800

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Dundee JW, Halliday F, Nicholl RM, Moore J: Studies of drugs given before anaesthesia. X. Two non-phenothiazine anti-emetics--cyclizine and trimethobenzamide. Br J Anaesth. 1966 Jan;38(1):50-7.

2. Hurley JD, Eshelman FN: Trimethobenzamide HCl in the treatment of nausea and vomiting associated with antineoplastic chemotherapy. J Clin Pharmacol. 1980 May-Jun;20(5-6 Pt 1):352-6.

Trimethobenzamide (CHEM022156)

Structure for CHEM022156: Trimethobenzamide