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

• ChemBase ID: 130781
• Molecular Formular: C13H21ClN2O
• Molecular Mass: 256.77164
• Monoisotopic Mass: 256.13424098
• SMILES: CCCNC(C)C(=O)Nc1ccccc1C.Cl
• Canonical SMILES: CCCNC(C(=O)Nc1ccccc1C)C.Cl
• InChI: InChI=1S/C13H20N2O.ClH/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);1H
• InChIKey: BJPJNTKRKALCPP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-methylphenyl)-2-(propylamino)propanamide hydrochloride
• IUPAC Traditional name: prilocaine hydrochloride
• Synonyms: N-(3-Methylphenyl)-2-(propylamino)propanamide Hydrochloride; 2-(Propylamino)-m-propionotoluidide Hydrochloride; N-(2-Methylphenyl)-2-(propylamino)propanamide Hydrochloride; 2-(Propylamino)-o-propionotoluidide Hydrochloride; Citanest Hydrochloride; L 67; L 67 Hydrochloride; Prilocaine Chloride; Xylonest; Prilocaine Hydrochloride; Prilocaine hydrochloride; N-(2-甲基苯基)-2-丙胺-丙酰胺 盐酸盐; 丙胺卡因 盐酸盐

Database IDs

• CAS Number: 878791-35-6; 1786-81-8
• EC Number: 217-244-0
• MDL Number: MFCD00079279
• PubChem SID: 162225059; 24898404; 24278664
• PubChem CID: 92163

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: UG5775000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC)
• Suitability: meets USP testing specifications

DETAILS

Sigma Aldrich - P9547

Biochem/physiol Actions
Used for local nerve block and for spinal anesthesia; pharmacological properties are similar to those of lidocaine.

Toronto Research Chemicals - P834500

A substituted toluidide for use as local anaesthetics.

Toronto Research Chemicals - P725000

Prilocaine is a local anesthetic of the amino amide type. Prilocaine is often used in dentistry. Prilocaine is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like pares

REFERENCES

• Nussbaum, M., et al.: J. Pharm. Biomed. Anal., 27, 983 (2002)
• Caliaro, G., et al.: J. Pharm. Biomed. Anal., 26, 427 (2001)
• Ulmeanu, S., et al.: Pharm. Res., 20, 1317 (2001)