alpha-Pyrrolidinohexiophenone

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]

alpha-Pyrrolidinohexiophenone
Clinical data
Routes of
administration		Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II
  • Illegal in China, Sweden and Italy
Identifiers
IUPAC name
  • (RS)-1-Phenyl-2-(pyrrolidin-1-yl)hexan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
SMILES
  • C1(=CC=CC=C1)C(C(CCCC)N2CCCC2)=O
InChI
  • InChI=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
  • Key:KYIJLDDXQWBNGX-UHFFFAOYSA-N

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
  1. "US Patent 3314970 - α-Pyrrolidino ketones". Ernst Seeger. Archived from the original on 19 June 2015. Retrieved 18 June 2015.
  2. Nahoko Uchiyama; Yoshihiko Shimokawa; Maiko Kawamura; Ruri Kikura-Hanajiri; Takashi Hakamatsuka (August 2014). "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. doi:10.1007/s11419-014-0238-5. S2CID 11873421.
  3. Majchrzak M, Rojkiewicz M, Celiński R, Kuś P, Sajewicz M (October 2015). "Identification and characterization of new designer drug 4-fluoro-PV9 and α-PHP in the seized materials". Forensic Toxicology. 34: 115–124. doi:10.1007/s11419-015-0295-4. PMC 4705138. PMID 26793278.
  4. Paul M, Bleicher S, Guber S, Ippisch J, Polettini A, Schultis W (November 2015). "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. Bibcode:2015JMSp...50.1305P. doi:10.1002/jms.3642. PMID 26505776.
  5. "α-Pyrrolidinohexanophenone". Cayman Chemical. Archived from the original on 27 May 2015. Retrieved 17 June 2015.
  6. Klavž J, Gorenjak M, Marinšek M (August 2016). "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. doi:10.1016/j.forsciint.2016.01.018. PMID 26890319.
  7. Grapp, Marcel; Kaufmann, Christoph; Schwelm, Hannes M.; Neukamm, Merja A. (August 2022). "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. doi:10.1093/jat/bkac057. ISSN 1945-2403. PMID 35921233.
  8. "NIDA IRP - Michael Baumann, Ph.D." Archived from the original on 2018-12-26. Retrieved 2018-12-25.
  9. Wise J (30 September 2016). "The Obscure, Legal Drug That Fuels John McAfee". New York Magazine. Archived from the original on 2021-01-21.
  10. 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): 1420–1432. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.
  11. "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. Archived from the original on 2021-04-30. Retrieved 2021-05-31.
  12. "21 U.S. Code § 813 - Treatment of controlled substance analogues".
  13. "Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012)" (PDF). Archived from the original (PDF) on 2016-07-01.
  14. "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. Archived from the original on 2016-06-05. Retrieved 2016-05-28.
  15. "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Archived from the original on 1 July 2015. Retrieved 29 June 2015.
  16. "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 Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 2015-10-01.
  17. "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". Archived from the original on 2020-09-26. Retrieved 2021-05-31.
  18. "Verdrag inzake psychotrope stoffen". Tractatenblad van Het Koninkrijk der Nederlanden. 77 (7). 21 February 1971. Archived from the original on 2021-10-29. Retrieved 2021-10-29.
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