α-Pyrrolidinohexiophenone

α-Pyrrolidinohexiophenone
Clinical data
Routes of
administration		Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous
Legal status
Legal status
Identifiers
  • (RS)-1-Phenyl-2-(pyrrolidin-1-yl)hexan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)
  • C1(=CC=CC=C1)C(C(CCCC)N2CCCC2)=O
  • 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

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[2] which has been reported as a novel designer drug.[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]

Pharmacology

Pharmacological Receptor Activity Profile of Novel Pyrovalerones Compared to Reference Amphetamines [11]
Drug NET DAT SERT DAT/SERT Ratio
⍺-PVP 0.02 (0.01‒0.05) 0.03 (0.02‒0.04) 279 (209‒372) >1000
⍺-PHP 0.06 (0.03‒0.12) 0.06 (0.05‒0.08) 245 (173‒348) >1000
MDMA 0.41 (0.33‒0.52) 13 (11‒16) 1.6 (1.2‒2.2) 0.12 (0.08‒0.20)
Amphetamine 0.07 (0.05‒0.1) 1.3 (0.8‒2.0) 45 (24‒85) 35 (12‒106)

Legality

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

In the US, a-PHP is a Schedule I controlled substance as of 2022.[18]

See also

References

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ US patent 3314970, Ernst Seeger, "α-Pyrrolidino ketones", published 1967-04-18, issued 1967-04-18, assigned to Boehringer Lagelheim G.m.b.H. 
  3. ^ Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (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.
  4. ^ 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.
  5. ^ 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.
  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 M, Kaufmann C, Schwelm HM, Neukamm MA (March 2023). "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. doi:10.1093/jat/bkac057. 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. ^ "The Pharmacological Profile of Second Generation Pyrovalerone Cathinones and Related Cathinone Derivative". nih.gov. PubMed Central. Retrieved 22 February 2026.
  12. ^ "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.
  13. ^ "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.
  14. ^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Archived from the original on 1 July 2015. Retrieved 29 June 2015.
  15. ^ "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.
  16. ^ "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". Archived from the original on 2020-09-26. Retrieved 2021-05-31.
  17. ^ "Verdrag inzake psychotrope stoffen". Tractatenblad van het Koninkrijk der Nederlanden. 77 (7). 21 February 1971. Archived from the original on 2021-09-28. Retrieved 2021-10-29.
  18. ^ Milgram, Anne (June 2022). "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". Federal Register. Drug Enforcement Administration. Retrieved 2024-04-23.
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