Phenadoxone

Phenadoxone (trade names Heptalgin, Morphidone, and Heptazone) is an opioid analgesic^[2][3] of the open chain class (methadone and relatives) invented in Germany by Hoechst in 1947.^[4][5] 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United States for various lengths of time in the 20 or so years after the end of the Second World War but which were withdrawn from the market for various or no known reason and which now are mostly in Schedule I of the United States' Controlled Substances Act of 1970, or (like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) BR: Class A1 (Narcotic drugs)[1] 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	467-84-5 N
PubChem CID	10089
ChemSpider	9686 Y
UNII	375W3TA42N
KEGG	D12698 Y
CompTox Dashboard (EPA)	DTXSID70861963
ECHA InfoCard	100.006.729
Chemical and physical data
Formula	C23H29NO2
Molar mass	351.490 g·mol−1
3D model (JSmol)	Interactive image
Melting point	75.5 °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 has had a zero annual manufacturing quota under the Controlled Substances Act 1970.^[6] 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.

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. 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. "Phenadoxone". Merck Index. 2000.
3. Physicians' Desk Reference. 1965.
4. US 2513173, Benjamin AR, Elks J, "4,4-diphenyl-6-morpholino-heptanone-3 and acid salts thereof", assigned to Glaxo
5. 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.
6. "Quotas - 2013". Diversion Control Division. US Department of Justice, Drug Enforcement Administration.