Alpha-Pyrrolidinohexiophenone Explained

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[1] which has been reported as a novel designer drug.[2] [3] [4] [5] [6] [7]

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[8]) 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.[9]

Pyrovalerone is a structural isomer of alpha-PHP.[10]

Legality

a-PHP is a Schedule I controlled substance as of 2022.[11]

The President of the Republic of Italy classified cathinone and all structurally derived analogues (including pyrovalerone analogues) as narcotics in January 2012.[12] [13]

Sweden's public health agency suggested to classify α-PHP as narcotic on June 1, 2015.[14]

As of October 2015, α-PHP is a controlled substance in China.[15]

In December 2019, the UNODC announced scheduling recommendations placing Alpha-PHP into Schedule II.[16]

As of October 29, 2021, α-PHP has been banned in the Netherlands under the 1971 Vienna Convention on Psychotropic Substances.[17]

See also

Notes and References

  1. Web site: US Patent 3314970 - α-Pyrrolidino ketones . Ernst Seeger . 18 June 2015 . 19 June 2015 . https://web.archive.org/web/20150619081326/https://www.google.com/patents/US3314970 . live .
  2. Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T . 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 . Forensic Toxicology . August 2014 . 32 . 2 . 266–281 . 10.1007/s11419-014-0238-5. 11873421 .
  3. Majchrzak M, Rojkiewicz M, Celiński R, Kuś P, Sajewicz M . Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials . Forensic Toxicology . 34 . 115–124 . October 2015 . 26793278 . 4705138 . 10.1007/s11419-015-0295-4 .
  4. Paul M, Bleicher S, Guber S, Ippisch J, Polettini A, Schultis W . 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 of Mass Spectrometry . 50 . 11 . 1305–1317 . November 2015 . 26505776 . 10.1002/jms.3642 . 2015JMSp...50.1305P .
  5. Web site: α-Pyrrolidinohexanophenone . Cayman Chemical . 17 June 2015 . 27 May 2015 . https://web.archive.org/web/20150527210012/https://www.caymanchem.com/app/template/Product.vm/catalog/9001934 . live .
  6. Klavž J, Gorenjak M, Marinšek M . 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 . Forensic Science International . 265 . 121–124 . August 2016 . 26890319 . 10.1016/j.forsciint.2016.01.018 .
  7. Grapp M, Kaufmann C, Schwelm HM, Neukamm MA . 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 of Analytical Toxicology . 47 . 2 . 162–174 . March 2023 . 35921233 . 10.1093/jat/bkac057 .
  8. Web site: NIDA IRP - Michael Baumann, Ph.D. . 2018-12-25 . 2018-12-26 . https://web.archive.org/web/20181226035226/https://irp.drugabuse.gov/staff-members/michael-baumann/ . live .
  9. Web site: Wise J . 30 September 2016 . New York Magazine . The Obscure, Legal Drug That Fuels John McAfee . https://web.archive.org/web/20210121184711/https://nymag.com/intelligencer/2016/09/the-obscure-legal-drug-that-fuels-john-mcafee.html . 2021-01-21 .
  10. Meltzer PC, Butler D, Deschamps JR, Madras BK . 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 . 1420–1432 . February 2006 . 16480278 . 2602954 . 10.1021/jm050797a .
  11. Web site: Milgram . Anne . 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 . 2024-04-23 . . Drug Enforcement Administration.
  12. Web site: Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012) . https://web.archive.org/web/20160701171219/http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf . 2016-07-01 . dead.
  13. Web site: EMCDDA–Europol Joint Report on a new psychoactive substance: 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone (α-PVP) . European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) . September 2015 . 2016-05-28 . 2016-06-05 . https://web.archive.org/web/20160605030257/http://www.emcdda.europa.eu/publications/joint-reports/alpha-pvp . live .
  14. Web site: 23 nya ämnen kan klassas som narkotika eller hälsofarlig vara . 29 June 2015 . 1 July 2015 . 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/ . live .
  15. Web site: 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 . China Food and Drug Administration . 27 September 2015 . zh . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 2015-10-01 . dead.
  16. Web site: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling. 2021-05-31. 2020-09-26. https://web.archive.org/web/20200926194857/https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3. live.
  17. Verdrag inzake psychotrope stoffen . Tractatenblad van het Koninkrijk der Nederlanden . 77 . 21 February 1971 . 7 . 2021-10-29. 2021-09-28. https://web.archive.org/web/20210928115959/https://zoek.officielebekendmakingen.nl/trb-2021-110.html. live.

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