(-)-Bupivacaine

C₁₈H₂₈N₂OCAS 27262-47-1288.44 g/mol

Open in Covalent MOL file

Properties

Molecular formula: C₁₈H₂₈N₂O
Molar mass: 288.44 g/mol
Exact mass: 288.2202 Da
Melting point: 135–137 °C
logP: 4.55Crippen estimate
Polar surface area: 35.8 Å²
H-bond donors / acceptors: 1 / 2
Rotatable bonds: 5
Stereocentres: Sin SMILES atom order

Hazards

Danger

H300+H310+H330 Fatal if swallowed, in contact with skin or if inhaled33.3% of notifiers
H300 Fatal if swallowed33.3% of notifiers
H301 Toxic if swallowed33.3% of notifiers
H310 Fatal in contact with skin33.3% of notifiers
H311 Toxic in contact with skin33.3% of notifiers
H330 Fatal if inhaled66.7% of notifiers
H370 Causes damage to organs33.3% of notifiers

Aggregated from 3 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P308+P316, P316, P320, P321, P330, P361+P364, P403+P233, P405, P501

Identifiers

CAS number

27262-47-1

SMILES

CCCCN1CCCC[C@H]1C(O)=Nc1c(C)cccc1C

InChIKey

LEBVLXFERQHONN-INIZCTEOSA-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)/t16-/m0/s1

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

11 names

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-
2′,6′-Pipecoloxylidide, 1-butyl-, (-)-
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (S)-
(2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide
L-(-)-Bupivacaine
(S)-Bupivacaine
(S)-(-)-Bupivacaine
Levobupivacaine
(-)-(S)-Bupivacaine
Chirocain
(2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

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.

Bupivacaine2180-92-9Stereo not defined Bupivacaine hydrochloride18010-40-7Salt, stereo not defined (-)-Bupivacaine monohydrochloride27262-48-2Salt Bupivacaine hydrochloride14252-80-3Salt, stereo not defined

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

PubChem CAS Common Chemistry NIST WebBook