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B5274

Supelco

Bupivacaine hydrochloride monohydrate

analytical standard, for drug analysis

Synonym(s):

1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide

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About This Item

Empirical Formula (Hill Notation):
C18H28N2O · HCl · H2O
CAS Number:
73360-54-0
Molecular Weight:
342.90
EC Number:
241-917-8
MDL number:
MFCD00941462
UNSPSC Code:
41116107
PubChem Substance ID:
329773253
NACRES:
NA.24

grade

analytical standard, for drug analysis

Quality Level

100

Assay

≥99%

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

SMILES string

O.Cl.CCCCN1CCCCC1C(=O)Nc2c(C)cccc2C

InChI

1S/C18H28N2O.ClH.H2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H;1H2

InChI key

HUCIWBPMHXGLFM-UHFFFAOYSA-N

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Application

Bupivacaine hydrochloride monohydrate may be used as an analytical standard for the determination of the bupivacaine in pharmaceutical preparations and plasma samples using chromatography techniques.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Sodium channel blocker, local anesthetic.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBZ5207
BCBW8645
BCBM7058V
BCBQ9309V
BCBQ9309

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Determination of free concentration of ropivacaine and bupivacaine in blood plasma by ultrafiltration and coupled-column liquid chromatography
Arvidsson T and Eklund E
Journal of Chromatography. B, Biomedical Sciences and Applications, 668(1), 91-98 (1995)
Huiyuan Zhang et al.
Drug design, development and therapy, 13, 1659-1666 (2019-06-14)
Background: Bupivacaine (Bup) is the most commonly used local anesthetic. However, Bup induces cytotoxicity, especially in older patients. Recent reports have indicated that andrographolide (Andro) exhibits protective effects on human neurons. Nevertheless, whether Andro can inhibit Bup-induced cytotoxicity remains unclear.
Kejian Shi et al.
Anesthesia and analgesia, 116(4), 804-809 (2013-03-06)
While lipid emulsion may reverse the systemic toxicity of bupivacaine, the pharmacokinetics and tissue distribution of bupivacaine after lipid emulsion infusion are not clear. In this study, we assessed the influence of lipid emulsion administration on the pharmacokinetics and tissue
Anna M Wiersma et al.
Bio-protocol, 8(10), e2862-e2862 (2018-05-20)
When injected into the motor cortex of rats, anterograde tracers label fibers of the associated descending corticospinal tract (CST) that originate from pyramidal neurons in the tracer-injected cortex. These fibers can be assessed at the level of the spinal cord
Ilin Kuo et al.
Anesthesiology, 118(6), 1350-1361 (2013-03-06)
In vitro observations support the lipid sink theory of therapeutic action by confirming the capacity of lipid emulsions to successfully uptake bupivacaine from aqueous media. However, competing hypotheses and some in/ex vivo small animal studies suggest that a metabolic or
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