2-(diethylamino)ethyl 4-aminobenzoate

• ChemBase ID: 602
• Molecular Formular: C13H20N2O2
• Molecular Mass: 236.3101
• Monoisotopic Mass: 236.15247789
• SMILES: O(CCN(CC)CC)C(=O)c1ccc(N)cc1
• Canonical SMILES: CCN(CCOC(=O)c1ccc(cc1)N)CC
• InChI: 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
• InChIKey: MFDFERRIHVXMIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)ethyl 4-aminobenzoate
• IUPAC Traditional name: procaine
• Brand Name: Allocaine; Chloroprocaine Hcl; Diethylaminoethyl P-Aminobenzoate; Duracaine; Duracillin A.S.; Gerovital; Gerovital H-3; Jenacain; Jenacaine; Neocaine; Nesacaine; Nissocaine; Norocaine; Novocain; Novocaine; P-Aminobenzoyldiethylaminoethanol; Penicillin G Procaine; Pfizerpen-As; Procain; Procaine Hcl; Procaine Hydrochloride; Procaine, Base; Scurocaine; Spinocaine; Vitamin H3; Anticort
• Synonyms: procaine HCl; Procaine; 4-Aminobenzoic acid 2-diethylaminoethyl ester; 2-(Diethylamino)ethyl-4-aminobenzoate; 4-Aminobenzoic acid 2-(diethylamino) ethyl ester; p-Aminobenzyoyldiethylaminoethanol; 2-Diethylaminoethyl p-aminobenzoate; Duracaine; Gerovital; Vitamin H3

Database IDs

• CAS Number: 59-46-1
• EC Number: 200-426-9
• MDL Number: MFCD00007893
• PubChem SID: 160964065; 46507724
• PubChem CID: 4914

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.3007611
• LogD (pH = 7.4): 0.31169838
• Log P: 1.8800572
• Molar Refractivity: 70.3 cm^3
• Polarizability: 26.619965 Å^3
• Polar Surface Area: 55.56 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.1
• LOG S: -1.54
• Solubility (Water): 6.81e+00 g/l

PROPERTIES

Physical Property

• Solubility: 9450 mg/L
• Melting Point: 61 °C
• Hydrophobicity(logP): 1.8

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: IRRITANT
• RTECS: DG2100000
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: false

Product Information

• Purity: 95%; 95+%

DETAILS

MP Biomedicals - 02190263

Free Base
Crystalline

DrugBank - DB00721

• Drug Groups: approved; investigational
• Description: 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]
• Indication: Used as a local anesthetic primarily in oral surgery
• Pharmacology: Procaine is an anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Procaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine. Procaine is an ester anesthetic. It is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-aminobenzoic acid (PABA), which is then excreted by the kidneys into the urine.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hydrolysis by plasma esterases to PABA
• Half Life: 7.7 minutes
• Elimination: With normal kidney function, the drug is excreted rapidly by tubular excretion.
• References: Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. J Pharmacol Exp Ther. 2001 Dec;299(3):1038-48. [Pubmed]
• External Links: Wikipedia; Drugs.com

Apollo Scientific Ltd - OR4842

Base USP

REFERENCES

• Gentry CL, Lukas RJ: Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. J Pharmacol Exp Ther. 2001 Dec;299(3):1038-48. Pubmed