Proparacaine (CED0003678)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:41 UTC

Update Date

2026-05-14 16:49:29 UTC

SynCED ID

CED0003678

Secondary Accession Numbers

CHEM002276
T3D2896

Identification

Common Name

Proparacaine

Class

Small Molecule

Description

Proparacaine is an exogenous compound with the formula C16H26N2O3 and an average molecular weight of 294.39 g/mol. It exists as a solid at room temperature. Proparacaine belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. This compound is recorded as a local anesthetic and is found in several sources, including healthcare, pharmaceuticals, and veterinary products. Other recorded sources include household cleaning and consumer products such as perfumes within detergents and soaps, tobacco smoke filters, and cigar cigarettes, as well as electrical and electronic equipment such as electrically stimulated smoking devices and conductive bodies characterized by conductive materials. The recorded exposure route is ophthalmic. Proparacaine has two recorded protein targets: transient receptor potential cation channel subfamily A member 1 (TRPA1) and sodium channel protein type 10 subunit alpha (SCN10A). Regarding the latter, proparacaine may alter epithelial sodium channels through interaction with channel protein residues. While the exact mechanism by which local anesthetics influence cell membrane permeability is unknown, several studies indicate they may limit sodium ion permeability through the lipid layer of the nerve cell membrane, which prevents the fundamental change necessary for the generation of the action potential.

Contaminant Type

Amine
Anesthetic, Local
Drug
Ester
Ether
Lachrymator
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Proxymetacaine	Kegg
Prossimetacaina	HMDB
Proximetacainum	HMDB
Ophthetic	HMDB
Parcaine	HMDB
Alcaine	HMDB
Ocu-caine	HMDB
Proxymetacaine hydrochloride	HMDB
AK-taine	HMDB
Kainair	HMDB
Proxymethacaine	HMDB
Chibro-kerakain	HMDB
Kéracaine	HMDB
Minims proxymetacaine hydrochloride	HMDB
Ophthaine	HMDB
Proparakain-pos	HMDB
Proxymetacaine monohydrochloride	HMDB
Proparacaine hydrochloride	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester	HMDB
2-(Diethylamino)ethyl 3-amino-4-propoxybenzoate monohydrochloride	HMDB
Benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride*benzoic acid, 3-amino-4-propoxy-, 2-(diethylamino)ethyl ester, monohydrochloride	HMDB
Proparacaine HCL	HMDB

Chemical Formula

C₁₆H₂₆N₂O₃

Average Molecular Mass

294.389 g/mol

Monoisotopic Mass

294.194 g/mol

CAS Registry Number

499-67-2

IUPAC Name

2-(diethylamino)ethyl 3-amino-4-propoxybenzoate

Traditional Name

proparacaine

SMILES

CCCOC1=C(N)C=C(C=C1)C(=O)OCCN(CC)CC

InChI Identifier

InChI=1S/C16H26N2O3/c1-4-10-20-15-8-7-13(12-14(15)17)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3

InChI Key

KCLANYCVBBTKTO-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
Aminophenyl ether
Phenoxy compound
Benzoyl
Aniline or substituted anilines
Phenol ether
Alkyl aryl ether
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:8485 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

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

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	182-183.3°C
Boiling Point	Not Available
Solubility	1.39e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	1.39 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.6	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.79 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.04 m³·mol⁻¹	ChemAxon
Polarizability	34 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	splash10-000i-9320000000-1725fcdf405f1285cf5f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f6t-0590000000-0aae7080739b3c83b4a4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f92-3790000000-19484885f2060a30ee39	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-6940000000-b6eb0be7d6e42c79f6d2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9300000000-8b40ab2bb2e6ca190ac6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-2490000000-e0dd5d94666e639cd15f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udl-3890000000-83f45f2c670646cf13b4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-4910000000-080bada57e1dc3ab313c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0940000000-dd6bde08618373162607	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2950000000-6cf937b31cea35f9327a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-2900000000-74d2433c695036dfb8f5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-0490000000-6934514b2f05a7f1e043	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udj-2930000000-d9841e3d4745b761afc5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zg0-0900000000-acfb0c0e342bd2f577c8	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
1242.0 Log mg/kg [700:2200]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Dizziness or drowsiness; increased sweating; irregular heartbeat; muscle twitching or trembling; nausea or vomiting; shortness of breath or troubled breathing; unusual excitement, nervousness, or restlessness; unusual tiredness or weakness. Burning, stinging, redness, or other irritation of eye. (1)

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000401	Local anesthetics?Local anesthetics are synthetic chemical compounds used to induce a reversible loss of sensation in specific areas of the body.	Healthcare, pharmaceuticals & veterinary products	Not Available
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
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
CEDs000561	Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.	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
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000603	Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.	Agriculture & land management	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	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
CEDs000614	Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	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
CEDs000674	Bridle Bits?Bridle bits, commonly used in equestrian activities, can be a source of synthetic chemical contamination primarily through the materials used in their manufacturing.	Agriculture & land management	PubChem
CEDs000677	Horse Reins?Horse reins, often made from synthetic materials such as nylon or polyester, can be a source of chemical contamination due to their production and degradation processes.	Agriculture & land management	PubChem
CEDs000679	Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.	Agriculture & land management	PubChem
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	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
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Proparacaine Pathway

