beta-Eucaine

Title: b-Eucaine
CAS Registry Number: 500-34-5
CAS Name: 2,2,6-Trimethyl-4-piperidinol benzoate (ester)
Additional Names: a-4-benzoyloxy-2,2,6-trimethylpiperidine; a-vinyldiacetonalkamine benzoate; benzamine; betacaine; eucaine B
Molecular Formula: C15H21NO2
Molecular Weight: 247.33
Percent Composition: C 72.84%, H 8.56%, N 5.66%, O 12.94%
Literature References: Prepn from lower melting form (a-form) of 2,2,6-trimethyl-4-piperidinol and benzoyl chloride: Harries, Ann. 417, 107, see p 175 (1918). Stereochemistry: King, J. Chem. Soc. 125, 41 (1924); Stenlake, J. Pharm. Pharmacol. 6, 164 (1954). Configuration: Perks, Russell, ibid. 19, 318 (1966). Toxicity data: Hirschfelder, Physiol. Rev. 12, 262 (1932).
Properties: Crystals from petr ether, mp 70-71° (corr). MLD in frogs, rabbits (mg/kg): 1300, 400-500 s.c.; in rats, cats (mg/kg): 15-25, 10.0-12.5 i.v.; in guinea pigs (mg/kg): 310 s.c., 180 i.p., 30 i.v. (Hirschfelder).
Melting point: mp 70-71° (corr)
Toxicity data: MLD in frogs, rabbits (mg/kg): 1300, 400-500 s.c.; in rats, cats (mg/kg): 15-25, 10.0-12.5 i.v.; in guinea pigs (mg/kg): 310 s.c., 180 i.p., 30 i.v. (Hirschfelder)
Derivative Type: Hydrochloride
Properties: Crystals from water, mp 277-279° (corr). pKa 9.4. One gram dissolves in 30 ml water, 35 ml alcohol, 6 ml chloroform; more sol in boiling water or boiling alcohol. Aq soln is neutral to litmus.
Melting point: mp 277-279° (corr)
pKa: pKa 9.4
Derivative Type: d-Form
Properties: Crystals from petr ether, mp 57-58° (corr).
Melting point: mp 57-58° (corr)
Derivative Type: d-Form hydrochloride
Properties: [a]D +11.5° (water).
Optical Rotation: [a]D +11.5° (water)
Derivative Type: l-Form
Properties: Crystals from petr ether, mp 57-58° (corr).
Melting point: mp 57-58° (corr)
Derivative Type: l-Form hydrochloride
Properties: Crystals, mp 244-245° (corr). [a]D -11.3° (water).
Melting point: mp 244-245° (corr)
Optical Rotation: [a]D -11.3° (water)
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Has been used as a local anesthetic.
Keywords: Anesthetic (Local).
beta-Farnesene beta-Glucogallin beta-Glucuronidase beta-Hydroxybutyric Acid beta-Irone