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R0283

Sigma-Aldrich

Ropivacaine hydrochloride monohydrate

≥98% (HPLC)

Synonym(s):

(2S)-N-(2,6-dimethylphenyl)-1-propyl-2-piperidinecarboxamide hydrochloride monohydrate, (S)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide hydrochloride monohydrate, Naropin hydrochloride monohydrate

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About This Item

Empirical Formula (Hill Notation):
C17H26N2O · HCl · H2O
CAS Number:
132112-35-7
Molecular Weight:
328.88
MDL number:
MFCD00946578
UNSPSC Code:
12352203
PubChem Substance ID:
329823983
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -9 to -12, c = 1 in methanol

storage condition

desiccated

color

white to off-white

solubility

H2O: 5 mg/mL, clear

originator

AstraZeneca

storage temp.

2-8°C

SMILES string

O.Cl.CCCN1CCCC[C@H]1C(=O)Nc2c(C)cccc2C

InChI

1S/C17H26N2O.ClH.H2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3;;/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20);1H;1H2/t15-;;/m0../s1

InChI key

VSHFRHVKMYGBJL-CKUXDGONSA-N

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General description

Ropivacaine has lidocaine-related structure with tertiary amine side chains. It is a pure S(-)enantiomer with a propyl group on the piperidine nitrogen atom.

Application

Ropivacaine hydrochloride monohydrate has been used as an analyte in tandem mass spectrometry and as an amide-based local anaesthetic to test its effect on breast cancer cell methylation.

Biochem/physiol Actions

Local anaesthetic with less cardiotoxicity than bupivacaine; causes reversible blockade of impulse propagation along nerve fibres by preventing the inward movement of sodium ions through the cell membrane of the nerve fibers.
Ropivacaine less lipophilic as compared with bupivacaine. It is metabolized in the liver by the enzyme cytochrome P4501A2. Ropivacaine elicits less central nervous system (CNS) toxicity and is used as a local anaesthetic during postoperative and labour pain.

Features and Benefits

This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bupivacaine hydrochloride United States Pharmacopeia (USP) Reference Standard

USP

1078507

Bupivacaine hydrochloride

USP

USP

1605512

Ropivacaine Related Compound A

Lidocaine powder

Sigma-Aldrich

L7757

Lidocaine

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British journal of anaesthesia, 113 Suppl 1, i32-i38 (2014-06-21)
Lidocaine demethylates deoxyribonucleic acid (DNA) in breast cancer cells. This modification of epigenetic information may be of therapeutic relevance in the perioperative period, because a decrease in methylation can reactivate tumour suppressor genes and inhibit tumour growth. The objectives of
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