Propoxyphene hydrochloride

Hiltmann, R., Wollweber, H., Hoffmeister, F., Wirth, W. and Kroneberg, H.-G. U.S. Patent 3,163,654 December 29, 1964 assigned to Farbenfabriken Bayer AG, Germany Wollweber, H., Hiltmann, R., Hoffmeister, F. and Kroneberg, H.-G. U.S. Patent 3,594,477 July 20, 1971 assigned to Farbenfabriken Bayer AG, Germany 

Chemical Name (S)-a-[2-(dimethylamino)-1-methylethyl] -a-phenylbenzeneethanol pro-panoate hydrochloride 

Common Name Dextropropoxyphene hydrochloride Structural Formula  

Trade Name Manufacturer Country Year Introduced 

Dry hydrogen chloride gas was passed into the ether solution until precipitation was completed. The solid was removed by filtration and was recrystallized from a mixture of methanol and ethyl acetate. The a-dl-1,2-diphenyl-2-hydroxy-3-methyl-4-dimethylamino-butane hydrochloride thus obtained melted at about 231° to 232°C. 

Chemical Name (S)-Q -[2-(dlmethylamino)-1 -methylethyl] -a jhenylbenzeneethanol pro-panoate hydrochloride 

A mixture of 50 grams of a-dl-1,2-diphenyl-2-hydroxy-3-methyl-4-dimethylaminobutane hydrochloride, 50 grams of propionic anhydride and 50 cc of pyridine was refluxed for about 5 hours. The reaction mixture was cooled to 50°C and ethyl ether was added to the point of incipient precipitation. The hydrochloride salt of 0 -dl-l,2-diphenyl-2-propion-oxy-3-methyl-4-dimethylamlnobutane formed in the reaction precipitated upon cooling and was removed by filtration and washed with anhydrous ether. On recrystallization from a mixture of methanol and ethyl acetate, a-dl-l, 2-diphenyl-2-propionoxy-3-methyl-4-dimethyl amlnobutane hydrochloride melted at 170°-171°C. 

Pohland, A. U.S. Patent 2,728,779 December 27, 1955 assigned to Eli Lilly and Company 

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Medium to low abuse potential with possible medical value in U.S. Tranquilizers, phenobarbital, propoxyphene hydrochloride (Darvon)... 

Warning - See Warning Box at the beginning of the monograph. Propoxyphene hydrochloride -... 

Mild to moderate pain PO (propoxyphene hydrochloride) 65 mg q4h as needed. Maximum 390mg/day. PO (propoxyphene napsylate) 100 mg q4h as needed. Maximum 600 mg/day. 

Diphenylpropylamine derivatives propoxyphene hydrochloride propoxyphene napsylate... 

Some compounds that affect respiratory rate. Acetaminophen is one of the simple analgesics, which in therapeutic doses relieves pain without any effect on an individual s consciousness. Propoxyphene hydrochloride is a narcotic analgesic, a class of substances that can cause biochemical changes in the body leading to chemical dependency. 

S. Kryger and P. Helboe, Determination of impurities in dextro-propoxyphene hydrochloride by HPLC on dynamically modified silica, J. Chromatogr., 559 186 (1991). 

Darvon , d-propoxyphene hydrochloride, is a synthetic, nonantipyritic, orally effective analgesic, with similar pharmacological activity and effects to codeine. Darvon is not a narcotic but can be substituted for codeine, and is useful in any condition associated with pain. Chemically, this analgesic is not analogous to codeine or to morphine. 

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