Α-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^[2] which has been reported as a novel designer drug.^{[3][4][5][6][7]}

α-Pyrrolidinohexiophenone

Clinical data
Routes of administration	Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] 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	13415-86-6 Y HCl: 13415-59-3 Y
PubChem CID	102107923
ChemSpider	52084419
UNII	297J9K8A4G HCl: Z5DJ7QN981 Y
KEGG	C22753
CompTox Dashboard (EPA)	DTXSID301016924
Chemical and physical data
Formula	C16H23NO
Molar mass	245.366 g·mol−1
3D model (JSmol)	Interactive image
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

The President of the Republic of Italy classified cathinone and all structurally derived analogues (including pyrovalerone analogues) as narcotics in January 2012.^[11][12]

Sweden's public health agency suggested to classify α-PHP as narcotic on June 1, 2015.^[13]

As of October 2015, α-PHP is a controlled substance in China.^[14]

In December 2019, the UNODC announced scheduling recommendations placing Alpha-PHP into Schedule II.^[15]

As of 29 October 2021, α-PHP has been banned in the Netherlands under the 1971 Vienna Convention on Psychotropic Substances.^[16]

In the US, a-PHP is a Schedule I controlled substance as of 2022.^[17]

See also

• α-PHiP
• α-PHPP
• α-PBP
• α-PPP
• A-PCyP
• 4F-PHP
• 4-Cl-PHP
• 4-Methyl-α-PHP
• Prolintane
• Pyrovalerone
• MDPV
• MDPHP

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 - α-Pyrrolidino ketones". Ernst Seeger. Archived from the original on 19 June 2015. Retrieved 18 June 2015.
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. "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.
12. "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.
13. "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Archived from the original on 1 July 2015. Retrieved 29 June 2015.
14. "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.
15. "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling". Archived from the original on 2020-09-26. Retrieved 2021-05-31.
16. "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.
17. 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". Federal Register. Drug Enforcement Administration. Retrieved 2024-04-23.