Norpipanone

Norpipanone (INN, BAN; Hexalgon) is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries.^[2][3] It had originally not been under international control but upon observation of case reports of addiction it was reviewed and shortly thereafter became a controlled substance.^[2][3] In the United States, it is a Schedule I controlled substance (ACSCN 9636, zero annual manufacturing quota as of 2014). The salts in use are the hydrobromide (free base conversion ratio 0.806) and hydrochloride (0.902).

Norpipanone

Clinical data
Other names	Herchst 10495, NIH-7557
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 4,4-diphenyl-6-(1-piperidinyl)-3-hexanone
CAS Number	561-48-8
PubChem CID	22391
ChemSpider	21015
UNII	127X8DJ74M
KEGG	D12701 Y
CompTox Dashboard (EPA)	DTXSID60204643
ECHA InfoCard	100.008.383
Chemical and physical data
Formula	C23H29NO
Molar mass	335.491 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(C(c1ccccc1)(c2ccccc2)CCN3CCCCC3)CC
InChI InChI=1S/C23H29NO/c1-2-22(25)23(20-12-6-3-7-13-20,21-14-8-4-9-15-21)16-19-24-17-10-5-11-18-24/h3-4,6-9,12-15H,2,5,10-11,16-19H2,1H3 Key:WCDSHELZWCOTMI-UHFFFAOYSA-N

Synthesis

Norpipanone synthesis:^[4][5]

See also

• Dipipanone
• Normethadone

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. Buckingham JB (December 1995). Dictionary of Organic Compounds. CRC Press. p. 2883. ISBN 978-0-412-54090-5. Retrieved 11 May 2012.
3. Patterson DS (12 March 2002). Foreign Relations of the United States, 1961-1963, Volume XXV: Organization of Foreign Policy; Information Policy; United Nations; Scientific Matters. Government Printing Office. pp. 766–767. ISBN 978-0-16-050885-1. Retrieved 11 May 2012.
4. Dupré DJ, Elks J, Hems BA, Speyer KN, Evans RM (1949). "113. Analgesics. Part I. Esters and ketones derived from α-amino-ω-cyano-ωωdiarylalkanes". Journal of the Chemical Society (Resumed). Chemical Society: 500–510. doi:10.1039/JR9490000500.
5. Bockmühl M, Ehrhart G (1949). "Über eine neue Klasse von spasmolytisch und analgetisch wirkenden Verbindungen, I". Justus Liebigs Annalen der Chemie. 561: 52–86. doi:10.1002/jlac.19495610107.