Mepivacaine

Base Information

• Chemical Name: Mepivacaine
• CAS No.: 22801-44-1
• Molecular Formula: C15H22N2O
• Molecular Weight: 246.35
• Mol file: 22801-44-1.mol

Synonyms:2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-;N-(2,6-Dimethylphenyl)-1-methyl-2-piperidinecarboxamide;DL-Mepivacaine;

Chemical Property of Mepivacaine

Chemical Property:

• Vapor Pressure: 4.52E-06mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 383.1 °C at 760 mmHg
• PKA: pKa 7.73(H2O,t =25±0.2,I=0.01(NaCl)) (Uncertain)
• Flash Point: 185.5 °C
• PSA: 32.34000
• Density: 1.077 g/cm³
• LogP: 2.73710
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Mepivacaine can be used in biological study of 2-adamantanamine produces prolonged spinal block in rats. Local anesthetic.
• Therapeutic Function: Local anesthetic
• Clinical Use: Mepivacaine hydrochloride [N-(2, 6-dimethylphenyl)-1-methyl 2-piperidinecarboxamide monohydrochloride] is an amino amide-type local anesthetic agent widely used to provide regional analgesia and anesthesia by local infiltration, peripheral nerve block, and epidural and caudal blocks. The pharmacological and toxicological profile of mepivacaine is quite similar to that of lidocaine, except that mepivacaine has a slightly longer duration of action and lacks the vasodilator activity of lidocaine. For this reason, it serves as an alternate choice for lidocaine when addition of epinephrine is not recommended in patients with hypertensive vascular disease.

Technology Process of Mepivacaine

There total 17 articles about Mepivacaine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) (39627-98-0) → mepivacaine (96-88-8,22801-44-1,24358-84-7,34811-66-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; water; at 50 ℃;

DOI:10.1002/ejoc.201700824

Reference yield: 53.0%

N-methylcyclohexylamine (626-67-5) + 2,5-dimethylphenyl isocyanate (40397-98-6) → N-(2,6-dimethylphenyl)-1-(2-(2,6-dimethylphenylamino)-2-oxoethyl)piperidine-2-carboxamide + N2,N6-bis(2,6-dimethylphenyl)-1-methylpiperidine-2,6-dicarboxamide + mepivacaine (96-88-8,22801-44-1,24358-84-7,34811-66-0) + N-(2,6-dimethylphenyl)-2-(piperidin-1-yl)acetamide (13327-12-3)

Guidance literature:

With triethyl borane; oxygen; at 20 ℃; for 37h; Further byproducts.;

DOI:10.1021/ol7023295

Reference yield:

methanol (67-56-1) + 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) (39627-98-0) → 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5) + mepivacaine (96-88-8,22801-44-1,24358-84-7,34811-66-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; at 70 ℃; under 37503.8 Torr; Temperature;

DOI:10.1002/ejoc.201700824

upstream raw materials:

2-(2,6-dimethyl-phenylcarbamoyl)-1-methyl-pyridinium; iodide

dimethyl sulfate

N-methylcyclohexylamine

2,5-dimethylphenyl isocyanate

Refernces

• 1、 Suveges, Nícolas S.,de Souza, Rodrigo O. M. A.,Gutmann, Bernhard,Kappe, C. Oliver. "Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy". . p. 6511 - 6517. Retrieved 2017/12/02.
• 2、 Shankaraiah, Nagula,Pilli, Ronaldo Aloise,Santos, Leonardo S.. "Enantioselective total syntheses of ropivacaine and its analogues". . p. 5098 - 5100. Retrieved 2008/12/21.