3208. Dimenoxadol

Nomenclature

CAS number: 509-78-4
α-Ethoxy-α-phenylbenzeneacetic acid 2-(dimethylamino)ethyl ester; ethoxydiphenylacetic acid 2-dimethylaminoethyl ester; α,α-diphenyl-α-ethoxyacetic acid β-dimethylaminoethyl ester; 2-dimethylaminoethyl ethoxydiphenylacetate.
C20H25NO3; mol wt 327.42.
C 73.37%, H 7.70%, N 4.28%, O 14.66%.

Description and references

Opioid analgesic. Prepd by the reaction of diphenylethoxyacetic acid with dimethylchloroethylamine in the presence of isopropanol: Klosa, Arch. Pharm. 288, 42 (1955). Improved prepn: C. N. Yakhontov et al., Pharm. Chem. J. 8, 189 (1974). HPLC determn: I. Jane, A. McKinnon, J. Chromatogr. 323, 191 (1985).

Chemical structure

Derivative

Hydrochloride.
C20H25NO3.HCl; mol wt 363.88.
C 66.01%, H 7.20%, N 3.85%, O 13.19%, Cl 9.74%.

Properties

Long needles, mp 170-172°. Sol in water and alcohols; only slightly sol in chloroform and acetone. Insol in ether, ethyl acetate, benzene. pH (2% aq soln) 4.0-5.5. LD50 i.v. in rats: 66 mg/kg (Yakhontov).

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.