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Mepivacaine

Mepivacaine
Mepivacaine structure
CAS No.
22801-44-1
Chemical Name:
Mepivacaine
Synonyms
MEPIVACAINE;A pp because;MepivacaineBase;Mepivacaine USP/EP/BP;Mepivacaine Impurity A;Mepivacaine HCl (base);Mepivacaine hydorchloride;Trimethocaine hydrochloride;Mepivacaine(Cas number22801-44-1);N-(2,6-Dimethylphenyl)-1-Piperidinecarboxamide
CBNumber:
CB8460318
Molecular Formula:
C15H22N2O
Formula Weight:
246.35
MOL File:
22801-44-1.mol

Mepivacaine Properties

pka
pKa 7.73(H2O,t =25±0.2,I=0.01(NaCl)) (Uncertain)
CAS DataBase Reference
22801-44-1(CAS DataBase Reference)
FDA UNII
B6E06QE59J
ATC code
N01BB03,N01BB53
EPA Substance Registry System
2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (22801-44-1)

Mepivacaine Chemical Properties,Uses,Production

Originator

Carboraine,Winthrop,US,1960

Uses

Local anesthetic.

Manufacturing Process

Ethyl magnesium bromide is prepared in the usual way by reacting 185 parts by weight of ethyl bromide in 800 parts of anhydrous ether with 37 parts by weight of magnesium turnings. Under vigorous stirring 121 parts of 2,6- dimethyl aniline are added at a rate depending on the vigor of the gas evaporation. When the evolution of gas has ceased, 85 parts by weight of Nmethylpipecolic acid ethyl ester are added to the 2,6-dimethyl aniline magnesium bromide slurry. The mixture is refluxed for ? hour with continued stirring, after which it is cooled down. Dilute hydrochloric acid is added carefully in order to dissolve and hydrolyze the magnesium compound formed.
The pH is adjusted to 5.5 and the water phase separated and extracted with additional ether in order to remove the surplus dimethyl aniline. After addition of an excess of ammonia to the solution, the reaction product, Nmethylpipecolic acid 2,6-dimethyl anilide, is recovered by extraction with isoamyl alcohol. The isoamyl alcohol solution is evaporated to dryness, the product dissolved in dilute hydrochloric acid, treated with charcoal and reprecipitated with NaOH. N-methylpipecolic acid 2,6-dimethyl anilide is obtained in crystalline form.

Therapeutic Function

Local anesthetic

General Description

Mepivacaine hydrochloride is available in 1% to 3% solutionsand is indicated for infiltration anesthesia, dental procedures,peripheral nerve block, or epidural block. The onset of anesthesiais rapid, ranging from about 3 to 20 minutes for sensoryblock. Mepivacaine is rapidly metabolized in the liver with50% of the administered dose excreted into the bile asmetabolites. The metabolites are reabsorbed in the intestineand excreted in the kidney with only a small percentage foundin the feces. Less than 5% to 10% of the administered dose isfound unchanged in the urine. The primary metabolic productsare the N-demethylated metabolite and the 3 and 4 phenolicmetabolites excreted as their glucuronide conjugates.

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.

Chemical Synthesis

Mepivacaine is N-(2,6-dimethylphenyl)-1-methyl-2-piperindincarboxamide (2.2.3). Two primary methods of synthesis have been suggested. According to the first, mepivacaine is synthesized by reacting the ethyl ester of 1-methylpiperindine-2-carboxylic acid with 2,6-dimethylanilinomagnesium bromide, which is synthesized from 2,6- dimethylaniline and ethylmagnesium bromide [12–14].

According to the figure below, reacting 2,6-dimethylaniline with the acid chloride of pyridine-carboxylic acid first gives the 2,6-xylidide of α-picolinic acid (2.2.4). Then the aromatic pyridine ring is reduced to piperidine by hydrogen in the presence of a platinum on carbon catalyst. The resulting 2,6-xylidide α-pipecolinic acid (2.2.5) is methylated to mepivacaine using formaldehyde with simultaneous reduction by hydrogen in the presence of platinum on carbon catalyst [15].

Metabolism

Mepivacaine undergoes extensive hepatic metabolism catalyzed by CYP1A2, with only a small percentage of the administered dosage (<10%) being excreted unchanged in the urine. The major metabolic biotransformations of mepivacaine are N-dealkylation (to give the N-demethylated compound 2′,6′-pipecoloxylidide) and aromatic hydroxylations. These metabolites are excreted as their corresponding glucuronides.

Mepivacaine Preparation Products And Raw materials

Raw materials

Preparation Products


Mepivacaine Suppliers

Global( 100)Suppliers
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0086 15232103582
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sales@conier.com China 47498 58
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+8613111626072 (WhatsApp)
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Related articles

  • What is Mepivacaine?
  • Mepivacaine hydrochloride [N-(2, 6-dimethylphenyl)-1-methyl 2-piperidinecarboxamide monohydrochloride] is an amino amide-type ....
  • Oct 9,2020

View Lastest Price from Mepivacaine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-01-24 Mepivacaine
22801-44-1
US $9.90-9.90 / g/Bag 10g/Bag 99.99%HPLC.USP42——Powder、Oil、Pills、Capsules、Tablets,Customized packaging 100KG Wuhan Biocar Pharmacy Co., Ltd.
2022-01-24 Mepivacaine
22801-44-1
US $40.00-90.00 / KG 0.5KG >99% 20tons Anhui Rencheng Technology Co., Ltd
2022-01-21 Mepivacaine
22801-44-1
US $1.00 / g 1000g 99% 20ton/month Wuhan Aoliqisi New Material Technology Co., Ltd.

22801-44-1(Mepivacaine)Related Search:


  • MEPIVACAINE
  • N-(2,6-Dimethylphenyl)-1-Piperidinecarboxamide
  • N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide
  • MepivacaineBase
  • Mepivacaine HCl (base)
  • Mepivacaine N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide
  • Mepivacaine(Cas number22801-44-1)
  • N-(2,6-dimethylphenyl)-1-methyl-2-piperidinecarboxamide
  • Mepivacaine Impurity A
  • Mepivacaine hydorchloride
  • A pp because
  • Mepivacaine USP/EP/BP
  • Trimethocaine hydrochloride
  • 22801-44-1
  • C15H22N2O
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