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Bupivacaine

Athanor · official

C18H28N2O · 288.4 g/mol

IUPAC name: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Also called Marcaine, Sensorcaine, local anaesthetic

DrugsRings
Open in Athanor
The structure of Bupivacaine
Drawn from its SMILES with RDKit
Acute toxicityHealth hazardDangerFatal if swallowed, in contact with skin or if inhaled · Fatal if swallowed · Toxic if swallowed · Fatal in contact with skin · Toxic in contact with skin · Fatal if inhaled · Causes damage to organs

Names and identifiers

IUPAC name
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Synonyms
Marcaine, Sensorcaine, local anaesthetic
+ 39 more

Levobupivacaine, (S)-bupivacaine, (-)-bupivacaine, L-(-)-bupivacaine, (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide, Levobupivacaina, Novabupi, (S)-1-Butyl-2',6'-pipecoloxylidide, L-bupivacaine, Bupivacaine, (s)-, Bupivacaine, (-)-, L-(-)-1-Butyl-2',6'-pipecoloxylidide, A5H73K9U3W, CHEBI:6149, DTXSID8048496, 2',6'-Pipecoloxylidide, 1-butyl-, L-(-)-, 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-, (s)-1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide, (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboximidic acid, levobupivacainum, Bupivacaine (-)-, RefChem:153196, DTXCID8028470, N01BB10, 690-076-7, L(-)-Bupivacaine, (S)-(-)-Bupivacaine, (S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide, (2S)-1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, Bupivacaine (-)-form, Levobupivacaine (INN), MFCD00936851, LEVOBUPIVACAINE [INN], Levobupivacaine [INN:BAN], Levobupivacaine free base, Novabupi (TN), NCGC00159482-02, UNII-A5H73K9U3W, 27262-47-1 (free base)

Molecular formula
C18H28N2O
Empirical formula
C18H28N2O
Molecular weight
288.4 g/mol
Exact mass
288.22016
CAS number
2180-92-9
PubChem CID
92253
Canonical SMILES
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
Isomeric SMILES
CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
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
InChIKey
LEBVLXFERQHONN-INIZCTEOSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
21
Rings
2
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.61
H-bond donors
1
H-bond acceptors
2
Rotatable bonds
5
TPSA (Ų)
32.3
Formal charge
0
XLogP3
3.4 PubChem
Complexity
321 PubChem
Stereocenters
1 definedCIP: C10: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C74.96%
  • H9.79%
  • N9.71%
  • O5.55%

Isotope pattern

100%288.22021%289.2232.2%290.226291.229

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
3.9 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-3.96 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
2.37 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 288.44
  • log P ≤ 5 (Crippen): 3.9
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 2

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 3 company reports to ECHA. Source [1].

  • Acute toxicity
  • Health hazard
  • H300+H310+H330Fatal if swallowed, in contact with skin or if inhaled (33.3% of reports)
  • H300Fatal if swallowed (33.3% of reports)
  • H301Toxic if swallowed (33.3% of reports)
  • H310Fatal in contact with skin (33.3% of reports)
  • H311Toxic in contact with skin (33.3% of reports)
  • H330Fatal if inhaled (66.7% of reports)
  • H370Causes damage to organs (33.3% of reports)

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

Safety data sheets on the supplier’s page: AA BLOCKS, BOC Sciences, MuseChem.

Always read the supplier’s safety data sheet before working with it.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  3. ·Literature on PubChem

Data last updated 2026-10-14.