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27262-45-9

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Basic Information
CAS No.: 27262-45-9
Name: (R)-(+)-BUPIVACAINE HCL
Article Data: 14
Molecular Structure:
Molecular Structure of 27262-45-9 ((R)-(+)-BUPIVACAINE HCL)
Formula: C18H28 N2 O
Molecular Weight: 288.433
Synonyms: 2-Piperidinecarboxamide,1-butyl-N-(2,6-dimethylphenyl)-, (R)-; 2',6'-Pipecoloxylidide, 1-butyl-, (+)-(8CI); (+)-(R)-Bupivacaine; (+)-Bupivacaine; (R)-(+)-Bupivacaine;(R)-Bupivacaine; D-(+)-Bupivacaine; d-Bupivacaine
Density: 1.032 g/cm3
Boiling Point: 423.4 ºC
Flash Point: 209.9ºC
Safety: Poison by subcutaneous, intratracheal and intravenous routes. When heated to decomposition it emits toxic fumes of NOx. See other bupicaine or bupivacaine entries.
PSA: 32.34000
LogP: 3.90740
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Chemistry

Product Name: D(+)-Bupivacaine (CAS NO.27262-45-9)


Molecular Formula: C18H28N2O
Molecular Weight: 288.43g/mol
Mol File: 27262-45-9.mol
Boiling point:  423.4 °C at 760 mmHg 
Flash Point: 209.9 °C
Density: 1.032 g/cm3
Surface Tension: 41.5 dyne/cm
Enthalpy of Vaporization: 67.78 kJ/mol
Vapour Pressure: 2.24E-07 mmHg at 25°C
XLogP3-AA: 3.4
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of D(+)-Bupivacaine (CAS NO.27262-45-9):
  IUPAC Name: (2R)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
  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-/m1/s1 
  InChIKey: LEBVLXFERQHONN-MRXNPFEDSA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 7900ug/kg (7.9mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
mouse LD50 subcutaneous 30mg/kg (30mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rabbit LD50 intratracheal 10mg/kg (10mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rabbit LD50 parenteral > 120mg/kg (120mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976.
rabbit LDLo intravenous 5500ug/kg (5.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 intravenous 3800ug/kg (3.8mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 subcutaneous 38mg/kg (38mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.

Safety Profile

Poison by subcutaneous, intratracheal and intravenous routes. When heated to decomposition it emits toxic fumes of NOx. See other bupicaine or bupivacaine entries.

Specification

 D(+)-Bupivacaine ,its CAS NO. is 27262-45-9,the synonyms is 2',6'-Pipecoloxylidide, 1-butyl-, D-(+)- .