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Compound

Phenadoxone

Also called Phenodoxone, Heptazone, Fenadossone

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Overview

Phenadoxone (trade names Heptalgin, Morphidone, and Heptazone) is an opioid analgesic of the open chain class (methadone and relatives) invented in Germany by Hoechst in 1947. It is one of a handful of useful synthetic analgesics which were used in the United States for various lengths of time in the 20 or so years after the end of the Second World War but which were withdrawn from the market for various or no known reason and which now are mostly in Schedule I of the United States' Controlled Substances Act of 1970, or (like phenazocine and bezitramide) in Schedule II but not produced or marketed in the US. Others on this list are ketobemidone (Ketogin), dextromoramide (Dimorlin, Palfium and others), phenazocine (Narphen and Prinadol), dipipanone (Diconal, Pipadone and Wellconal), piminodine (Alvodine), propiram (Algeril), anileridine (Leritine) and alphaprodine (Nisentil).[1–4] WP

Phenadoxone has a US DEA ACSCN of 9637 and has had a zero annual manufacturing quota under the Controlled Substances Act 1970. Its withdrawal from US distribution prior to the promulgation of said act is a large part of its Schedule I designation; it is, however, used as a legitimate medication in other countries and consumption is increasing worldwide as indicated below.[5] WP

Phenadoxone is generally considered to be a strong opioid analgesic and is regulated in much the same way as morphine where it is used. The usual starting dose is 10–20 mg and it has a duration of analgesic effect of 1 to 4 hours. Phenadoxone is not used at this time for purposes other than pain relief. WP

Like its drug subcategory prototype methadone, phenadoxone can be used as the opioid analgesic in Brompton cocktail. Phenadoxone is most used at the current time in Denmark and various countries in eastern Europe. WP

Chemistry

Formula
C23H29NO2 PC
CAS number
467-84-5 PC
Molar mass (g/mol)
351.5 PC
IUPAC name (computed by PubChem)
6-morpholin-4-yl-4,4-diphenylheptan-3-one PC
SMILES
CCC(=O)C(CC(C)N1CCOCC1)(C2=CC=CC=C2)C3=CC=CC=C3 PC
InChIKey
LOXCOAXRHYDLOW-UHFFFAOYSA-N PC
PubChem CID
10089

Harm reduction information

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Sources

  1. Other Merck Index. 2000
  2. Other Physicians' Desk Reference. 1965
  3. Other 4,4-diphenyl-6-morpholino-heptanone-3 and acid salts thereof
  4. Journal / agency Basil B, Edge ND, Somers GF. The pharmacology of phenadoxone or dl-6-morpholino-4:4-diphenyl-heptan-3-one hydrochloride. British Journal of Pharmacology and Chemotherapy. March 1950. doi:10.1111/j.1476-5381.1950.tb00582.x · PMID 15405474 · PMC1509948
  5. Other Quotas - 2013

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.