ContaminantDB: Mepivacaine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:03 UTC

Update Date

2026-03-26 18:34:59 UTC

Accession Number

CHEM002313

Identification

Common Name

Mepivacaine

Class

Small Molecule

Description

A local anesthetic that is chemically related to bupivacaine but pharmacologically related to lidocaine. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168)

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amide
Amine
Anesthetic, Local
Drug
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1-Methyl-2',6'-pipecoloxylidide	ChEBI
1-Methyl-2',6'-pipecoloxylidide	ChEBI
Carbocaine	ChEBI
DL-Mepivacaine	ChEBI
Mepivacaina	ChEBI
Mepivacainum	ChEBI
N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide	ChEBI
N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide	ChEBI
Carboplyin dental	Kegg
Mepivacaine HCL	HMDB
Mepivacaine hydrochloride	HMDB
Mepivicaine	HMDB
S-Ropivacaine mesylate	HMDB
3m Brand OF mepivacaine hydrochloride	HMDB
AstraZeneca brand OF mepivacaine hydrochloride	HMDB
Inibsa brand OF mepivacaine hydrochloride	HMDB
Isogaine	HMDB
Mepivacain injektopas	HMDB
Mepivacaina braun	HMDB
Monohydrochloride, mepivacaine	HMDB
Pascoe brand OF mepivacaine hydrochloride	HMDB
Scandicaine	HMDB
Astra brand OF mepivacaine hydrochloride	HMDB
Hexal brand OF mepivacaine hydrochloride	HMDB
Hydrochloride, mepivacaine	HMDB
Mepihexal	HMDB
Mepivastesin	HMDB
Novocol brand OF mepivacaine hydrochloride	HMDB
Polocaine	HMDB
Curasan brand OF mepivacaine hydrochloride	HMDB
Abbott brand OF mepivacaine hydrochloride	HMDB
Braun, mepivacaina	HMDB
Clarben brand OF mepivacaine hydrochloride	HMDB
Dentsply brand OF mepivacaine hydrochloride	HMDB
Meaverin	HMDB
Mecain	HMDB
Sanofi brand OF mepivacaine hydrochloride	HMDB
Scandinibsa	HMDB
Aventis brand OF mepivacaine hydrochloride	HMDB
Braun brand OF mepivicaine hydrochloride	HMDB
Carbocaïne	HMDB
Isocaine	HMDB
Mepivacain-injektopas	HMDB
Mepivacaine monohydrochloride	HMDB
Scandicain	HMDB
Scandonest	HMDB

Chemical Formula

C₁₅H₂₂N₂O

Average Molecular Mass

246.348 g/mol

Monoisotopic Mass

246.173 g/mol

CAS Registry Number

96-88-8

IUPAC Name

N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide

Traditional Name

mepivacaine

SMILES

CN1CCCCC1C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

InChI Key

INWLQCZOYSRPNW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxamides

Alternative Parents

Substituents

2-piperidinecarboxamide
Piperidinecarboxamide
M-xylene
Xylene
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Carboximidic acid
Carboximidic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidinecarboxamide (CHEBI:6759 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Mepivacaine Pathway	Not Available	Not Available

Applications

local anaesthetic

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	150.5°C
Boiling Point	Not Available
Solubility	7000 mg/L (at 23°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	2.16	ALOGPS
logP	3.19	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	7.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.32 m³·mol⁻¹	ChemAxon
Polarizability	28.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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	splash10-0092-9200000000-a3a931af35da130669aa	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9040000000-3c0a89a13f39484eef97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-9073826aa2631981fe72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-9b273b91b5148ef6a8fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-d541d397ca20f2f1a799	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-eda45d03ea77058a8429	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-9000000000-f42a147676c3c718e38f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-9000000000-9073826aa2631981fe72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-9000000000-9b273b91b5148ef6a8fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-9040000000-3c0a89a13f39484eef97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-9000000000-d541d397ca20f2f1a799	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-9000000000-4b9a3b3048a6c1bbd656	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-006t-9000000000-f42a147676c3c718e38f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-e7a7508a46c81f01a0f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-2890000000-4fd4344949c8e98d2d22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006t-9600000000-eccb3e339a3aafb57c83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9100000000-923210fdcbf3093cec8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0190000000-5c29854d995646f8e15f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fs-0960000000-75e4d525847b240eb8dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0g4i-6900000000-79da7c9893bedd422f3e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9380000000-6935f06f321d22f49f8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9630000000-fc9251019b6aa4d95ac0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-64648fb1fd5128b76827	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-4a0996a0879be85733ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dj-0950000000-7a84cb81cb305d4c644e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xr-1910000000-dcbc91df93a09683c261	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-6a3d80d214452a24ab62	Spectrum

Toxicity Profile

Route of Exposure

Absorbed locally. The rate of systemic absorption of local anesthetics is dependent upon the total dose and concentration of drug administered, the route of administration, the vascularity of the administration site, and the presence or absence of epinephrine in the anesthetic solution. Subcutaneous, injection ; Infiltration

Mechanism of Toxicity

Local anesthetics block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. In general, the progression of anesthesia is related to the diameter, myelination, and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: pain, temperature, touch, proprioception, and skeletal muscle tone.

Metabolism

Rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine. The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Route of Elimination: It is rapidly metabolized, with only a small percentage of the anesthetic (5 percent to 10 percent) being excreted unchanged in the urine.The liver is the principal site of metabolism, with over 50% of the administered dose being excreted into the bile as metabolites. Half Life: The half-life of mepivacaine in adults is 1.9 to 3.2 hours and in neonates 8.7 to 9 hours.

Toxicity Values

The mean seizure dosage of mepivacaine in rhesus monkeys was found to be 18.8 mg/kg with mean arterial plasma concentration of 24.4 µg/mL. LD50: 23-35 mg/kg (Intravenous, Mouse) (1) LD50: 280 mg/kg (Subcutaneous, Mouse (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For production of local or regional analgesia and anesthesia by local infiltration, peripheral nerve block techniques, and central neural techniques including epidural and caudal blocks.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Treatment of a patient with toxic manifestations consists of assuring and maintaining a patient airway and supporting ventilation (respiration) as required. This usually will be sufficient in the management of most reactions. Should a convulsion persist despite ventilatory therapy, small increments of anticonvulsive agents may be given intravenously, such as benzodiazephine (e.g., diazepam) or ultrashort-acting barbiturates (e.g., thiopental or thiamylal) or short-acting barbiturates (e.g., pentobarbital or secobarbital). Cardiovascular depression may require circulatory assistance with intravenous fluids and/or vasopressor (e.g., Ephedrine) as dictated by the clinical situation. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB00961

HMDB ID

HMDB0015096

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID