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Bupivacaine

Product Name
Bupivacaine
CAS No.
2180-92-9
Chemical Name
Bupivacaine
Synonyms
LAC-43;Anekain;MARCAINE;win11318;WIN 11318;BUPIVACAINE;Carbostesin;DL-Bupivacaine;Cloth than paid;BUPIVACAINE BASE
CBNumber
CB4413068
Molecular Formula
C18H28N2O
Formula Weight
288.43
MOL File
2180-92-9.mol
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Bupivacaine Property

Melting point:
107.5-108°
Boiling point:
430.65°C (rough estimate)
Density 
1.0238 (rough estimate)
refractive index 
1.5700 (estimate)
pka
8.09; also reported as 8.17(at 25℃)
Water Solubility 
101.5mg/L(25 ºC)
CAS DataBase Reference
2180-92-9(CAS DataBase Reference)
NIST Chemistry Reference
2-Piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-(2180-92-9)
EPA Substance Registry System
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)- (2180-92-9)
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Safety

Hazard Codes 
T+
Risk Statements 
26/27/28-38-41
Safety Statements 
22-26-36/37/39-45
RIDADR 
2811
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Hazard and Precautionary Statements (GHS)

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Bupivacaine Chemical Properties,Usage,Production

Originator

Carbostesin,Astra,W. Germany,1967

Uses

Like lidocaine and mepivacaine, bupivacaine is used in infiltration, spinal, and epidural anesthesia in blocking nerve transmission. Its most distinctive property is its long-lasting action. It is used for surgical intervention in urology and in lower thoracic surgery from 3 to 5 h in length, and in abdominal surgery lasting from 45 to 60 min. It is used to block the trifacial nerve, the sacral and brachial plexuses, in resetting dislocations, in epidural anesthesia, and during Cesarian sections.

Uses

Anesthetic (local).

Manufacturing Process

121 parts by weight of 2.6-xylidine are heated with 400 parts of diethylmalonate at 160°C for 1 hour, and the alcohol formed by the reaction is allowed to distill off. Thereafter the reaction mass is cooled to 80°C, and 500 parts of alcohol are added. After cooling the dixylidide is sucked off, and the alcohol solution with malonic ester monoxylidide is poured into 2,000 parts of water. The monoxylidide precipitates, is filtered off and washed with water, and recrystallized in diluted alcohol. Nitrosation thereafter takes place by dissolving the dried monoxylidide in chloroform and by introducing nitrosyl chloride at 0°C until the nitrosation is completed. The isonitrosomalonic ester xylidide is filtered off and dried. Thereafter the reduction takes place with zinc powder and formic acid at 90°-100°C.
The formic acid is distilled off, and the remainder dissolved in warm benzene and washed with a bicarbonate solution to a neutral reaction. After the benzene has been distilled off, the aminomalonic ester xylidide is obtained. This is treated with an equal quantity of sodium ethylate and boiled with twice the theoretical quantity of tetramethylene bromide in absolute alcohol. After 6 hours of boiling, the sodium bromide formed is separated, and the mixture is steamdistilled in order to remove the excess of tetramethylene bromide. The remaining oil, which mainly consists of deltabromobutylaminomalonic ester xylidide is separated from the water and boiled with 3 parts of concentrated hydrochloric acid for 3 hours. Thereafter carbonfiltering and evaporation to dryness under vacuum takes place. The residue is dissolved in water, and the pH adjusted with sodium hydroxide to 5.5. The solution is extracted twice with ether, and the water is made strongly alkaline with sodium hydroxide.
The oil precipitates and is crystallized after a time. The crystals are separated and dried under vacuum. The pipecolyl-2,6-xylidide produced is alkylated by boiling for 10-20 hours with 0.6 part n-butylbromide in an n-butanol solution in the presence of 0.5 part potassium carbonate. The potassium carbonate is filtered off and the butanol is distilled off in vacuum. The residue is dissolved in diluted hydrochloric acid and carbon treated, after which the base is precipitated with sodium hydroxide in the form of white crystals, which are filtered off and washed with water. The base obtained, which consists of N-n-butyl-pipecolyl-2,6-xylidide is sufficiently pure for the production of salts.

brand name

Marcaine (Hospira); Sensorcaine (AstraZeneca).

