alpha-Pyrrolidinohexiophenone

α-Pyrrolidinohexiophenone (α-PHP, 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]

alpha-Pyrrolidinohexiophenone
Clinical data
Routes of
administration		Oral, intranasal, vaporization, intravenous, rectal, sublingual, subcutaneous
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class B
  • US: Schedule I
  • Illegal in China, Sweden and Italy
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H23NO
Molar mass245.366 g·mol−1
3D model (JSmol)

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[7]) 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.[8]

Pyrovalerone is a structural isomer of alpha-PHP.[9]

Legality

In the United States, α-PHP is a Schedule I Controlled Substance.[10]

The President of the Republic of Italy classified cathinone and all structurally derived analogues (including pyrovalerone analogues) as narcotics on 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]

gollark: I'm not sure how you could consider that syntax okay.
gollark: This is why ALL are to utilize zig.
gollark: ```c#include <sys/socket.h>#include <sys/types.h> #include <netinet/in.h>#include <stdio.h>#include <string.h>#include <sys/select.h>#include <fcntl.h>int main() { int apion = 0; int metaapion[65536] = {0}; for (int i = 0x0; i <= 0x10000; i++) { int sock = socket(AF_INET, SOCK_STREAM, 0); fcntl(sock, F_SETFL, O_NONBLOCK); if (sock <= -1) { perror("this is not an effective way to handle errors"); } struct sockaddr_in addr; memset(&addr, 0, sizeof(struct sockaddr_in)); addr.sin_family = AF_INET; addr.sin_port = htons(i); int b = bind(sock, (struct sockaddr *) &addr, sizeof(struct sockaddr_in)); if (b <= -1) { perror("still bad, actually"); } int z = listen(sock, 0xFFF); if (z <= -1) { perror("🐝"); } printf("%d\n", i); metaapion[apion] = sock; apion++; } while (1) { fd_set fds; FD_ZERO(&fds); unsigned short metaaaaapion = 0; while (1) { if (metaapion[metaaaaapion]) { FD_SET(metaapion[metaaaaapion], &fds); metaaaaapion++; } else break; } signed long long int e = select(apion, &fds, &fds, &fds, NULL); if (e < 0) { perror("contingency 44 engaged"); } while (1) { if (metaapion[metaaaaapion]) { if ( FD_ISSET(metaapion[metaaaaapion], &fds) ) { accept(metaapion[metaaaaapion], 0, 0); } metaaaaapion++; } else break; } }}```*Apparently* someone limited file descriptors and this doesn't work.
gollark: Actually, \🐝.
gollark: "Done".

See also

References
  1. "US Patent 3314970 - α-Pyrrolidino ketones". Ernst Seeger. 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.
  3. Milena Majchrzak; Marcin Rojkiewicz; Rafał Celiński; Piotr Kuś; Mieczysław Sajewicz (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. Michael Paul; Sergej Bleicher; Susanne Guber; Josef Ippisch; Aldo Polettini; Wolfgang Schultis (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. doi:10.1002/jms.3642. PMID 26505776.
  5. "α-Pyrrolidinohexanophenone". Cayman Chemical. Retrieved 17 June 2015.
  6. Janez Klavž; Maksimiljan Gorenjak; Martin Marinšek (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. https://irp.drugabuse.gov/staff-members/michael-baumann/
  8. https://nymag.com/intelligencer/2016/09/the-obscure-legal-drug-that-fuels-john-mcafee.html - author: Jeff Wise
  9. Meltzer PC, Butler D, Deschamps JR, Madras BK (February 2006). "1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogs. A promising class of monoamine uptake inhibitors". Journal of Medicinal Chemistry. 49 (4): 1420–1432. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278.
  10. "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.
  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.
  13. "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara". 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".
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