4-ANPP

4-ANPP, also known as 4-anilino-N-phenethylpiperidine (4-ANPP), 4-aminophenyl-1-phenethylpiperidine, or despropionyl fentanyl,[2] is a direct precursor to fentanyl and some fentanyl analogues such as 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.[3] It is not psychoactive and is present only as a result of improper processing of the intended product of the synthesis.

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
3D model (JSmol)
Abbreviations ANPP
ChemSpider
ECHA InfoCard 100.169.974
EC Number
  • 642-161-5
UNII
  • 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,11-16H2
    Key: ZCMDXDQUYIWEKB-UHFFFAOYSA-N
  • C1CN(CCC1NC2=CC=CC=C2)CCC3=CC=CC=C3
Properties
C19H24N2
Molar mass 280.415 g·mol−1
Legal status
  • AU: S9 (Prohibited substance)
  • UK: Scheduled Precursor
  • US: Scheduled Precursor
  • UN: International Red List[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

4-ANPP can be prepared from N-phenethyl-4-piperidinone (NPP) and aniline, then being reduced.

4-ANPP can also be prepared using 4-anilinopiperidine and selectively adding the phenethyl group.

Uses

4-ANPP is useful in the synthesis of pharmaceuticals, primarily fentanyl and its analogs. Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 using 4-ANPP as an intermediate.[4] Janssen's synthesis involved reacting N-phenethyl-4-piperidinone (NPP) with aniline, and then reducing the imine product with sodium borohydride to 4-ANPP. This product is reacted with propionyl chloride to form fentanyl.

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