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

• ChemBase ID: 157726
• Molecular Formular: C16H27ClN2O3
• Molecular Mass: 330.85018
• Monoisotopic Mass: 330.17102041
• SMILES: CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC.Cl
• Canonical SMILES: CCCOc1ccc(cc1N)C(=O)OCCN(CC)CC.Cl
• InChI: InChI=1S/C16H26N2O3.ClH/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;1H
• InChIKey: BFUUJUGQJUTPAF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate hydrochloride
• IUPAC Traditional name: proparacaine hydrochloride; 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate hydrochloride
• Synonyms: Proparacaine hydrochloride; Alcaine; Opthaine; Proparacaine hydrochloride; Proxymetacaine Hydrochloride; 3-Amino-4-propoxybenzoic Acid 2-(Diethylamino)ethyl Ester Hydrochloride; 2-(Diethylamino)ethyl 3-Amino-4-propoxybenzoate Hydrochloride; Proxymetacaine Hydrochloride; Chibro-keracaine; Fluoracaine; Ophthain; Proparacaine Hydrochloride; Proparacaine HCl; 丙美卡因 盐酸盐

Database IDs

• CAS Number: 499-67-2; 5875-06-9
• EC Number: 227-541-7
• MDL Number: MFCD00083467
• PubChem SID: 162251863; 24898549
• PubChem CID: 517321

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.579591
• LogD (pH = 7.4): 1.0333513
• Log P: 2.6017163
• Molar Refractivity: 86.0358 cm^3
• Polarizability: 32.82243 Å^3
• Polar Surface Area: 64.79 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: White Solid
• Melting Point: 181-183°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: DG3065000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36-43
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H317-H319-H332
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Sodium Channel
• Mechanism of Action: 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.; The exact mechanism whereby proparacaine and other local anesthetics influence the permeability of the cell membrane is unknown; This limitation prevents the fundamental change necessary for the generation of the action potential.

Product Information

• Grade: analytical standard, for drug analysis
• Salt Data: HCl
• Application(s): Local anaesthetic (esp. ophthalmic)
• Empirical Formula (Hill Notation): C16H26N2O3 · HCl

DETAILS

Sigma Aldrich - P4554

Biochem/physiol Actions
Topical ophthalmic anesthetic

Toronto Research Chemicals - P761800

Topical anesthetic (ophthalmic).

REFERENCES

• McIntyre, S., et al.: J. Pharmacol. Exp. Ther., 63, 369 (1938)
• Whigan, D.B., et al.: Anal. Profiles Drug Subs., 6, 423 (1938)
• McIntyre, A.R. et al., J. Pharmacol. Exp. Ther., 1938, 63, 369, (pharmacol)
• Clinton, R.O. et al., J.A.C.S., 1952, 74, 592, (synth)
• Whigan, D.B., Anal. Profiles Drug Subst., 1977, 6, 423, (rev, synth, metab)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 4191
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1017