Phenadoxone

Phenadoxone (trade names Heptalgin, Morphidone, and Heptazone) is an opioid analgesic[1][2] of the open chain class (methadone and relatives) invented in Germany by Hoechst in 1947.[3][4] 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United States for various lengths of time in the 20 or so years after the end of the Second World War but which were withdrawn from the market for various or no known reason and which now are mostly in Schedule I of the United States' Controlled Substances Act of 1970, or (like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).

Phenadoxone
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
Identifiers
IUPAC name
  • 6-Morpholin-4-yl-4,4-diphenylheptan-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.006.729
Chemical and physical data
FormulaC23H29NO2
Molar mass351.490 g·mol−1
3D model (JSmol)
Melting point75.5 °C (167.9 °F)
SMILES
  • O=C(C(c1ccccc1)(c2ccccc2)CC(N3CCOCC3)C)CC
InChI
  • InChI=1S/C23H29NO2/c1-3-22(25)23(20-10-6-4-7-11-20,21-12-8-5-9-13-21)18-19(2)24-14-16-26-17-15-24/h4-13,19H,3,14-18H2,1-2H3 Y
  • Key:LOXCOAXRHYDLOW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Phenadoxone has a US DEA ACSCN of 9637 and recently has had a zero annual manufacturing quota under the Controlled Substances Act 1970.[5] 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.

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.

Worldwide consumption of phenadoxone has actually increased slightly in recent years according to a recent report from the World Health Organization. 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.

References
  1. "Phenadoxone". Merck Index. 2000.
  2. Physicians' Desk Reference. 1965.
  3. US 2513173, Benjamin AR, Elks J, "4,4-diphenyl-6-morpholino-heptanone-3 and acid salts thereof", assigned to Glaxo
  4. Basil B, Edge ND, Somers GF (March 1950). "The pharmacology of phenadoxone or dl-6-morpholino-4:4-diphenyl-heptan-3-one hydrochloride". British Journal of Pharmacology and Chemotherapy. 5 (1): 125–41. doi:10.1111/j.1476-5381.1950.tb00582.x. PMC 1509948. PMID 15405474.
  5. "Quotas - 2013". Diversion Control Division. US Department of Justice, Drug Enforcement Administration.
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