α-PHiP

α-PHiP (also known as α-PiHP), is a stimulant drug of the cathinone class that has been sold online as a designer drug. It is a positional isomer of pyrovalerone, with the methyl group shifted from the 4-position of the aromatic ring to the 4-position of the acyl chain. In a classic 2006 study of pyrrolidinyl cathinone derivatives by Meltzer et al. at Organix, the alpha-isobutyl derivative of pyrovalerone, O-2494, was found to have the highest potency in vitro as an inhibitor of the dopamine transporter of the alpha substituted derivatives tested,[1] however it was not until ten years later in July 2016 that α-PHiP was first identified as a designer drug,[2] when it was reported to the EMCDDA by a forensic laboratory in Slovenia.[3][4]

α-PHiP
Legal status
Legal status
  • CA: Schedule I
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • US: Schedule I (positional isomer of a-PHP)
Identifiers
IUPAC name
  • 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)CC(C(=O)c1ccccc1)N2CCCC2
InChI
  • InChI=1S/C16H23NO/c1-13(2)12-15(17-10-6-7-11-17)16(18)14-8-4-3-5-9-14/h3-5,8-9,13,15H,6-7,10-12H2,1-2H3
  • Key:UOZWZANRCOALQL-UHFFFAOYSA-N

See also

References
  1. Meltzer PC, Butler D, Deschamps JR, Madras BK (February 2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry. 49 (4): 1420–32. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.
  2. "Analytic Report alpha-PHiP (C16H23NO) 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one" (PDF). Slovenia: Nacionalni forenzični laboratorij. July 2016. Archived (PDF) from the original on 2020-10-03. Retrieved 2019-10-24.
  3. "Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). EMCDDA–Europol Joint Publication. Archived (PDF) from the original on 2021-01-26. Retrieved 2019-10-24.
  4. Liu C, Jia W, Li T, Hua Z, Qian Z (August 2017). "Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP". Drug Testing and Analysis. 9 (8): 1162–1171. doi:10.1002/dta.2136. PMID 27863142.


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