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Α-PHiP





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α-Pyrrolidinoisohexanophenone (mainly known as A-PiHPorα-PiHP) is a stimulant drug of the cathinone class that has been sold online as a designer drug. It is a positional isomerofpyrovalerone, 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.[2] α-PiHP acts as a norepinephrine–dopamine reuptake inhibitor. Compared to α-PVP and α-PHP, α-PiHP displays a higher selectivity for the dopamine transporter. Similar to other cathinones, use of α-PiHP can result in compulsive redosing, addiction, anxiety, paranoia, and psychosis. In July 2016 α-PHiP was first identified as a designer drug[3] when it was reported to the EMCDDA by a forensic laboratory in Slovenia.[4][5]

α-Pyrrolidinoisohexanophenone
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • Identifiers
    • 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one

    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC16H23NO
    Molar mass245.366 g·mol−1
    3D model (JSmol)
    • CC(C)CC(C(=O)c1ccccc1)N2CCCC2

    • 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

    edit

    References

    edit
    1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  • ^ 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.
  • ^ "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.
  • ^ "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.
  • ^ 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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    Last edited on 23 June 2024, at 03:51  





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    This page was last edited on 23 June 2024, at 03:51 (UTC).

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