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,[2] and produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.[3][4][5]

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:[6] (according to:[7]) Ref:[8][9] Patent:[10] Cmp#3:[11]

  • 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.[12]

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ↑ GB 716700, Boehringer A, et al., "A new and improved analgesic and process for its production", published 10/13/1954
  3. ↑ Gorbatova EN (1967). "[The pharmacology of estocin, an new analgesic]". Stomatologiia. 46 (2): 22–5. PMID 5232927.
  4. ↑ Kingisepp GI, Kurvits K, Nurmand LB (1969). "[Pharmacology of dimethylaminoethyl ester of diphenylethoxyacetic acid hydrochloride--estocin]". Farmakologiia i Toksikologiia. 32 (6): 710–2. PMID 5381602.
  5. ↑ Liberman SS (1968). "[Analgesic action of estocin (dimethylaminoethyl ester hydrochloride of alpha, alpha-diphenylethoxyacetic acid)]". Farmakologiia i Toksikologiia. 31 (6): 668–71. PMID 5729519.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ Yakhontov, L.N. et al, Khim.-Farm. Zh., 1974, 8, 56.
  10. ↑ Albert Boehringer; Ernst Boehringer; Ilse Liebrecht; Julius Liebrecht +, GB716700 (10/13/1954).
  11. ↑ Michael Dr. Heschel, et al. EP0537608 (1996 to Apogepha Arzneimittel GmbH).
  12. ↑ 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.
source: https://en.wikipedia.org/wiki/Dimenoxadol