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4-ANPP

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(Redirected from 4-anilino-N-phenethylpiperidine)
4-ANPP
Names
Preferred IUPAC name N-Phenyl-1-(2-phenylethyl)piperidin-4-amine
Other names desproprionyl fentanyl; 4-anilino-N-phenethylpiperidine; 4-ANPP; ANPP
Identifiers
CAS Number
3D model (JSmol)
Abbreviations ANPP
ChemSpider
ECHA InfoCard 100.169.974 Edit this at Wikidata
EC Number
  • 642-161-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H24N2/c1-3-7-17(8-4-1)11-14-21-15-12-19(13-16-21)20-18-9-5-2-6-10-18/h1-10,19-20H,11-16H2Key: ZCMDXDQUYIWEKB-UHFFFAOYSA-N
SMILES
  • C1CN(CCC1NC2=CC=CC=C2)CCC3=CC=CC=C3
Properties
Chemical formula C19H24N2
Molar mass 280.415 g·mol
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class D1 (Drug precursors)
  • UK: Scheduled Precursor
  • US: Schedule II
  • UN: International Red List
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

4-ANPP, also known as 4-anilino-N-phenethylpiperidine (4-ANPP), 4-aminophenyl-1-phenethylpiperidine, or despropionyl fentanyl, is a direct precursor to fentanyl and acetylfentanyl. It is commonly found as a contaminant in samples of drugs containing fentanyl, which may include samples represented by the supplier as heroin or other opioids. It is not psychoactive and is present only as a result of improper chemical purification.

4-ANPP is useful in the synthesis of pharmaceuticals, primarily fentanyl and related analogs. Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 using a similar method, with Benzylfentanyl as an intermediate. The following synthesis, developed by an individual under the pseudonym of Siegfried, involves the reductive amination of N-phenethyl-4-piperidinone (NPP) with aniline to make to 4-ANPP. This product is reacted with propionyl chloride or acetyl chloride to form either fentanyl or acetylfentanyl.

See also

References

  1. "Red list". www.incb.org. Retrieved 2021-02-20.
  2. 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 2023-08-15.
  3. "4-ANPP". www.caymanchem.com. Retrieved 2021-02-19.
  4. DrugsData.org. "DrugsData.org: Results : Lab Test Results for Fentanyl". www.drugsdata.org. Retrieved 2021-02-19.
  5. Schulz W. "Fentanyl". List of Top Pharmaceuticals. Chemical & Engineering News.
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