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.[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).

Norpipanone
Clinical data
Other namesHerchst 10495, NIH-7557
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
  • 4,4-diphenyl-6-(1-piperidinyl)-3-hexanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.008.383
Chemical and physical data
FormulaC23H29NO
Molar mass335.491 g·mol−1
3D model (JSmol)
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:[3][4]

See also

References
  1. Buckingham JB (December 1995). Dictionary of Organic Compounds. CRC Press. p. 2883. ISBN 978-0-412-54090-5. Retrieved 11 May 2012.
  2. 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.
  3. Duprè 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.
  4. 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.
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