Proparacaine Action Pathway

Proparacaine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.488 Applicability Domain 1.0 Statistical Significance 0.003 Supporting Reference Compounds 562 E-value 23.3548
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	Prediction Confidence Score 0.409 Applicability Domain 1.0 Statistical Significance 0.0028 Supporting Reference Compounds 241 E-value 21.4864
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.352 Applicability Domain 0.377 Statistical Significance 0.0021 Supporting Reference Compounds 98 E-value 16.1148
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	Prediction Confidence Score 0.349 Applicability Domain 0.377 Statistical Significance 0.0075 Supporting Reference Compounds 373 E-value 58.3091
Click to view 3D structure	Cyclic nucleotide-gated channel alpha-1	Q00194	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.336 Applicability Domain 0.375 Statistical Significance 6.00e-05 Supporting Reference Compounds 2 E-value 0.467095
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	Prediction Confidence Score 0.334 Applicability Domain 0.377 Statistical Significance 0.0124 Supporting Reference Compounds 385 E-value 96.6109
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.377 Statistical Significance 0.0088 Supporting Reference Compounds 310 E-value 68.7409
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	Prediction Confidence Score 0.332 Applicability Domain 0.377 Statistical Significance 0.0085 Supporting Reference Compounds 297 E-value 65.9383
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.375 Statistical Significance 0.0371 Supporting Reference Compounds 823 E-value 288.743
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.375 Statistical Significance 0.0479 Supporting Reference Compounds 955 E-value 372.82
Click to view 3D structure	Pancreatic alpha-amylase	P00689	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.377 Statistical Significance 1.60e-04 Supporting Reference Compounds 2 E-value 1.24559
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	Prediction Confidence Score 0.314 Applicability Domain 0.333 Statistical Significance 0.0538 Supporting Reference Compounds 861 E-value 418.517
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.312 Applicability Domain 0.333 Statistical Significance 0.0405 Supporting Reference Compounds 686 E-value 314.978
Click to view 3D structure	Muscarinic acetylcholine receptor M1	Q8WMX0	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.311 Applicability Domain 0.377 Statistical Significance 6.40e-04 Supporting Reference Compounds 18 E-value 4.98235
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.3 Applicability Domain 0.333 Statistical Significance 0.0413 Supporting Reference Compounds 487 E-value 321.829
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	Prediction Confidence Score 0.3 Applicability Domain 0.333 Statistical Significance 0.0453 Supporting Reference Compounds 536 E-value 352.501
Click to view 3D structure	Ubiquitin-conjugating enzyme E2 N	P61088	Humans	Predicted (SEA)	Prediction Confidence Score 0.297 Applicability Domain 0.364 Statistical Significance 1.50e-04 Supporting Reference Compounds 46 E-value 1.16774
Click to view 3D structure	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Q15125	Humans	Predicted (SEA)	Prediction Confidence Score 0.296 Applicability Domain 0.333 Statistical Significance 0.002 Supporting Reference Compounds 27 E-value 15.4141
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.296 Applicability Domain 0.351 Statistical Significance 0.0583 Supporting Reference Compounds 528 E-value 454.017
Click to view 3D structure	Apoptotic protease-activating factor 1	O14727	Humans	Predicted (SEA)	Prediction Confidence Score 0.294 Applicability Domain 0.364 Statistical Significance 0.0023 Supporting Reference Compounds 112 E-value 17.5939
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	Prediction Confidence Score 0.292 Applicability Domain 0.333 Statistical Significance 0.0242 Supporting Reference Compounds 266 E-value 188.473
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	Prediction Confidence Score 0.288 Applicability Domain 0.333 Statistical Significance 0.1189 Supporting Reference Compounds 707 E-value 925.627
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.288 Applicability Domain 0.328 Statistical Significance 0.1171 Supporting Reference Compounds 1103 E-value 911.692
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.287 Applicability Domain 0.333 Statistical Significance 0.1584 Supporting Reference Compounds 1130 E-value 1232.98
Click to view 3D structure	UDP-3-O-acyl-N-acetylglucosamine deacetylase	O67648	Aquifex aeolicus (strain VF5)	Predicted (SEA)	Prediction Confidence Score 0.283 Applicability Domain 0.283 Low confidence Statistical Significance 0.0067 Supporting Reference Compounds 1 E-value 52.0033
Click to view 3D structure	Sodium channel protein type 10 subunit alpha	Q9Y5Y9	Humans	Known	The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; however, several studies indicate that local anesthetics may limit sodium ion permeability through the lipid layer of the nerve cell membrane. Proparacaine may alter epithelial sodium channels through interaction with channel protein residues. This limitation prevents the fundamental change necessary for the generation of the action potential.
Click to view 3D structure	Transient receptor potential cation channel subfamily A member 1	O75762	Humans	Known	Not Available