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(S)-(-)-Bupivacaine

CAT: 0572-TRC-B689546-100MGSize: 100 mgDry Ice: NoHazardous: No
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CAT#:0572-TRC-B689546-100MGSize:100 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
27262-47-1
Synonyms
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (S)-; 2',6'-Pipecoloxylidide, 1-butyl-, (-)- (8CI); (2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; (-)-(S)-Bupivacaine; (-)-Bupivacaine; (S)-(-)-Bupivacaine; (S)-Bupivacaine; Chirocain; L-(-)-Bupivacaine; Levobupivacaine
Hazard Statement
Fatal if inhaled; UN number: UN2811; Packing Group: II
Purity
>95% (HPLC)
Smiles
CCCCN1CCCC[C@H]1C(=O)Nc2c(C)cccc2C
Molecular Formula
C18 H28 N2 O
Molecular Weight
288.43
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
Additionnal Information
IUPAC name: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Shipping Conditions
Room Temperature
Storage Conditions
+4°C

Chemical Information

Levobupivacaine

Levobupivacaine is the (S)-()-enantiomer of bupivacaine. It has a role as a local anaesthetic, an EC 3.1.1.8 (cholinesterase) inhibitor, an adrenergic antagonist, an amphiphile and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is a conjugate base of a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine.

CAS Number27262-47-1
PubChem CID92253
IUPAC Name(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Molecular FormulaC18H28N2O
Molecular Weight288.4
XLogP3.4
Topological Polar Surface Area32.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count21
Formal Charge0
Complexity321
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
Chemical Structure
2D Structure
2D structure of Levobupivacaine
CAS: 27262-47-1
CID: 92253
Formula: C18H28N2O
MW: 288.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight288.4
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass288.220163521
Monoisotopic Mass288.220163521
Topological Polar Surface Area32.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity321
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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