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Molecule
(-)-Bupivacaine
CAS: 27262-47-1 · C18H28N2O
2D Structure
3D Structure
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Basic Information
- CAS Registry Number
- 27262-47-1
- Molecular Formula
- C18H28N2O
- Molecular Mass
- 288.43 g/mol
Identifiers
CAS Registry Number
27262-47-1
SMILES
CCCCN1CCCC[C@H]1C(O)=Nc1c(C)cccc1C
InChI Key
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
Names and Synonyms
- (-)-Bupivacaine Common Name
- 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)- Synonym
- 2′,6′-Pipecoloxylidide, 1-butyl-, (-)- Synonym
- 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (S)- Synonym
- (2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide Synonym
- (-)-Bupivacaine Synonym
- L-(-)-Bupivacaine Synonym
- (S)-Bupivacaine Synonym
- (S)-(-)-Bupivacaine Synonym
- Levobupivacaine Synonym
- (-)-(S)-Bupivacaine Synonym
- Chirocain Synonym
- (2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Synonym
All Properties
Comprehensive physical and chemical properties
| Property | Value | Source |
|---|---|---|
| Molecular Mass | 288.43 g/mol | CAS Common Chemistry |
| 288.43500000000006 g/mol | RDKit | |
| 288.435 g/mol | RDKit | |
| Canonical SMILES | O=C(NC=1C(=CC=CC1C)C)C2N(CCCC)CCCC2 | CAS Common Chemistry |
| 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 | CAS Common Chemistry |
| InChI Key | InChIKey=LEBVLXFERQHONN-INIZCTEOSA-N | CAS Common Chemistry |
| Melting Point | 135-137 °C | CAS Common Chemistry |
| Name | (-)-Bupivacaine | CAS Common Chemistry |
| Heavy Atom Count | 21 | RDKit |
| Hydrogen Bond Acceptors | 2 | RDKit |
| Hydrogen Bond Donors | 1 | RDKit |
| Rotatable Bonds | 5 | RDKit |
| Aromatic Ring Count | 1 | RDKit |
| Topological Polar Surface Area | 35.83 Ų | RDKit |
| 35.6 Ų | chempirical lib | |
| LogP | 4.546040000000004 | RDKit |
| 4.546 | RDKit | |
| 4.4 | chempirical lib | |
| Molar Refractivity | 89.75980000000006 cm³/mol | RDKit |
| Ring Count | 2 | RDKit |
| Formal Charge | 0 | RDKit |
| Fraction Csp3 | 0.6111 | RDKit |
| 0.61 | chempirical lib | |
| Exact Mass | 288.22016351599996 g/mol | RDKit |
Spectral Data
NMR, IR, and Mass spectral data
Predicting NMR spectra...
10 ppm
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3
2
1
0 ppm
| Shift (ppm) | Multiplicity | Integration | Assignment |
|---|
200 ppm
180
160
140
120
100
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40
20
0 ppm
| Shift (ppm) | DEPT | Assignment |
|---|
Note: These NMR spectra are predicted computationally and may differ from experimental data. Predictions are based on chemical environment analysis.
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MW = 288.43 g/mol. Edit any field — others recompute live.
