Norpipanone

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
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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

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

References

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