alpha-Pyrrolidinopentiophenone

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This article is about the drug substance α-PVP. For the pharmaceutical excipient called PVP, see polyvinylpyrrolidone.
alpha-Pyrrolidinopentiophenone
Ball-and-stick model of the alpha-PVP molecule
Clinical data
Routes of
administration		By mouth, intranasal, vaporization, intravenous, sublingual
Legal status
Legal status
Identifiers
  • (RS)-1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-one
JSmol)
  • CCCC(C(C1=CC=CC=C1)=O)N2CCCC2
  • InChI=1S/C15H21NO/c1-2-8-14(16-11-6-7-12-16)15(17)13-9-4-3-5-10-13/h3-5,9-10,14H,2,6-8,11-12H2,1H3 checkY
  • Key:YDIIDRWHPFMLGR-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

α-Pyrrolidinopentiophenone (also known as α-pyrrolidinovalerophenone, α-PVP, O-2387, β-keto-prolintane, prolintanone,[citation needed] or desmethylpyrovalerone) is a synthetic stimulant of the cathinone class developed in the 1960s that has been sold as a designer drug and often consumed for recreational reasons.[2][3] α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.[4]

Colloquially, it is sometimes called flakka, gravel and the zombie drug.[5][6]

Adverse effects

α-PVP, like other psychostimulants, can cause hyperstimulation, paranoia, and hallucinations.[7] α-PVP has been reported to be the cause, or a significant contributory cause of death in suicides and overdoses caused by combinations of drugs.[8][9][10][11] α-PVP has also been linked to at least one death with pulmonary edema and moderately advanced atherosclerotic coronary disease when it was combined with pentedrone.[12]

According to Craig Crespi in the journal

altered mental states
." These common adverse effects of α-PVP are in line with other psychostimulants.

In addition, agitated delirium has been named as an adverse effect of α-PVP.[13]

Pharmacology

α-PVP acts as a

cathinones, α-PVP has been shown to have reinforcing effects in rats.[18][19]

Chemistry

α-PVP gives no reaction with the Marquis reagent. It gives a grey/black reaction with the Mecke reagent.[20]

Detection in body fluids

α-PVP may be quantified in blood, plasma or urine by

liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma α-PVP concentrations are expected to be in a range of 10–50 μg/L in persons using the drug recreationally, >100 μg/L in intoxicated patients and >300 μg/L in victims of acute overdosage.[21][22]

Society and culture

Legal status

α-PVP is banned in Estonia, Finland, France, Germany, Hungary, Russia, Ireland, Latvia, Lithuania, Netherlands, Poland, Romania, Slovenia, Sweden, United Kingdom, Turkey, Norway,[14] as well as the Czech Republic.[23]

Australia

α-PVP is a Schedule 9 prohibited substance under the Poisons Standard (July 2016).[24] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[24] The drug was explicitly made illegal in New South Wales after it was illegally marketed with the imprimatur of erroneous legal advice that it was not encompassed by analog provisions of the relevant act. It is encompassed by those provisions, and therefore has been illegal for many years in New South Wales. The legislative action followed the death of two individuals from using it; one jumping off a balcony, another having a heart attack after a state of delirium.[25][26]

EU

α-PVP was required to be banned by EU member states by 3 July 2017[27] and appears in Schedule II of the UN Convention on Psychotropic Substances.

China

As of October 2015, α-PVP is a controlled substance in China.[28]

Italy

Cathinone and all structurally derived analogues (including pyrovalerone analogues) were classified as narcotics in January 2012.[29][14]

US

On 28 January 2014, the

Schedule 1 with a temporary ban, effective February 27, 2014.[30] The temporary ban was then extended.[31]

Economics

α-PVP is sometimes the active ingredient in recreational drugs sold as "bath salts".[25] It may also be distinguished from "bath salts" and sold under a different name: "flakka", a name used in Florida, or "gravel" in other parts of the U.S. It is reportedly available as cheaply as US$5 per dose.[32] A laboratory for one county in Florida reported a steady rise in α-PVP detections in seized drugs from none in January–February 2014 to 84 in September 2014.[33]

See also

Notes

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. ^ GB 927475, "α-Pyrrolidinovalerophenones", published May 29, 1963 
  3. ^ Logan BK (September 13, 2013). "SOFT Designer Drug Committee Monographs: Alpha-PVP" (PDF). Society of Forensic Toxicologists. Archived from the original (PDF) on April 6, 2015.
  4. PMID 19241365
    .
  5. ^ Coubrough J (November 2, 2017). "'Zombie drug' flakka may have hit Winnipeg streets: police". CBC News.
  6. ^ England C, Garcia F (August 17, 2016). "Flakka: What is the 'zombie drug' blamed for face-eating attacks?". The Independent. Archived from the original on 2016-08-18.
  7. ^ "Drugs of Abuse Emerging Trends". National Institute on Drug Abuse. 6 April 2015.
  8. PMID 23361867
    .
  9. ^ Richards-Waugh LL, Bailey KM, Clay DJ, Gebhardt MA, Newsome-Sparks CL, Majmoud HE, Venuti SE, Kraner JC (2013). "t" (PDF). AAFS Proceedings. Abstract K16. Archived from the original (PDF) on 2016-11-08. Retrieved 2015-04-03.
  10. ^ "Cheap, synthetic 'flakka' dethroning cocaine on Florida drug scene". 27 people have died from flakka-related overdoses in the last eight months in Broward County
  11. PMID 26890319
    .
  12. PMID 25737339
    .
  13. PMID 27790150
    .
  14. ^ a b c "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.
  15. PMID 24594476
    .
  16. S2CID 5511568
    .
  17. PMID 16480278
    .
  18. PMID 28811192
    .
  19. PMID 28570297
    .
  20. ^ "Reactions table". Reagent Base. Archived from the original on 2015-12-08. Retrieved 3 December 2015.
  21. S2CID 22826544
    .
  22. ISBN 978-0-9626523-9-4
    .
  23. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2020-05-15.
  24. ^ a b Poisons Standard July 2016 Comlaw.gov.au
  25. ^ a b Olding R. "'Bath salts' death: lethal drug was a top seller". The Sydney Morning Herald.
  26. ^ "Flakka, synthetic drug behind increasingly bizarre crimes". AP. 30 Apr 2015. Archived from the original on 2 May 2015. Retrieved 30 April 2015.
  27. ^ "Council Implementing Decision (EU) 2016/1070 of 27 June 2016 on subjecting α-PVP to control measures". eur-lex.europa.eu. Retrieved 2021-08-13.
  28. ^ 关于印发《非药用类麻醉药品和精神药品列管办法》的通知. China Food and Drug Administration (in Chinese). 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  29. ^ "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. Retrieved 2016-05-28.
  30. ^ "Rules - 2014". DEA/DOJ Diversion Control. Archived from the original on 2016-10-17. Retrieved 2014-02-01.
  31. ^ "Lists of:Scheduling Actions, Controlled Substances, Regulated Chemicals" (PDF). US Department of Justice. August 2016. Retrieved September 29, 2016.
  32. ^ Steinberg J (November 8, 2015). "Flakka: The New Illegal Drug You Need to Know About". Inc. Retrieved November 11, 2015.
  33. Sun-Sentinel
    . Fort Lauderdale, Fla.
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