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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:44 UTC
HMDB IDHMDB0014800
Secondary Accession Numbers
  • HMDB14800
Metabolite Identification
Common NameTrimethobenzamide
DescriptionTrimethobenzamide, also known as ametik damla or T-gen, 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. Trimethobenzamide is a drug which is used for the treatment of postoperative nausea and vomiting and for nausea associated with gastroenteritis. Based on a literature review a significant number of articles have been published on Trimethobenzamide.
Structure
Data?1582753222
Synonyms
ValueSource
N-[[4-(2-Dimethylaminoethoxy)phenyl]methyl]-3,4,5-trimethoxybenzamideChEBI
TrimethobenzamidumChEBI
TrimetobenzamidaChEBI
Ametik damlaKegg
T-GenHMDB
TebamideHMDB
TiganHMDB
Trimethobenzamide monohydrochlorideHMDB
TiconHMDB
Chemical FormulaC21H28N2O5
Average Molecular Weight388.4574
Monoisotopic Molecular Weight388.199822016
IUPAC NameN-({4-[2-(dimethylamino)ethoxy]phenyl}methyl)-3,4,5-trimethoxybenzamide
Traditional Nametrimethobenzamide
CAS Registry Number138-56-7
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 KeyFEZBIKUBAYAZIU-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentN-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.04 g/LNot Available
LogP2.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available193.34http://allccs.zhulab.cn/database/detail?ID=AllCCS00000724
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP2.44ALOGPS
logP2.16ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)14.36ChemAxon
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.26 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity108.52 m³·mol⁻¹ChemAxon
Polarizability43.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.59431661259
DarkChem[M-H]-191.99131661259
DeepCCS[M+H]+193.81330932474
DeepCCS[M-H]-191.45530932474
DeepCCS[M-2H]-225.61830932474
DeepCCS[M+Na]+200.84630932474
AllCCS[M+H]+195.832859911
AllCCS[M+H-H2O]+193.232859911
AllCCS[M+NH4]+198.132859911
AllCCS[M+Na]+198.832859911
AllCCS[M-H]-198.232859911
AllCCS[M+Na-2H]-198.832859911
AllCCS[M+HCOO]-199.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimethobenzamideCOC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C14033.7Standard polar33892256
TrimethobenzamideCOC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C13321.7Standard non polar33892256
TrimethobenzamideCOC1=CC(=CC(OC)=C1OC)C(=O)NCC1=CC=C(OCCN(C)C)C=C13330.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trimethobenzamide,1TMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC3096.8Semi standard non polar33892256
Trimethobenzamide,1TMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC3122.7Standard non polar33892256
Trimethobenzamide,1TMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C)=CC(OC)=C1OC3898.8Standard polar33892256
Trimethobenzamide,1TBDMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3351.2Semi standard non polar33892256
Trimethobenzamide,1TBDMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3274.0Standard non polar33892256
Trimethobenzamide,1TBDMS,isomer #1COC1=CC(C(=O)N(CC2=CC=C(OCCN(C)C)C=C2)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3954.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trimethobenzamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9503000000-470bcb74571cf77936cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimethobenzamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Positive-QTOFsplash10-000i-1509000000-a0aecd823447fda8b5812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Positive-QTOFsplash10-00fr-7903000000-371796a4982a6ca18e8d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Positive-QTOFsplash10-00fr-9600000000-3c0537fa07832854c2bd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Negative-QTOFsplash10-000i-0019000000-3f8b8afc43431a25c23f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Negative-QTOFsplash10-0i09-1239000000-8954d657acecb2570aec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Negative-QTOFsplash10-0h4o-6972000000-b5809e22e16fd9ec1ad72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Positive-QTOFsplash10-000i-1009000000-141c83bfee0ad68e6a872021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Positive-QTOFsplash10-00g0-5529000000-9b1cb5630b9473bf9bf42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Positive-QTOFsplash10-00di-9210000000-c806a75ff840adac07b52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 10V, Negative-QTOFsplash10-014r-0009000000-5c685906db39ec31b7922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 20V, Negative-QTOFsplash10-0uyr-1149000000-c28c4f592811edfc34182021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimethobenzamide 40V, Negative-QTOFsplash10-0udi-2239000000-657a89bdcdadde450f802021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00662 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00662 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00662
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5375
KEGG Compound IDC07178
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimethobenzamide
METLIN IDNot Available
PubChem Compound5577
PDB IDNot Available
ChEBI ID27796
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (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. [PubMed:5908416 ]
  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. [PubMed:7400373 ]