Trimethobenzamide (CED0013569)

Record Information

Version

1.0

Creation Date

2016-05-25 18:22:07 UTC

Update Date

2026-08-21 19:44:00 UTC

SynCED ID

CED0013569

Secondary Accession Numbers

CHEM022156

Identification

Common Name

Trimethobenzamide

Class

Small Molecule

Description

Trimethobenzamide is an organic compound with the chemical formula C21H28N2O5 and an average molecular weight of 388.46 g/mol. Trimethobenzamide belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is classified within the superclass of benzenoids. Regarding its biological activity, trimethobenzamide acts as an inhibitor of the D(2) dopamine receptor (DRD2). The compound is found in or released from eight recorded sources, including healthcare, pharmaceuticals, and veterinary products where it is used as an antihistamine. It is also associated with household cleaning and consumer products, specifically tobacco smoke filters, cigar cigarettes, other smoking requisites, and non-electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, such as antennas, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded routes of exposure for this compound include oral, rectal, and intramuscular administration.

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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-9503000000-470bcb74571cf77936cc	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1509000000-a0aecd823447fda8b581	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-7903000000-371796a4982a6ca18e8d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-9600000000-3c0537fa07832854c2bd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0019000000-3f8b8afc43431a25c23f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0i09-1239000000-8954d657acecb2570aec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h4o-6972000000-b5809e22e16fd9ec1ad7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1009000000-141c83bfee0ad68e6a87	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00g0-5529000000-9b1cb5630b9473bf9bf4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9210000000-c806a75ff840adac07b5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014r-0009000000-5c685906db39ec31b792	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uyr-1149000000-c28c4f592811edfc3418	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2239000000-657a89bdcdadde450f80	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1115.0 Log mg/kg [630:2000]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000393	Antihistamines?Antihistamines are a class of synthetic chemicals primarily used to alleviate allergic reactions by blocking the action of histamine in the body.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000678	Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.	Agriculture & land management	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000688	Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000739	Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.	Paper, pulp & fiber products	PubChem

Pathways

1 pathwayPathway Source: PathBank

Trimethobenzamide Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.431 Statistical Significance 0.0358 Supporting Reference Compounds 1538 E-value 278.467
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.431 Statistical Significance 0.0223 Supporting Reference Compounds 834 E-value 173.682
Click to view 3D structure	Rho-associated protein kinase 2	O75116	Humans	Predicted (SEA)	Prediction Confidence Score 0.369 Applicability Domain 0.431 Statistical Significance 0.0249 Supporting Reference Compounds 811 E-value 193.922
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.368 Applicability Domain 0.415 Statistical Significance 0.027 Supporting Reference Compounds 955 E-value 210.037
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	Prediction Confidence Score 0.354 Applicability Domain 0.388 Statistical Significance 0.0198 Supporting Reference Compounds 553 E-value 154.219
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	Prediction Confidence Score 0.346 Applicability Domain 0.388 Statistical Significance 0.0249 Supporting Reference Compounds 497 E-value 193.689
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	Prediction Confidence Score 0.341 Applicability Domain 0.366 Statistical Significance 0.0068 Supporting Reference Compounds 201 E-value 52.9375
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	Prediction Confidence Score 0.338 Applicability Domain 0.388 Statistical Significance 0.0672 Supporting Reference Compounds 1301 E-value 523.302
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.336 Applicability Domain 0.431 Statistical Significance 0.0452 Supporting Reference Compounds 1130 E-value 351.878
Click to view 3D structure	Equilibrative nucleoside transporter 2	O54699	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 0.333 Statistical Significance 6.90e-04 Supporting Reference Compounds 1 E-value 5.3716
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.362 Statistical Significance 0.0742 Supporting Reference Compounds 1130 E-value 577.563
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.327 Applicability Domain 0.368 Statistical Significance 0.0483 Supporting Reference Compounds 527 E-value 376.167
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.325 Applicability Domain 0.368 Statistical Significance 0.0397 Supporting Reference Compounds 562 E-value 309.451
Click to view 3D structure	Sodium- and chloride-dependent glycine transporter 2	Q9Y345	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.415 Statistical Significance 1.60e-04 Supporting Reference Compounds 15 E-value 1.24559
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.362 Statistical Significance 0.0141 Supporting Reference Compounds 373 E-value 109.845
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.322 Applicability Domain 0.349 Statistical Significance 0.081 Supporting Reference Compounds 1157 E-value 630.423
Click to view 3D structure	Vascular endothelial growth factor receptor 1	P17948	Humans	Predicted (SEA)	Prediction Confidence Score 0.322 Applicability Domain 0.349 Statistical Significance 0.0567 Supporting Reference Compounds 711 E-value 441.561
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.322 Applicability Domain 0.356 Statistical Significance 0.018 Supporting Reference Compounds 365 E-value 140.129
Click to view 3D structure	Inward rectifier potassium channel 2	P35561	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.321 Applicability Domain 0.321 Statistical Significance 0.0015 Supporting Reference Compounds 1 E-value 11.6774
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.32 Applicability Domain 0.362 Statistical Significance 0.0255 Supporting Reference Compounds 487 E-value 198.282
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.319 Applicability Domain 0.362 Statistical Significance 0.0607 Supporting Reference Compounds 707 E-value 472.311
Click to view 3D structure	5-hydroxytryptamine receptor 1B	P28222	Humans	Predicted (SEA)	Prediction Confidence Score 0.317 Applicability Domain 0.356 Statistical Significance 0.0197 Supporting Reference Compounds 337 E-value 153.052
Click to view 3D structure	Estrogen-related receptor gamma	P62508	Humans	Predicted (SEA)	Prediction Confidence Score 0.316 Applicability Domain 0.362 Statistical Significance 7.20e-04 Supporting Reference Compounds 18 E-value 5.60514
Click to view 3D structure	Aurora kinase A	O14965	Humans	Predicted (SEA)	Prediction Confidence Score 0.315 Applicability Domain 0.349 Statistical Significance 0.083 Supporting Reference Compounds 996 E-value 646.46
Click to view 3D structure	Histone deacetylase 2	Q92769	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.388 Statistical Significance 0.0278 Supporting Reference Compounds 307 E-value 216.343