Chemistry:Alpha-Pyrrolidinohexiophenone
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| Routes of administration | Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous |
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| Formula | C16H23NO |
| Molar mass | 245.366 g·mol−1 |
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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
In the United States, α-PHP in the past has been assigned to Schedule I on a Temporary Placement basis, although the order has expired without renewal or permanent placement and is no longer Scheduled at the Federal level as of July 2021.[11] Despite this however, α-PHP may be considered an analogue of α-PVP, a Schedule I drug under the Controlled Substances Act. As such, possession or the sale for human consumption or the use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes under the Federal Analogue Act.[12]
The President of the Republic of Italy classified cathinone and all structurally derived analogues (including pyrovalerone analogues) as narcotics in January 2012.[13][14]
Sweden's public health agency suggested to classify α-PHP as narcotic on June 1, 2015.[15]
As of October 2015, α-PHP is a controlled substance in China.[16]
In December 2019, the UNODC announced scheduling recommendations placing Alpha-PHP into Schedule II.[17]
As of October 29, 2021, α-PHP has been banned in the Netherlands under the 1971 Vienna Convention on Psychotropic Substances.[18]
See also
References
- ↑ "US Patent 3314970 - α-Pyrrolidino ketones". Ernst Seeger. https://www.google.com/patents/US3314970.
- ↑ "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 32 (2): 266–281. August 2014. doi:10.1007/s11419-014-0238-5.
- ↑ "Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials". Forensic Toxicology 34: 115–124. October 2015. doi:10.1007/s11419-015-0295-4. PMID 26793278.
- ↑ "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. doi:10.1002/jms.3642. PMID 26505776. Bibcode: 2015JMSp...50.1305P.
- ↑ "α-Pyrrolidinohexanophenone". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/9001934.
- ↑ "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. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.
- ↑ "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. doi:10.1093/jat/bkac057. PMID 35921233.
- ↑ "NIDA IRP - Michael Baumann, Ph.D.". https://irp.drugabuse.gov/staff-members/michael-baumann/.
- ↑ "The Obscure, Legal Drug That Fuels John McAfee". New York Magazine. 30 September 2016. https://nymag.com/intelligencer/2016/09/the-obscure-legal-drug-that-fuels-john-mcafee.html.
- ↑ "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. doi:10.1021/jm050797a. PMID 16480278.
- ↑ "Schedules of Controlled Substances: Temporary Placement of N-Ethylhexedrone, α-PHP, 4-MEAP, MPHP, PV8, and 4-Chloro-α-PVP in Schedule I". Drug Enforcement Administration. https://www.deadiversion.usdoj.gov/fed_regs/rules/2019/fr0501.htm.
- ↑ "21 U.S. Code § 813 - Treatment of controlled substance analogues". https://www.law.cornell.edu/uscode/text/21/813.
- ↑ "Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012)". http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf.
- ↑ "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. http://www.emcdda.europa.eu/publications/joint-reports/alpha-pvp.
- ↑ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/juni/23-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara.
- ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html.
- ↑ "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3.
- ↑ "Verdrag inzake psychotrope stoffen". Tractatenblad van het Koninkrijk der Nederlanden 77 (7). 21 February 1971. https://zoek.officielebekendmakingen.nl/trb-2021-110.html#d17e4724. Retrieved 2021-10-29.
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