Procaine (CED0002520)

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 an exogenous organic compound with the formula C13H20N2O2 and an average molecular weight of 236.31 g/mol. It exists as a solid at room temperature. Procaine belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This compound is used as a local anaesthetic, a peripheral nervous system drug, and a central nervous system depressant. Recorded exposure routes include intrathecal, subarachnoid, intraspinal, and infiltration. It is found in 13 recorded sources, including healthcare, pharmaceuticals and veterinary products (local anesthetics, anesthetics, and vasoprotectives), food preservation, household cleaning and consumer products (tobacco smoke filters, perfumes within detergents and soaps, and non electric simulated smoking devices), and electrical and electronic equipment (electrodes, radio transmission systems, television systems, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials). Procaine interacts with 21 recorded protein targets, including DNA (cytosine-5)-methyltransferase 1 (DNMT1), calcium-activated potassium channel subunit alpha-1 (KCNMA1), intermediate conductance calcium-activated potassium channel protein 4 (KCNN4), and a blocker/inhibitor effect on neuronal acetylcholine receptor subunit alpha-2 (CHRNA2). It also targets the 5-hydroxytryptamine receptor 3A (HTR3A), neuronal acetylcholine receptor subunit alpha-10 (CHRNA10), glutamate receptor ionotropic NMDA 3A (GRIN3A), and sodium channel protein type 10 subunit alpha (SCN10A). Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves, which prevents the arising of an action potential and inhibits signal conduction. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Additionally, procaine binds or antagonizes the function of nicotinic acetylcholine receptors, N-methyl-D-aspartate (NMDA) receptors, and the serotonin receptor-ion channel complex.

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

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	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	splash10-00dr-9400000000-a3ea7ca30e23e0b5e656	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0090000000-7c7d7173da9393c2d059	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0910000000-279febfbe258e2ce2807	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uk9-0900000000-997e743a0702a7a5b54f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2900000000-39c6b968e8d17c932e10	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00dl-9700000000-157dc94224e66c932ae8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-0900000000-050d794abd6d3a7e685d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01w0-1940000000-d4d5195f000d2d633df7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0290000000-3b9d79b65ba8cf449cf7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fe0-0950000000-b3df421e72e07cd2340b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-006x-9500000000-70455df4ef9797d6bd04	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1900000000-5270502b2011d8b676e6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0290000000-cfae604c83e71c8d9b48	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1900000000-1c49e394c0ac65a5b5e7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0h2r-0940000000-fa67a99b73e9f8654ad5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1900000000-8b6d76215bd17836c1a1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0290000000-e14a81a609614ad86d04	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-a05b40f792a408598bf8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-4900000000-e07128dfa197867a2d2a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0290000000-8cff9a94663a60aec4d4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0h2r-0940000000-41ba92f2d8bc9a66f635	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0fe0-0950000000-d1434b1f9db9f1ef3b37	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0290000000-773b582db316455919a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-5900000000-fbaaf06138cb0cfe5f17	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1900000000-232cd937791530cb2235	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fki-1690000000-87e7bf5ac9024bfe7cbb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uk9-3930000000-18dd034bea68e84f34de	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-006x-9200000000-983abfba088dd28ad16c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-3490000000-1d66ef09f6cac135ebfd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kr-8980000000-640e85b33add1758148c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00r6-9300000000-1c06ec2e51e41c54d063	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0590000000-4caa92a46cd547c5cec7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uk9-1910000000-4df7b8283c17d97d4f55	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dl-9800000000-9903cd2a5ca2b277cdb8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1390000000-fd63ccceb2d03b2eb1a1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-9770000000-ad6c395d4141d692dbd4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9000000000-d681b125b342a7a46f70	Not Available	View Spectrum
MS	MS Spectrum	splash10-000i-9200000000-44eb49be9b2baedfebdd	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

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.

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

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

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
350.0	mg/kg	Not Available	mouse	LD50	Oral	experimental	Not Available
1398.0	Log mg/kg	[790:2500]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
292	Vasoprotectives	Healthcare, pharmaceuticals & veterinary products	Not Available
369	Anesthetics	Healthcare, pharmaceuticals & veterinary products	Not Available
401	Local anesthetics	Healthcare, pharmaceuticals & veterinary products	Not Available
511	Conductors Or Conductive Bodies Characterised By The Conductive Materials	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
530	Radio Transmission Systems	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
561	Perfumes Within Detergents And Soaps	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
612	Body Washing Or Cleaning Implements	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
630	Toys	Recreation & sports surfaces	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available
662	Yarns Or Threads	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Procaine Pathway

Procaine Action Pathway

Procaine NMDA Antagonist Action Pathway

Procaine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	20.3965
Click to view 3D structure	Pancreatic alpha-amylase	P00689	Rattus norvegicus	Predicted (SEA)	0.389246
Click to view 3D structure	Muscarinic acetylcholine receptor M1	Q8WMX0	Bos taurus	Predicted (SEA)	2.25763
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	162.471
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	222.493
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	68.1181
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	4.43741
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	296.839
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	202.642
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	213.151
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	81.4303
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	300.342
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	254.178
Click to view 3D structure	Ubiquitin-conjugating enzyme E2 N	P61088	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	Acetylcholinesterase	P22303	Humans	Predicted (SEA)	282.048
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	319.182
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	333.039
Click to view 3D structure	Bcl-2-related protein A1	Q07440	Mus musculus	Predicted (SEA)	2.95827
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	1168.98
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	38.6911
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	8.01847
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	17.6718
Click to view 3D structure	Cyclic nucleotide-gated channel alpha-1	Q00194	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	32.3074
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	23.9776
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Known	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.
Click to view 3D structure	Glutamate receptor ionotropic, NMDA 3A	Q8TCU5	Humans	Known	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.
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-10	Q9GZZ6	Humans	Known	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.
Click to view 3D structure	Sodium channel protein type 10 subunit alpha	Q9Y5Y9	Humans	Known	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.
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Known	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.
Click to view 3D structure	Neuronal acetylcholine receptor subunit alpha-2	Q15822	Humans	Known	Not Available