ContaminantDB: Procaine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (26)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:29 UTC

Update Date

2026-05-14 16:47:04 UTC

Accession Number

CHEM002257

Identification

Common Name

Procaine

Class

Small Molecule

Description

Procaine is only found in individuals that have used or taken this drug. It is a local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016). [PubChem]Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Anesthetic
Anesthetic, Local
Drug
Ester
Ether
Food Toxin
Human Neurotoxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Diethylaminoethyl p-aminobenzoate	ChEBI
4-Aminobenzoic acid 2-diethylaminoethyl ester	ChEBI
beta-(Diethylamino)ethyl 4-aminobenzoate	ChEBI
beta-(Diethylamino)ethyl p-aminobenzoate	ChEBI
Novocaine	ChEBI
p-Aminobenzoic acid 2-diethylaminoethyl ester	ChEBI
Procaina	ChEBI
Procainum	ChEBI
Vitamin H3	ChEBI
Solution OF novocain	Kegg
2-Diethylaminoethyl p-aminobenzoic acid	Generator
4-Aminobenzoate 2-diethylaminoethyl ester	Generator
b-(Diethylamino)ethyl 4-aminobenzoate	Generator
b-(Diethylamino)ethyl 4-aminobenzoic acid	Generator
beta-(Diethylamino)ethyl 4-aminobenzoic acid	Generator
Β-(diethylamino)ethyl 4-aminobenzoate	Generator
Β-(diethylamino)ethyl 4-aminobenzoic acid	Generator
b-(Diethylamino)ethyl p-aminobenzoate	Generator
b-(Diethylamino)ethyl p-aminobenzoic acid	Generator
beta-(Diethylamino)ethyl p-aminobenzoic acid	Generator
Β-(diethylamino)ethyl p-aminobenzoate	Generator
Β-(diethylamino)ethyl p-aminobenzoic acid	Generator
p-Aminobenzoate 2-diethylaminoethyl ester	Generator
Procaine HCL	HMDB
Chaix et du marais brand OF procaine hydrochloride	HMDB
Geriocaine	HMDB
Hewedolor-procain	HMDB
Procain jenapharm	HMDB
Procain rödler	HMDB
Procain steigerwald	HMDB
Röwo procain	HMDB
Abbott brand OF procaine hydrochloride	HMDB
Aventis brand OF procaine hydrochloride	HMDB
Hevert brand OF procaine hydrochloride	HMDB
Hydrochloride, procaine	HMDB
Jenapharm brand OF procaine hydrochloride	HMDB
Procain curasan	HMDB
Serra pamies brand OF procaine hydrochloride	HMDB
Steigerwald brand OF procaine hydrochloride	HMDB
Anuject	HMDB
Gerokit	HMDB
Lophakomp-procain N	HMDB
Procaina serra	HMDB
Procaine hydrochloride	HMDB
Pröcaine chlorhydrate lavoisier	HMDB
Curasan brand OF procaine hydrochloride	HMDB
Procain-loges	HMDB
Braun brand OF procaine hydrochloride	HMDB
Loges brand OF procaine hydrochloride	HMDB
Lomapharm brand OF procaine hydrochloride	HMDB
Novocain	HMDB
Pharmakon brand OF procaine hydrochloride	HMDB
Procain braun	HMDB

Chemical Formula

C₁₃H₂₀N₂O₂

Average Molecular Mass

236.310 g/mol

Monoisotopic Mass

236.152 g/mol

CAS Registry Number

59-46-1

IUPAC Name

2-(diethylamino)ethyl 4-aminobenzoate

Traditional Name

procaine

SMILES

CCN(CC)CCOC(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3

InChI Key

MFDFERRIHVXMIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Aminobenzoic acid or derivatives
Benzoate ester
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8430 )
substituted aniline (CHEBI:8430 )
benzoate ester (CHEBI:8430 )

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
Procaine Pathway	Not Available	Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	61°C
Boiling Point	Not Available
Solubility	9450 mg/L (at 30°C)

Predicted Properties

Property	Value	Source
Water Solubility	6.81 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.88	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	70.3 m³·mol⁻¹	ChemAxon
Polarizability	26.81 Å³	ChemAxon
Number of Rings	1	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	splash10-00dr-9400000000-a3ea7ca30e23e0b5e656	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-QQ , positive	splash10-000i-0090000000-7c7d7173da9393c2d059	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0910000000-279febfbe258e2ce2807	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0uk9-0900000000-997e743a0702a7a5b54f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00di-2900000000-39c6b968e8d17c932e10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00dl-9700000000-157dc94224e66c932ae8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0w29-0900000000-050d794abd6d3a7e685d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01w0-1940000000-d4d5195f000d2d633df7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0290000000-3b9d79b65ba8cf449cf7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0fe0-0950000000-b3df421e72e07cd2340b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-006x-9500000000-70455df4ef9797d6bd04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-1900000000-5270502b2011d8b676e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0290000000-cfae604c83e71c8d9b48	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-1900000000-1c49e394c0ac65a5b5e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0h2r-0940000000-fa67a99b73e9f8654ad5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-00di-1900000000-8b6d76215bd17836c1a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0290000000-e14a81a609614ad86d04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0900000000-a05b40f792a408598bf8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00di-4900000000-e07128dfa197867a2d2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0290000000-8cff9a94663a60aec4d4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fki-1690000000-87e7bf5ac9024bfe7cbb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-3930000000-18dd034bea68e84f34de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9200000000-983abfba088dd28ad16c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3490000000-1d66ef09f6cac135ebfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-8980000000-640e85b33add1758148c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r6-9300000000-1c06ec2e51e41c54d063	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9200000000-44eb49be9b2baedfebdd	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, Infiltration, Intramuscular

Mechanism of Toxicity

Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.

Metabolism

Hydrolysis by plasma esterases to PABA Route of Elimination: With normal kidney function, the drug is excreted rapidly by tubular excretion. Half Life: 7.7 minutes

Toxicity Values

LD50: 350 mg/kg (Oral, mouse).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

It is used primarily to reduce the pain of intramuscular injection of penicillin, and it is also used in dentistry. [Wikipedia]

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

An allergic reaction (difficulty breathing; closing of the throat; swelling of the lips, tongue, or face; or hives); chest pain or slow or irregular heartbeats; dizziness or drowsiness; anxiety or restlessness; nausea or vomiting; trembling, shaking, or seizures (convulsions). Other less serious side effects such as numbness, tingling, or minor pain at or around the injection site are more likely to occur.(3)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00721

HMDB ID

HMDB0014859

FooDB ID

FDB029371

Phenol Explorer ID