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Mepivacaine

Product Name
Mepivacaine
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
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Mepivacaine Property

pka
pKa 7.73(H2O,t =25±0.2,I=0.01(NaCl)) (Uncertain)
CAS DataBase Reference
22801-44-1(CAS DataBase Reference)
EPA Substance Registry System
2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl- (22801-44-1)
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Hazard and Precautionary Statements (GHS)

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Mepivacaine Chemical Properties,Usage,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

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Mepivacaine Suppliers

Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19997
Advantage
64
Shanghai Everchem Co., Ltd
Tel
86-29-81325371
Fax
+86-29-81325373
Email
info@everchem.cn
Country
China
ProdList
86
Advantage
62
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
Advantage
58
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810- ;025-57798810-
Fax
025-57019371
Email
sales@sunlidabio.com;sales@sunlidabio.com
Country
China
ProdList
3756
Advantage
55
Vientiane Tianjin Hengyuan Technology Co., Ltd.
Tel
15722085254
Fax
022-26358246
Email
phytochemical@126.com
Country
China
ProdList
813
Advantage
55
Finetech Industry Limited
Tel
027-87465837-
Fax
027-8777-2287
Email
sales@finetechnology-ind.com;
Country
China
ProdList
9375
Advantage
58
HangZhou YuHao Chemical Technology Co., Ltd.
Tel
0571-82693216
Fax
0571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
1853
Advantage
58
AN PharmaTech Co Ltd
Tel
86(21)68097365
Fax
86(21)33321566
Email
sales@anpharma.net
Country
China
ProdList
4907
Advantage
55
Giant chemicals
Tel
028-85434334-
Fax
QQ:245797092
Email
market@gianthx.com
Country
China
ProdList
4523
Advantage
56
ShangHai Siyan Biological Technology Co., Ltd.
Tel
021-50908862
Fax
021-50908862
Email
siyansales@126.com;442785678@qq.com
Country
China
ProdList
9628
Advantage
58
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View Lastest Price from Mepivacaine manufacturers

Wuhan Aoliqisi New Material Technology Co., Ltd.
Product
Mepivacaine 22801-44-1
Price
US $1.00/g
Min. Order
1000g
Purity
99%
Supply Ability
20ton/month
Release date
2021-07-08
Handan Tongyi New Material Technology Co., Ltd
Product
Mepivacaine hydorchloride 22801-44-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99.9%
Supply Ability
8000kgs/month
Release date
2021-04-02
Handan Tongyi New Material Technology Co., Ltd
Product
Mepivacaine Base 22801-44-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99.99%
Supply Ability
500kg/month
Release date
2021-03-01

22801-44-1, MepivacaineRelated 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