N-(2-methylphenyl)-2-(propylamino)propanamide

• ChemBase ID: 630
• Molecular Formular: C13H20N2O
• Molecular Mass: 220.3107
• Monoisotopic Mass: 220.15756327
• SMILES: O=C(Nc1c(cccc1)C)C(NCCC)C
• Canonical SMILES: CCCNC(C(=O)Nc1ccccc1C)C
• InChI: InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
• InChIKey: MVFGUOIZUNYYSO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-methylphenyl)-2-(propylamino)propanamide
• IUPAC Traditional name: prilocaine
• Brand Name: Astra 1512; Astra 1515; Citanest; Citanest Plain; Propitocaine
• Synonyms: Prilocaine; N-[2-Methylphenyl]-2-[propylamino]propanamide; PRILOCAINE HYDROCHLORIDE

Database IDs

• CAS Number: 1786-81-8; 721-50-6
• EC Number: 217-244-0
• PubChem SID: 46505066; 160964093
• PubChem CID: 4906

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.509082
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.29579815
• LogD (pH = 7.4): 1.2547785
• Log P: 2.6809227
• Molar Refractivity: 67.863 cm^3
• Polarizability: 25.874826 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -2.83
• Solubility (Water): 3.26e-01 g/l

PROPERTIES

Physical Property

• Solubility: 541 mg/L
• Melting Point: 167-168°C
• Hydrophobicity(logP): 2.1

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: UG5775000

Product Information

• Salt Data: Free Base

DETAILS

MP Biomedicals - 02156365

Hydrochloride

DrugBank - DB00750

• Drug Groups: approved
• Description: A local anesthetic that is similar pharmacologically to lidocaine. Currently, it is used most often for infiltration anesthesia in dentistry. (From AMA Drug Evaluations Annual, 1992, p165)
• Indication: Used as a local anaesthetic and is often used in dentistry.
• Pharmacology: Prilocaine binds to the intracellular surface of sodium channels which blocks the subsequent influx of sodium into the cell. Action potential propagation and never function is, therefore, prevented. This block is reversible and when the drug diffuses away from the cell, sodium channel function is restored and nerve propagation returns.
• Affected Organisms: Humans and other mammals
• Protein Binding: 98%
• Elimination: Prilocaine is metabolized in both the liver and the kidney and excreted via the kidney.
• External Links: Wikipedia

Selleck Chemicals - S1619

Research Area: Neurological Disease
Biological Activity:
Prilocaine is a local anesthetic of the amino amide type. It is often used in dentistry. It is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia. As it has low cardiac toxicity, it is commonly used for intravenous regional anaesthesia (IVRA). [1]

REFERENCES

• http://en.wikipedia.org/wiki/Prilocaine