Chemistry:Dimenoxadol
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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,[1] and produces similar effects to other opioids, including analgesia, sedation, dizziness and nausea.[2][3][4]
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:[5] (according to:[6]) Ref:[7][8] Patent:[9] Cmp#3:[10]
- 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.[11]
References
- ↑ Boehringer A, et al., "A new and improved analgesic and process for its production", GB patent 716700, published 10/13/1954
- ↑ "[The pharmacology of estocin, an new analgesic]". Stomatologiia 46 (2): 22–5. 1967. PMID 5232927.
- ↑ "[Pharmacology of dimethylaminoethyl ester of diphenylethoxyacetic acid hydrochloride--estocin]". Farmakologiia i Toksikologiia 32 (6): 710–2. 1969. PMID 5381602.
- ↑ "[Analgesic action of estocin (dimethylaminoethyl ester hydrochloride of alpha, alpha-diphenylethoxyacetic acid)]". Farmakologiia i Toksikologiia 31 (6): 668–71. 1968. PMID 5729519.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Albert Boehringer; Ernst Boehringer; Ilse Liebrecht; Julius Liebrecht +, GB716700 (10/13/1954).
- ↑ Michael Dr. Heschel, et al. EP0537608 (1996 to Apogepha Arzneimittel GmbH).
- ↑ 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.
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