Bupivacaine

C18H28N2OCAS 2180-92-9288.44 g/mol

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NONH
Tertiary amine

Properties

Molecular formula
C18H28N2O
Molar mass
288.44 g/mol
Exact mass
288.2202 Da
Melting point
107–108 °C
logP
4.55Crippen estimate
Polar surface area
35.8 Ų
H-bond donors / acceptors
1 / 2
Rotatable bonds
5

Hazards

No GHS classification is on file for this compound. That is not evidence that it is harmless.

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Identifiers

CAS number
2180-92-9
SMILES
CCCCN1CCCCC1C(O)=Nc1c(C)cccc1C
InChIKey
LEBVLXFERQHONN-UHFFFAOYSA-N
InChI
InChI=1S/C18H28N2O/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)

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Names and synonyms

15 names · show all
  • 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-
  • 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (±)-
  • 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
  • DL-Bupivacaine
  • (±)-Bupivacaine
  • Win 11318
  • 1-Butyl-2′,6′-pipecoloxylidide
  • Carbostesin
  • Marcaine
  • Bupivan
  • Anekain
  • Bucain
  • SKY 0402
  • Exparel
  • RS-Bupivacaine

Work with Bupivacaine

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

(-)-Bupivacaine27262-47-1Defined stereoisomer Bupivacaine hydrochloride18010-40-7Salt (-)-Bupivacaine monohydrochloride27262-48-2Salt, defined stereoisomer Bupivacaine hydrochloride14252-80-3Salt

Similar compounds

Ropivacaine84057-95-490 % similar (+)-Ropivacaine98717-16-990 % similar Ropivacaine hydrochloride98717-15-884 % similar Ropivacaine hydrochloride monohydrate132112-35-779 % similar Mepivacaine22801-44-167 % similar Mepivacaine hydrochloride1722-62-963 % similar 2′,6′-Pipecoloxylidide15883-20-250 % similar (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide27262-40-450 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

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