Dimenoxadol (INN; also known as dimenoxadole (BAN) or dimenoxadole; brand name Estocin in Russia) is an opioid analgesic which is a benzilic acid derivative, closely related to benactyzine (an anticholinergic). Further, the structure is similar to methadone and related compounds like dextropropoxyphene.
It was invented in Germany in the 1950s, and produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.
In the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9617 and a 2013 annual aggregate manufacturing quota of zero. Synthesis The chemical synthesis has been reported:Doyle, F. P.; Mehta, M. D.; Ward, R.; Bainbridge, J.; Brown, D. M. (1965). "Chemistry and Pharmacology of Some Esters Derived from Basic Alcohols". Journal of Medicinal Chemistry. 8 (5): 571–576. doi:10.1021/jm00329a005. (according to:Doyle, F. P.; Mehta, M. D.; Sach, G. S.; Ward, R.; Sherman, P. S. (1964). "116. Pharmacodynamic compounds. Part III. Antitussives derived from 1-alkylpyrrolidinyl and 1-alkylpiperidyl alcohols". Journal of the Chemical Society (Resumed): 578. doi:10.1039/jr9640000578.) Ref:Klosa, Josef (1955). "Synthese einiger α,α-Diphenyl-α-alkoxy-essigsäure-(β-dimethylaminoäthyl)-ester. 9. Mitteilung über Synthese spasmolytischer Körper". Archiv der Pharmazie. 288 (1): 42–47. doi:10.1002/ardp.19552880109.Yakhontov, L.N. et al, Khim.-Farm. Zh., 1974, 8, 56. Patent:Albert Boehringer; Ernst Boehringer; Ilse Liebrecht; Julius Liebrecht +, GB716700 (10/13/1954). Cmp#3:Michael Dr. Heschel, et al. EP0537608 (1996 to Apogepha Arzneimittel GmbH).
The reaction between 2-chloro-2,2-diphenylacetyl chloride [2902-98-9] (1) and Deanol [108-01-0] (2) gives [3042-75-9] (3). The intermediate haloalkane is then alkoxylated by refluxing in ethanol, completing the synthesis of Dimenoxadol (4). The 2-chloro-2,2-diphenylacetyl chloride is made by reacting benzilic acid with phosphorus pentachloride.Stevens, Calvin L.; French, James C. (1953). "Nitrogen Analogs of Ketenes. A New Method of Preparation1". Journal of the American Chemical Society. 75 (3): 657–660. doi:10.1021/ja01099a043.
References