Levobupivacaine

Product Name
Levobupivacaine
CAS No.
27262-47-1
Chemical Name
Levobupivacaine
Synonyms
Chirocaine;1-Butyl-N-(2;Levobupivacaine;Levobupivacaine base;1-Butyl-N-(2,6-dimet;Levobupivacaine free base;Levobupivacaine HCl (base);2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-;6-dimethylphenyl)-piperidine-2-carboxamide;Ropivacaine Impurity 40(Ropivacaine EP Impurity A)
CBNumber
CB52130881
Molecular Formula
C18H28N2O
Formula Weight
288.43
MOL File
27262-47-1.mol
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Levobupivacaine Property

Melting point:
136-137°C
alpha 
D25 -80.9° (c = 5 in methanol)
Boiling point:
430.65°C (rough estimate)
Density 
1.0238 (rough estimate)
refractive index 
1.5700 (estimate)
storage temp. 
Refrigerator
pka
14.85±0.70(Predicted)
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Hazard and Precautionary Statements (GHS)

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Levobupivacaine Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Chirocaine,Abbott Laboratories

Uses

Local anaesthetic used for epidural and intrathecal anaesthesia.

Manufacturing Process

Synthesis of L-pipecolic acid 2,6-xylidide (Patent US 4,695,576)
130 g of pipecolic acid and 158.6 g of Laevo (+)-tartaric acid are dissolved under stirring in 2 L 95% ethyl alcohol and 125 ml water at 80°C. The solution is allowed to cool to room temperature and after two days the crystallized D-pipecolic-tartrate is separated. The L-pipecolic-tartrate remains in solution. The filtrate is evaporated and dissolved in 5% acetic acid. Finally the solution is treated with Amberlite IR 45* in an ion exchanger. The eluate thus obtained is evaporated and the resulting crystalline residue is dried with potassium hydroxide in vacuo. The product obtained consists of L-pipecolic acid [α]D24 = -26.2°(C = 5, H2O).
4 g of phosphorus pentachloride was added to a suspension of 4 g of Lpipecolic acid hydrochloride in 40 ml acetylchloride. The initial reaction is effected at a temperature of about 35°C under stirring for 2 hours. The chlorination is completed by adding during a time period of about 10 minutes an additional two grams of phosphorus pentachloride and stirring over a further period of 4 hours while maintaining the suspension at a temperature of about 35°C. The resulting L-pipecolic acid chloride hydrochloride is filtered and washed with toluene and acetone. The crystalline residue is then dried in vacuo, m.p. 155°C.
A mixture of 2.7 ml 2,6-dimethylaniline, 4 ml acetone, and 4 ml Nmethylpyrrolidone is gradually added under stirring for 2 hours at 70°C to a suspension of 4 g of L-pipecolic acid chloride hydrochloride. This yields a crystalline product, which is filtered, washed with acetone and dried. This crystalline product is then dissolved in water and the base is precipitated by the addition of ammonia. The base is then extracted by the use of toluene and is recovered by evaporation. The base is recrystallized from a mixture of hexane and ethanol to yield L-pipecolic acid 2,6-xylidide. The melting point of this compound is 129-130°C.
Preparation of L-N-n-butylpipecilic acid 2,6-xylidide may de carried out by analogy with the preparation of L-N-n-propylpipecolic acid 2,6-xylidide (Patent US 5,777,124).
n-Butylbromide and potassium carbonate are added to a solution of L-pipecolic acid 2,6-xylidide dissolved in isopropyl alcohol. Thereafter, 5 ml of water is added to the mixture and the reaction is carried out for 4 hours at 72°C.
To complete the reaction, a further 0.8 ml n-butylbromide are added under continuous stirring and heating for 4 hours. The residue is treated with a mixture of 250 ml toluene and an equal amount of water at 50°C. The toluene layer is separated and washed three times with 100 ml warm water (40°C). A 175 ml portion of the toluene is removed by evaporation and the remainder is stored at +5°C for 6 hours to achieve crude crystalline L-N-n-butylpipecilic acid 2,6-xylidide. The crystalline product is separated by filtration, washed with some cooled toluene and dried at 70°C. Recrystallization may be carried from toluene. This product is dissolved in 100 ml ethanol and neutralized with concentrated hydrochloric acid. Ethanol is removed by evaporation and the hydrochloride product obtained is vacuum dried. Finally the latter is recrystallized from isopropyl alcohol.

