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Articaine

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Name

Articaine

EINECS 245-957-7
CAS No. 23964-58-1 Density 1.178 g/cm3
PSA 95.67000 LogP 2.63360
Solubility N/A Melting Point 175-176 °C
Formula C13H20N2O3S Boiling Point 440.6 °C at 760 mmHg
Molecular Weight 284.37 Flash Point 220.3 °C
Transport Information N/A Appearance White or white crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 23964-58-1 (Articaine) Hazard Symbols N/A
Synonyms

2-Thiophenecarboxylicacid, 4-methyl-3-[2-(propylamino)propionamido]-, methyl ester (8CI);Carticaine;

 

Articaine History

 Articaine (23964-58-1) was first synthetized by Rusching in 1969, and brought to the market in Germany by Hoechst AG under the brand name Ultracain. It was originally referred to as "carticaine" until 1984.In 1983 it was brought into the North American market, to Canada, under the name Ultracaine for dental use and distributed by Hoechst-Marion-Roussel.After Ultracaine's patent protection expired, new generic versions arrived to the Canadian market: Septanest, Astracaine,and Zorcaine.It was approved by the FDA in April 2000, and became available in the United States of America two months later under the brand name Septocaine with Epinephrine 1:100,000 (Septodont). Articaine (23964-58-1) became available in the United States in October of 2010.

Articaine Specification

The IUPAC name of Articaine is methyl 4-methyl-3-[2-(propylamino)propanoylamino]thiophene-2-carboxylate. With the CAS registry number 23964-58-1, it is also named as 4-Methyl-3-(2-(propylamino)propionamido)-2-thiophenecarboxylic acid, methyl ester. The classification codes are Anesthetic; Anesthetics; Anesthetics, Local; Central Nervous System Agents; Central Nervous System Depressants; Peripheral Nervous System Agents; Sensory System Agents. Articaine is white or white crystalline powder which is a new generation of dental local anesthetic and is the most widely used local anesthetic in a number of European countries and available in many countries around the world.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.91; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.2; (4)ACD/LogD (pH 7.4): 1.47; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 6.02; (7)ACD/KOC (pH 5.5): 2.05; (8)ACD/KOC (pH 7.4): 94.19; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.556; (13)Molar Refractivity: 77.59 cm3; (14)Molar Volume: 241.3 cm3; (15)Polarizability: 30.75×10-24 cm3; (16)Surface Tension: 43.8 dyne/cm; (17)Enthalpy of Vaporization: 69.78 kJ/mol; (18)Vapour Pressure: 5.79E-08 mmHg at 25°C; (19)Rotatable Bond Count: 7; (20)Tautomer Count: 4; (21)Exact Mass: 284.119463; (22)MonoIsotopic Mass: 284.119463; (23)Topological Polar Surface Area: 95.7; (24)Heavy Atom Count: 19; (25)Complexity: 325.

Uses of Articaine: It is especially used for surgical operation which is involving osteotomy and mucous membranes. And it is the only dental local anesthetic which is supplied in the domestic market. In addition, Articaine is generally made as injection with adrenaline. Besides, articaine is used both for infiltration and block injections in dentistry. 

People can use the following data to convert to the molecule structure. 
1. SMILES: O=C(Nc1c(scc1C)C(=O)OC)C(NCCC)C;
2. InChI: InChI=1/C13H20N2O3S/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4/h7,9,14H,5-6H2,1-4H3,(H,15,16).

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