Α-Pyrrolidinohexiophenone
{{Short description|Stimulant drug}}
{{lowercase title}}
{{Drugbox
| Watchedfields =
| verifiedrevid =
| IUPAC_name = (RS)-1-Phenyl-2-(pyrrolidin-1-yl)hexan-1-one
| image = Α-PHP.svg
| image2 = A-PHP23.jpg
| alt2 =
| drug_name = α-Pyrrolidinohexiophenone
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| 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 =
| legal_DE = Anlage II
| legal_UK = Class B
| legal_US = Schedule I
| legal_UN = P II
| legal_status = Illegal in China, Sweden and Italy
| routes_of_administration = Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| index_label =
| index2_label = HCl
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 13415-86-6
| CAS_number2_Ref = {{cascite|correct|CAS}}
| CAS_number2 = 13415-59-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 297J9K8A4G
| ATC_prefix =
| ATC_suffix =
| PubChem = 102107923
| KEGG = C22753
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 52084419
| ChEMBL_Ref =
| ChEMBL =
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = Z5DJ7QN981
| C = 16
| H = 23
| N = 1
| O = 1
| smiles = C1(=CC=CC=C1)C(C(CCCC)N2CCCC2)=O
| StdInChI_Ref =
| StdInChI = 1S/C16H23NO/c1-2-3-11-15(17-12-7-8-13-17)16(18)14-9-5-4-6-10-14/h4-6,9-10,15H,2-3,7-8,11-13H2,1H3
| StdInChIKey_Ref =
| StdInChIKey = KYIJLDDXQWBNGX-UHFFFAOYSA-N
}}
α-Pyrrolidinohexiophenone (α-PHP, A-PHP, Aphp, alpha-PHP, α-Pyrrolidinohexanophenone, PV-7) is a synthetic stimulant drug of the cathinone class developed in the 1960s{{cite patent| country = US| number = 3314970| inventor = Ernst Seeger| status = patent| title = α-Pyrrolidino ketones| pubdate = 1967-04-18| gdate = 1967-04-18| fdate = 1964-10-14| pridate = 1960-04-07| assign1 = Boehringer Lagelheim G.m.b.H.}} which has been reported as a novel designer drug.{{cite journal | vauthors=Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T | title=Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products | journal=Forensic Toxicology | date=August 2014 | volume=32 | issue=2 | pages=266–281 | doi=10.1007/s11419-014-0238-5 | s2cid=11873421}}{{cite journal | vauthors=Majchrzak M, Rojkiewicz M, Celiński R, Kuś P, Sajewicz M | title=Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials | journal=Forensic Toxicology | volume=34 | pages=115–124 | date=October 2015 | pmid=26793278 | pmc=4705138 | doi=10.1007/s11419-015-0295-4}}{{cite journal | vauthors=Paul M, Bleicher S, Guber S, Ippisch J, Polettini A, Schultis W | title=Identification of phase I and II metabolites of the new designer drug α-pyrrolidinohexiophenone (α-PHP) in human urine by liquid chromatography quadrupole time-of-flight mass spectrometry (LC-QTOF-MS) | journal=Journal of Mass Spectrometry | volume=50 | issue=11 | pages=1305–1317 | date=November 2015 | pmid=26505776 | doi=10.1002/jms.3642 | bibcode=2015JMSp...50.1305P}}{{cite journal | vauthors=Klavž J, Gorenjak M, Marinšek M | title=Suicide attempt with a mix of synthetic cannabinoids and synthetic cathinones: Case report of non-fatal intoxication with AB-CHMINACA, AB-FUBINACA, alpha-PHP, alpha-PVP and 4-CMC | journal=Forensic Science International | volume=265 | pages=121–124 | date=August 2016 | pmid=26890319 | doi=10.1016/j.forsciint.2016.01.018}}{{cite journal | vauthors=Grapp M, Kaufmann C, Schwelm HM, Neukamm MA | title=Toxicological Investigation of a Case Series Involving the Synthetic Cathinone α-Pyrrolidinohexiophenone (α-PHP) and Identification of Phase I and II Metabolites in Human Urine | journal=Journal of Analytical Toxicology | volume=47 | issue=2 | pages=162–174 | date=March 2023 | pmid=35921233 | doi=10.1093/jat/bkac057}}
Similar chemical compounds
