Tocainide (CED0010587)

Record Information

Version

1.0

Creation Date

2016-05-25 18:24:38 UTC

Update Date

2026-08-18 11:33:30 UTC

Accession Number

CHEM022225

Identification

Common Name

Tocainide

Class

Small Molecule

Description

Tocainide is an organic compound with the chemical formula C11H16N2O and an average molecular weight of 192.26 g/mol. Tocainide belongs to the xylenes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with seven recorded sources, including electrical and electronic equipment such as antennas, electric hearing aids, and electrically stimulated smoking devices. It is also found in household cleaning and consumer products, specifically cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. Additionally, it is utilized in healthcare, pharmaceuticals, and veterinary products as an antiarrhythmic of class I and III. The recorded route of exposure for this substance is oral. In terms of biological activity, tocainide acts as an inhibitor of the sodium channel protein type 5 subunit alpha (SCN5A), which is its single recorded protein target.

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-2',6'-propionoxylidide	ChEBI
2-Amino-N-(2,6-dimethylphenyl)propanamide	ChEBI
2-Amino-N-(2,6-dimethylphenyl)propionamid	ChEBI
Alanyl-2,6-xylidide	ChEBI
Tocainida	ChEBI
Tocainidum	ChEBI
AstraZeneca brand OF tocainide hydrochloride	HMDB
Tocainide hydrochloride	HMDB
Tocainide monohdyrochloride, (R)-isomer	HMDB
Tocainide monohydrobromide, (R)-isomer	HMDB
Tocainide monohydrochloride	HMDB
Tocainide, (+-)-isomer	HMDB
Tocainide, (R)-isomer	HMDB
Tocainide, (S)-isomer	HMDB
Tonocard	HMDB
Tocainide monohydrochloride, (+-)-isomer	HMDB
Tocainide monohydrochloride, (S)-isomer	HMDB
Xylotocan	HMDB
Hydrochloride, tocainide	HMDB

Chemical Formula

C₁₁H₁₆N₂O

Average Molecular Mass

192.258 g/mol

Monoisotopic Mass

192.126 g/mol

CAS Registry Number

41708-72-9

IUPAC Name

2-amino-N-(2,6-dimethylphenyl)propanamide

Traditional Name

tocainide

SMILES

CC(N)C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14)

InChI Key

BUJAGSGYPOAWEI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-Xylenes

Alternative Parents

Substituents

M-xylene
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:9611 )

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	1.6 g/L	ALOGPS
logP	0.55	ALOGPS
logP	1.88	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.12 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.86 m³·mol⁻¹	ChemAxon
Polarizability	21.59 Å³	ChemAxon
Number of Rings	1	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	splash10-006x-9700000000-90d7f8cfadbf5c481615	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0510000090-3faef8c50f47e62f2ac1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-0900000000-e3e09337d1b754b4c59c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0006-9400000000-578c55abffed08967f95	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-1900000000-c7d5dc77b594bd4bfb29	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-8900000000-54724c25ef578bc89366	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-9500000000-794c0ef462fb9d8c4369	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0900000000-700b3726d7cb4618c003	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-2900000000-4e4c7ecdb9ff631f04ea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00xr-3900000000-01c23922110972f5982f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-0900000000-32ecf76928a4f2d8612f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9800000000-6806af9483651aae91f1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9100000000-39dc3374e1a4d42414ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0900000000-4dd4451b1f851e3d0321	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-1900000000-6ddceb9e7f7ebd980bdd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-4900000000-2d6249a6af4ddf806fba	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
829.0	Log mg/kg	[470:1500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
285	Antiarrhythmics, class i and iii	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
556	Cigar Cigarettes	Household cleaning & consumer products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

5 pathways

Tocainide Action Pathway

Tocainide Sodium Channel Antiepileptic Action Pathway

Tocainide Sodium Channel Cardiac Muscle Relaxation Action Pathway

Tocainide Drug Metabolism Action Pathway

Tocainide Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Voltage-gated sodium channel Nav1.5 cardiac isoform	Q5YLN7	Canis lupus familiaris	Predicted (SEA)	8.40772
Click to view 3D structure	Solute carrier family 15 member 1	P46059	Humans	Predicted (SEA)	38.0683
Click to view 3D structure	Leucine--tRNA ligase	Q2FXH2	Staphylococcus aureus (strain NCTC 8325)	Predicted (SEA)	14.0907
Click to view 3D structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Predicted (SEA)	186.371
Click to view 3D structure	Cytosol aminopeptidase	P00727	Bos taurus	Predicted (SEA)	80.1847
Click to view 3D structure	Sphingosine 1-phosphate receptor 4	O95977	Humans	Predicted (SEA)	65.6269
Click to view 3D structure	D-alanyl-D-alanine carboxypeptidase	P39045	Actinomadura sp. (strain R39)	Predicted (SEA)	2.80257
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	276.598
Click to view 3D structure	Histone deacetylase 4	P56524	Humans	Predicted (SEA)	456.975
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	1240.61
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	2858.31
Click to view 3D structure	Kynureninase	P70712	Rattus norvegicus	Predicted (SEA)	9.10836
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	1098.53
Click to view 3D structure	Histone deacetylase 7	Q8WUI4	Humans	Predicted (SEA)	362.7
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	2262.61
Click to view 3D structure	Neprilysin	Q61391	Mus musculus	Predicted (SEA)	114.75
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	2333.37
Click to view 3D structure	Aminopeptidase N	P15145	Sus scrofa	Predicted (SEA)	167.999
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	254.022
Click to view 3D structure	Aminopeptidase B	Q8VCT3	Mus musculus	Predicted (SEA)	56.4407
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	767.749
Click to view 3D structure	Solute carrier family 15 member 2	Q16348	Humans	Predicted (SEA)	48.9672
Click to view 3D structure	Aminopeptidase N	P15144	Humans	Predicted (SEA)	245.147
Click to view 3D structure	Tyrosine-protein kinase JAK3	P52333	Humans	Predicted (SEA)	2207.8
Click to view 3D structure	Histone deacetylase 5	Q9UQL6	Humans	Predicted (SEA)	474.725