ChemicalBook
Chinese Japanese Germany Korea

Bupivacaine

Bupivacaine
Bupivacaine structure
CAS No.
2180-92-9
Chemical Name:
Bupivacaine
Synonyms
LAC-43;Anekain;MARCAINE;win11318;WIN 11318;BUPIVACAINE;Carbostesin;DL-Bupivacaine;BUPIVACAINE BASE;Bupivacaine (USP)
CBNumber:
CB4413068
Molecular Formula:
C18H28N2O
Formula Weight:
288.43
MOL File:
2180-92-9.mol

Bupivacaine Properties

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)
EWG's Food Scores
1
FDA UNII
Y8335394RO
NCI Dictionary of Cancer Terms
Marcaine
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)
SAFETY
  • Risk and Safety Statements
Hazard Codes  T+
Risk Statements  26/27/28-38-41
Safety Statements  22-26-36/37/39-45
RIDADR  2811

Bupivacaine Chemical Properties,Uses,Production

Originator

Carbostesin,Astra,W. Germany,1967

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.

Bupivacaine Preparation Products And Raw materials

Raw materials

Preparation Products


Bupivacaine Suppliers

Global( 146)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Hebei Ruishun Trade Co.,LTD
17052563120
Mike@rsbiology.com CHINA 301 58
Jinan Jianfeng Chemical Co., Ltd
15562555968
info@pharmachemm.com CHINA 304 58
Xingtai Haoxun Import and Export Trade Co., Ltd.
+8617733977883 WhatsApp:+8617733976525
86-0319-5021664 lisa@xthaoxun.com CHINA 297 58
Hebei Miaobian Biotechnology Co., Ltd
17733850068 +8617733850068
Iglesia@cnhbmiaobian.com CHINA 90 58
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21842 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22624 55
Hubei XinRunde Chemical Co., Ltd.
+8615102730682
02783214688 bruce@xrdchem.cn CHINA 568 55
Hebei Chishuo Biotechnology Co., Ltd.
13292891350 +86 311 66567340
luna@speedgainpharma.com CHINA 1007 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930501651
whatsapp: +8619930501651 breeduan@crovellbio.com CHINA 2586 58
hdzhl biotechnology co., ltd
86-13032617415
sales@luchibiology.com CHINA 1277 58

Related articles


View Lastest Price from Bupivacaine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-07-17 Bupivacaine
2180-92-9
US $1.00 / KG 1KG 99% 10tons Xingtai Haoxun Import and Export Trade Co., Ltd.
2020-07-20 bupivacaine
2180-92-9
US $60.00 / KG 10g 99%min 1tons Xingtai Haoxun Import and Export Trade Co., Ltd.
2020-09-21 Bupivacaine
2180-92-9
US $0.00 / KG 1KG 99.99 10 Ton Hebei Miaobian Biotechnology Co., Ltd

2180-92-9(Bupivacaine)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved