(-)-Bupivacaine monohydrochloride

C₁₈H₂₉ClN₂OCAS 27262-48-2324.89 g/mol

Open in Covalent MOL file

Tertiary amine

Properties

Molecular formula: C₁₈H₂₉ClN₂O
Molar mass: 324.89 g/mol
Exact mass: 324.1968 Da
Melting point: 261.4 °C
logP: 4.97Crippen estimate
Polar surface area: 35.8 Å²
H-bond donors / acceptors: 1 / 2
Rotatable bonds: 5
Stereocentres: Sin SMILES atom order

Hazards

Danger

H300 Fatal if swallowed16.7% of notifiers
H310 Fatal in contact with skin14.6% of notifiers
H315 Causes skin irritation83.3% of notifiers
H319 Causes serious eye irritation83.3% of notifiers
H330 Fatal if inhaled14.6% of notifiers
H335 May cause respiratory irritation83.3% of notifiers

Aggregated from 48 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, P501

Identifiers

CAS number

27262-48-2

SMILES

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

InChIKey

SIEYLFHKZGLBNX-NTISSMGPSA-N

InChI

InChI=1S/C18H28N2O.ClH/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/t16-;/m0./s1

Weigh it out

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

Names and synonyms

8 names

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1), (2S)-
2′,6′-Pipecoloxylidide, 1-butyl-, monohydrochloride, (-)-
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (S)-
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (2S)-
(S)-(-)-Bupivacaine monohydrochloride
Chirocaine
Levobupivacaine hydrochloride
Popscaine

Work with (-)-Bupivacaine monohydrochloride

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.

Bupivacaine2180-92-9Free base, stereo not defined (-)-Bupivacaine27262-47-1Free base Bupivacaine hydrochloride18010-40-7Stereo not defined Bupivacaine hydrochloride14252-80-3Stereo not defined

Similar compounds

Ropivacaine hydrochloride98717-15-891 % similar Ropivacaine hydrochloride monohydrate132112-35-785 % similar Ropivacaine84057-95-484 % similar (+)-Ropivacaine98717-16-984 % similar Mepivacaine hydrochloride1722-62-969 % similar Mepivacaine22801-44-163 % similar 2′,6′-Pipecoloxylidide15883-20-247 % similar (2S)-N-(2,6-Dimethylphenyl)-2-piperidinecarboxamide27262-40-447 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

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