3894. β-Eucaine

Nomenclature

CAS number: 500-34-5
2,2,6-Trimethyl-4-piperidinol benzoate (ester); α-4-benzoyloxy-2,2,6-trimethylpiperidine; α-vinyldiacetonalkamine benzoate; benzamine; betacaine; eucaine B.
C15H21NO2; mol wt 247.33.
C 72.84%, H 8.56%, N 5.66%, O 12.94%.

Description and references

Prepn from lower melting form (α-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).

Chemical structure

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).

Derivative

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.

Derivative

d-Form.

Properties

Crystals from petr ether, mp 57-58° (corr).

Derivative

d-Form hydrochloride.

Properties

[α]D +11.5° (water).

Derivative

l-Form.

Properties

Crystals from petr ether, mp 57-58° (corr).

Derivative

l-Form hydrochloride.

Properties

Crystals, mp 244-245° (corr). [α]D -11.3° (water).

Therapeutic Category

Anesthetic (local).

Therapeutic Category (Veterinary)

Has been used as a local anesthetic.

Keywords

Anesthetic (Local)