α-Pyrrolidinohexiophenone is a longer chain homologue of α-PVP, having an extra carbon on the alkyl side chain. Regarding the potency of alpha-PHP in the brain, chemist Michael H. Baumann of the Designer Drug Research Unit (established by Baumann{{Cite web | url=https://irp.drugabuse.gov/staff-members/michael-baumann/ | title=NIDA IRP - Michael Baumann, Ph.D. | access-date=2018-12-25 | archive-date=2018-12-26 | archive-url=https://web.archive.org/web/20181226035226/https://irp.drugabuse.gov/staff-members/michael-baumann/ | url-status=live}}) of the National Institute on Drug Abuse stated: "alpha-PHP might be even more potent than alpha-PVP"; this statement is based on laboratory tests of chemical reactivity.{{cite web | vauthors=Wise J | date=30 September 2016 | work=New York Magazine | title=The Obscure, Legal Drug That Fuels John McAfee | url=https://nymag.com/intelligencer/2016/09/the-obscure-legal-drug-that-fuels-john-mcafee.html | archive-url=https://web.archive.org/web/20210121184711/https://nymag.com/intelligencer/2016/09/the-obscure-legal-drug-that-fuels-john-mcafee.html | archive-date=2021-01-21}}
Pyrovalerone is a structural isomer of alpha-PHP.{{cite journal | vauthors=Meltzer PC, Butler D, Deschamps JR, Madras BK | title=1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors | journal=Journal of Medicinal Chemistry | volume=49 | issue=4 | pages=1420–1432 | date=February 2006 | pmid=16480278 | pmc=2602954 | doi=10.1021/jm050797a}}
Legality
The President of the Republic of Italy classified cathinone and all structurally derived analogues (including pyrovalerone analogues) as narcotics in January 2012.{{Cite web | title=Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012) | url=http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf | archive-url=https://web.archive.org/web/20160701171219/http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf | archive-date=2016-07-01 | url-status=dead}}{{Cite web | title=EMCDDA–Europol Joint Report on a new psychoactive substance: 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone (α-PVP) | url=http://www.emcdda.europa.eu/publications/joint-reports/alpha-pvp | publisher=European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) | date=September 2015 | access-date=2016-05-28 | archive-date=2016-06-05 | archive-url=https://web.archive.org/web/20160605030257/http://www.emcdda.europa.eu/publications/joint-reports/alpha-pvp | url-status=live}}
Sweden's public health agency suggested to classify α-PHP as narcotic on June 1, 2015.{{Cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara | title=23 nya ämnen kan klassas som narkotika eller hälsofarlig vara | access-date=29 June 2015 | archive-date=1 July 2015 | archive-url=https://web.archive.org/web/20150701230025/http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | url-status=live}}
As of October 2015, α-PHP is a controlled substance in China.{{Cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=2015-10-01 | url-status=dead}}
In December 2019, the UNODC announced scheduling recommendations placing Alpha-PHP into Schedule II.{{cite web | url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3 | title=December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling | access-date=2021-05-31 | archive-date=2020-09-26 | archive-url=https://web.archive.org/web/20200926194857/https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3 | url-status=live}}
As of 29 October 2021, α-PHP has been banned in the Netherlands under the 1971 Vienna Convention on Psychotropic Substances.{{cite journal | url=https://zoek.officielebekendmakingen.nl/trb-2021-110.html#d17e4724 | journal=Tractatenblad van het Koninkrijk der Nederlanden | volume=77 | date=21 February 1971 | issue=7 | title=Verdrag inzake psychotrope stoffen | access-date=2021-10-29 | archive-date=2021-09-28 | archive-url=https://web.archive.org/web/20210928115959/https://zoek.officielebekendmakingen.nl/trb-2021-110.html | url-status=live}}
In the US, a-PHP is a Schedule I controlled substance as of 2022.{{Cite web | last=Milgram | first=Anne | date= June 2022| title=Schedules of Controlled Substances: Placement of N-Ethylhexedrone, alpha-Pyrrolidinohexanophenone, 4-Methyl-alpha-ethylaminopentiophenone, 4′-Methyl-alpha-pyrrolidinohexiophenone, alpha-Pyrrolidinoheptaphenone, and 4′-Chloro-alpha-pyrrolidinovalerophenone in Schedule I | url=https://www.federalregister.gov/documents/2022/06/01/2022-11740/schedules-of-controlled-substances-placement-of-n-ethylhexedrone-alpha-pyrrolidinohexanophenone | access-date=2024-04-23 | website=Federal Register | publisher=Drug Enforcement Administration}}
See also
References
{{Reflist}}
{{Stimulants}}
{{Phenethylamines}}
{{DEFAULTSORT:Pyrrolidinohexiophenone, α-}}