Therapeutic Function

Local anesthetic

General Description

Levobupivacaine is the pure “S” enantiomer of bupivacaineand in vivo and in vitro studies confirm that it does notundergo metabolic inversion to R(+) bupivacaine. The pKaof the tertiary nitrogen is 8.09, the same as bupivacaine’s pKa. Levobupivacaine is available in solution for epiduraladministration, peripheral nerve block administration, andinfiltration anesthesia. Clinical trials have shown thatlevobupivacaine and bupivacaine have similar anestheticeffects. Levobupivacaine has lower CNS and cardiotoxicitythan bupivacaine although unintended intravenousinjection when performing nerve blocks may result intoxicity. Racemic bupivacaine is metabolized extensivelywith no unchanged drug found in the urine or feces. Liverenzymes including the CYP3A4 and CYP1A2 isoforms areresponsible for N-dealkylation and 3-hydroxylation oflevobupivacaine followed by glucuronidation or sulfation.

Levobupivacaine Preparation Products And Raw materials

Raw materials

Preparation Products

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Levobupivacaine Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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76
Chembest Research Laboratories Limited
Tel
021-20908456-
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
5948
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61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
9917
Advantage
62
Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19999
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64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32358
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50
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
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Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399-
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4575
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Shanghai TaoShu Biochemical Technology Co., Ltd.
Tel
021-33632979-
Fax
021-33632979
Email
service1@targetmol.com
Country
China
ProdList
7962
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58
Vientiane Tianjin Hengyuan Technology Co., Ltd.
Tel
15722085254
Fax
022-26358246
Email
phytochemical@126.com
Country
China
ProdList
813
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55
Chengdu HuaXia Chemical Reagent Co. Ltd
Tel
400-1166-196;028-84555506- ;028-84555506-
Fax
QQ:800101999
Email
cdhxsj@163.com;cdhxsj@163.com;cdhxsj@163.com
Country
China
ProdList
13362
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58
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View Lastest Price from Levobupivacaine manufacturers

Shanxi Lianxu New Material Co., LTD
Product
Levobupivacaine 27262-47-1
Price
US $8.00/KG
Min. Order
1KG
Purity
99.9%
Supply Ability
1000kg/month
Release date
2021-10-13
Zhuozhou Wenxi import and Export Co., Ltd
Product
Levobupivacaine 27262-47-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
career henan chemical co
Product
1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide 27262-47-1
Price
US $8.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10tons
Release date
2018-12-24

27262-47-1, LevobupivacaineRelated Search:


  • 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide
  • Chirocaine
  • Levobupivacaine
  • (2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2α-carboxamide
  • 2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-
  • 1-Butyl-N-(2,6-dimet
  • Levobupivacaine base
  • (2S)-1-Butyl-N-(2,6-diMethylphenyl)-2-piperidinecarboxaMide
  • Levobupivacaine HCl (base)
  • Levobupivacaine free base
  • 1-Butyl-N-(2
  • 6-dimethylphenyl)-piperidine-2-carboxamide
  • Ropivacaine Impurity 40(Ropivacaine EP Impurity A)
  • Bupivacaine impurity 12/ (S)-(-)-Bupivacaine/Levobupivacaine/Ropivacaine EP Impurity A/(2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • Ropivacaine impurity 1/ Ropivacaine EP Impurity A/(S)-(-)-Bupivacaine/Levobupivacaine/(2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • 27262-47-1
  • C18H32ClN2O
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  • Chiral Reagents
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  • Pharmaceuticals