Α-PHiP

{{Short description|Stimulant drug}}

{{lowercase title}}

{{Drugbox

| drug_name = α-Pyrrolidinoisohexanophenone

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| IUPAC_name = 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one

| image = Alpha-PHiP structure.png

| tradename =

| pregnancy_category =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule I

| legal_DE = Anlage II

| legal_UK = Class B

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref =

| CAS_number = 2181620-71-1

| ATC_prefix =

| ATC_suffix =

| PubChem = 59809191

| KEGG = C22829

| ChemSpiderID = 68006957

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9AF2IHV9HK

| ChEMBL =

| DTXSID =

| C = 16

| H = 23

| N = 1

| O = 1

| melting_point =

| smiles = CC(C)CC(C(=O)c1ccccc1)N2CCCC2

| StdInChI = 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

| StdInChIKey = UOZWZANRCOALQL-UHFFFAOYSA-N

}}

α-Pyrrolidinoisohexanophenone (mainly known as A-PiHP or α-PiHP) is a stimulant drug of the cathinone class that has been sold online as a designer drug. It acts as a potent norepinephrine-dopamine reuptake inhibitor (NDRI). In July 2016 α-PiHP was first identified as a designer drug{{cite web |date=July 2016 |title=Analytic Report alpha-PHiP (C16H23NO) 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one. |url=https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/alpha-PHiP-ID-1723-16rpt071216.pdf |url-status=live |archive-url=https://web.archive.org/web/20201003004736/https://www.policija.si/apps/nfl_response_web/0_Analytical_Reports_final/alpha-PHiP-ID-1723-16rpt071216.pdf |archive-date=2020-10-03 |access-date=2019-10-24 |publisher=Nacionalni forenzični laboratorij |location=Slovenia}} when it was reported to the EMCDDA by a forensic laboratory in Slovenia.{{cite journal |title=Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA |url=http://www.emcdda.europa.eu/system/files/publications/4724/TDAN17001ENN_PDFWEB.pdf |url-status=live |journal=EMCDDA–Europol Joint Publication |archive-url=https://web.archive.org/web/20210126100454/https://www.emcdda.europa.eu/system/files/publications/4724/TDAN17001ENN_PDFWEB.pdf |archive-date=2021-01-26 |access-date=2019-10-24}}{{cite journal |vauthors=Liu C, Jia W, Li T, Hua Z, Qian Z |date=August 2017 |title=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 |journal=Drug Testing and Analysis |volume=9 |issue=8 |pages=1162–1171 |doi=10.1002/dta.2136 |pmid=27863142}} 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. Similarly to other cathinones, use of α-PiHP can result in compulsive redosing, addiction, anxiety, paranoia, and psychosis.