Norpipanone

Norpipanone

Clinical data
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
IUPAC name 4,4-diphenyl-6-(1-piperidinyl)-3-hexanone
Synonyms	Herchst 10495, NIH-7557
CAS Number	561-48-8
PubChem (CID)	22391
ChemSpider	21015
UNII	127X8DJ74M
ECHA InfoCard	100.008.383
Chemical and physical data
Formula	C23H29NO
Molar mass	335.483 g/mol
3D model (Jmol)	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

Norpipanone (INN, BAN; Hexalgon) is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries.^[1][2] 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.^[1][2] 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).

Synthesis

Norpipanone synthesis:^[3][4]

See also

• Dipipanone
• Normethadone
• Valeronitrile

References

1. John B Buckingham (December 1995). Dictionary of Organic Compounds. CRC Press. p. 2883. ISBN 978-0-412-54090-5. Retrieved 11 May 2012.
2. David S. Patterson (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.
3. Duprè, D. J.; Elks, J.; Hems, B. A.; Speyer, K. N.; Evans, R. M. (1949). "113. Analgesics. Part I. Esters and ketones derived from α-amino-ω-cyano-ωωdiarylalkanes". Journal of the Chemical Society (Resumed). Chemical Society: 500. doi:10.1039/JR9490000500.
4. Bockmühl, M.; Ehrhart, G. (1949). "Über eine neue Klasse von spasmolytisch und analgetisch wirkenden Verbindungen, I". Justus Liebigs Annalen der Chemie. 561: 52. doi:10.1002/jlac.19495610107.