| |
| |
| 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 |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C19H24N2 | |
| Molar mass | 280.415 g·mol−1 |
| Legal status |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
4-ANPP, also known as 4-anilino-N-phenethylpiperidine (4-ANPP), 4-aminophenyl-1-phenethylpiperidine, or despropionyl fentanyl,[3] 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.[4] It is not psychoactive and is present only as a result of improper chemical purification.
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 related analogs. Paul Janssen (founder of Janssen Pharmaceutica) first synthesized fentanyl in 1960 using a similar method, with Benzylfentanyl as an intermediate.[5] The following synthesis, developed by an individual under the pseudonym of Siegfried, involves the reductive amination of N-phenethyl-4-piperidinone (NPP) to 4-ANPP. This product is reacted with propionyl chloride or acetyl chloride to form either fentanyl or acetylfentanyl.
See also
References
- ^ "Red list". www.incb.org. Retrieved 2021-02-20.
- ^ 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.
- ^ "4-ANPP". www.caymanchem.com. Retrieved 2021-02-19.
- ^ DrugsData.org. "DrugsData.org: Results : Lab Test Results for Fentanyl". www.drugsdata.org. Retrieved 2021-02-19.
- ^ Schulz W. "Fentanyl". List of Top Pharmaceuticals. Chemical & Engineering News.
This page was last edited on 7 March 2024, at 01:37