Therapeutic Function

Local anesthetic

General Description

Bupivacaine was synthesized simultaneously with mepivacainein 1957 but was at first overlooked because of the increasedtoxicity compared with mepivacaine. When themethyl on the cyclic amine of mepivacaine is exchanged fora butyl group the lipophilicity, potency and the duration ofaction all increase. Literature reports of cardiovascular toxicity,including severe hypotension and bradycardia, areabundant in the literature.91 Bupivacaine is highly bound toplasma proteins (95%), and thus the free concentration mayremain low until all of the protein binding sites are occupied.After that point, the plasma levels of bupivacaine rise rapidlyand patients may progress to overt cardiac toxicity withoutever showing signs of CNS toxicity. The cardiotoxicity ofbupivacaine is a result of its affinity to cardiac tissues and itsability to depress electrical conduction and predispose theheart to reentry types of arrhythmias. The cardiotoxicity ofbupivacaine was found to be significantly more prominentwith the “R” isomer, or the racemic mixture, thus the “S”stereoisomer is now on the market as levobupivacaine.

Chemical Synthesis

Bupivacaine, N-2,6-(dimethyl)1-butyl-2-piperidincarboxamide (2.2.7), is chemically similar to mepivacaine and only differs in the replacement of the N-methyl substituent on the piperidine ring with an N-butyl substituent. There are also two suggested methods of synthesis. The first comes from α-picolin-2,6-xylidide (2.2.4). The alkylation of the last with butyl bromide gives the corresponding pyridine salt (2.2.6). Finally, it is reduced by hydrogen using platinum oxide as a catalyst into a piperidine derivative—bupivacaine.

The other method results directly from the piperidine-2-carboxylic acid chloride, which is reacted with 2,6-dimethylaniline. The resulting amide (2.2.8) is further alkylated with butyl bromide to bupivacaine [17–19].

Bupivacaine Preparation Products And Raw materials

Raw materials

Preparation Products

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Bupivacaine Suppliers

Anhui Rencheng Technology Co., Ltd
Tel
Email
admin@ahrencheng.com
Country
China
ProdList
42
Advantage
58
Changzhou Sunchem Pharmaceutical Chemical Material Co.,Ltd.
Tel
0519-85195575- ; ;0519-85195565-
Fax
85195585
Email
850305@sunkechem.com;850305@sunkechem.com;850306@sunkechme.com
Country
China
ProdList
88
Advantage
69
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057-
Fax
0757-86311057
Email
sales.gd@hwrkchemical.com
Country
China
ProdList
17295
Advantage
55
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
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19993
Advantage
64
Dalian Meilun Biotech Co., Ltd.
Tel
0411-66864596- ;0411-66864952-
Email
sales@meilune.com;sales@meilune.com
Country
China
ProdList
3573
Advantage
58
S.Z. PhyStandard Bio-Tech. Co., Ltd.
Tel
;
Fax
0755 28094224
Email
3001280422@qq.com;marketing@phystandard.com
Country
China
ProdList
4945
Advantage
50
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
Advantage
58
NCE Biomedical Co.,Ltd.
Tel
4000-027-021 |24 hour enquiry :+86-13986109188 |English:+86-15623472865 |Japanese:+81-08033611988
Fax
+86-27-87599188
Email
sales@ncebiomed.com
Country
China
ProdList
1496
Advantage
55
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View Lastest Price from Bupivacaine manufacturers

WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Bupivacaine
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2021-01-16
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Bupivacaine 2180-92-9
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-27
Handan Tongyi New Material Technology Co., Ltd
Product
Bupivacaine 2180-92-9
Price
US $10.00/KG
Min. Order
1KG
Purity
99.99
Supply Ability
500kg/month
Release date
2021-03-10

2180-92-9, BupivacaineRelated Search:


  • MARCAINE
  • BUPIVACAINE
  • BUPIVACAINE BASE
  • 2',6'-Pipecoloxylidide, 1-butyl-
  • 6’-pipecoloxylidide,1-butyl-2
  • Anekain
  • Carbostesin
  • DL-Bupivacaine
  • LAC-43
  • WIN 11318
  • win11318
  • (.+/-.)-1-Butyl-2',6'-pipecoloxylidide
  • 1-Butyl-2-(2,6-xylycarbamoyl)piperidine
  • 1-Butyl-2',6'-pipecoloxylidide
  • 1-butyl-2’,6’-pipecoloxylidide
  • 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamid
  • 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • Bupivacaine Base & HCL
  • Levobupivacaine (Bupivacaine)
  • Bupivacaine anhydrous
  • Bupivacaine (USP)
  • Bupivacaine HCl (base)
  • 1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
  • Local Anesthetic Bupivacaine Powder
  • Cloth than paid
  • Bupivacaine USP/EP/BP
  • ()-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
  • 2180-92-9
  • 180-92-9
  • 2810-92-9
  • C18H28N2O
  • research chemical
  • Active Pharmaceutical Ingredients