Alpha-Pyrrolidinopentiophenone Explained

α-Pyrrolidinopentiophenone (also known as α-pyrrolidinovalerophenone, α-PVP, O-2387, β-keto-prolintane, prolintanone,[1] [2] 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.[3] [4] α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.[5]

Colloquially, it is sometimes called flakka, gravel, or the zombie drug.[6] [7]

Adverse effects

α-PVP, like other psychostimulants, can cause hyperstimulation, paranoia, and hallucinations.[8] 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.[9] [10] [11] [12] 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.[13]

According to Craig Crespi in the journal Case Reports in Psychiatry, "symptoms are known to easily escalate into frightening delusions, paranoid psychosis, extreme agitation, and a multitude of other 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.[14]

Pharmacology

α-PVP acts as a norepinephrine-dopamine reuptake inhibitor similar to methylphenidate and cocaine with IC50 values of 14.2 and 12.8 nM, respectively, similar to its methylenedioxy derivative MDPV.[15] [16] [17] [18] Similar to other cathinones, α-PVP has been shown to have reinforcing effects in rats.[19] [20]

Chemistry

α-PVP gives no reaction with the Marquis reagent. It gives a grey/black reaction with the Mecke reagent.[21]

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.[22] [23]

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,[15] as well as the Czech Republic.[24]

Australia

α-PVP is a Schedule 9 prohibited substance under the Poisons Standard (July 2016).[25] 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. 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.[26] [27]

EU

α-PVP was required to be banned by EU member states by 3 July 2017[28] 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.[29]

Italy

Cathinone and all structurally derived analogues (including pyrovalerone analogues) were classified as narcotics in January 2012.[30] [15]

US

On 28 January 2014, the DEA listed α-PVP, along with nine other synthetic cathinones, on the Schedule 1 with a temporary ban, effective February 27, 2014.[31] The temporary ban was then extended.[32]

Notes and References

  1. Web site: May 9, 2023 . PubChem Substance Record for SID 481087126, alpha-PVP . May 7, 2024 . National Center for Biotechnology Information.
  2. Web site: March 3, 2023 . PubChem Substance Record for SID 172113243, alpha-Pyrrolidinovalerophenone . May 7, 2024 . National Center for Biotechnology Information.
  3. α-Pyrrolidinovalerophenones . May 29, 1963 . GB . 927475.
  4. Web site: Logan BK . SOFT Designer Drug Committee Monographs: Alpha-PVP . September 13, 2013 . Society of Forensic Toxicologists . https://web.archive.org/web/20150406202220/http://www.soft-tox.org/files/Designer_Drugs/Alpha-PVP.pdf . April 6, 2015 .
  5. Sauer C, Peters FT, Haas C, Meyer MR, Fritschi G, Maurer HH . June 2009 . New designer drug alpha-pyrrolidinovalerophenone (PVP): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques . Journal of Mass Spectrometry . 44 . 6 . 952–64 . 2009JMSp...44..952S . 10.1002/jms.1571 . 19241365.
  6. Web site: 'Zombie drug' flakka may have hit Winnipeg streets: police. CBC News. November 2, 2017. Coubrough J .
  7. Web site: Flakka: What is the 'zombie drug' blamed for face-eating attacks?. https://web.archive.org/web/20160818194424/http://www.independent.co.uk/news/world/americas/flakka-what-is-it-florida-face-eating-attack-zombie-drug-austin-harrouff-a7195871.html . 2016-08-18 . limited . live. The Independent. August 17, 2016. England C, Garcia F .
  8. Web site: Drugs of Abuse Emerging Trends. National Institute on Drug Abuse. 6 April 2015.
  9. Marinetti LJ, Antonides HM . Analysis of synthetic cathinones commonly found in bath salts in human performance and postmortem toxicology: method development, drug distribution and interpretation of results . Journal of Analytical Toxicology . 37 . 3 . 135–46 . April 2013 . 23361867 . 10.1093/jat/bks136 . free .
  10. Richards-Waugh LL, Bailey KM, Clay DJ, Gebhardt MA, Newsome-Sparks CL, Majmoud HE, Venuti SE, Kraner JC . 2013 . AAFS Proceedings . Abstract K16 . t . 2015-04-03 . https://web.archive.org/web/20161108233911/http://www.aafs.org/sites/default/files/pdf/ProceedingsWashingtonDC2013.pdf . 2016-11-08 .
  11. News: 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 .
  12. Klavž J, Gorenjak M, Marinšek M . 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 . 121–4 . August 2016 . 26890319 . 10.1016/j.forsciint.2016.01.018 .
  13. Sykutera M, Cychowska M, Bloch-Boguslawska E . A Fatal Case of Pentedrone and α-Pyrrolidinovalerophenone Poisoning . Journal of Analytical Toxicology . 39 . 4 . 324–9 . May 2015 . 25737339 . 10.1093/jat/bkv011 .
  14. Mash DC . Excited Delirium and Sudden Death: A Syndromal Disorder at the Extreme End of the Neuropsychiatric Continuum . Frontiers in Physiology . 7 . 435 . 2016 . 27790150 . 5061757 . 10.3389/fphys.2016.00435 . free .
  15. Web site: 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.
  16. Marusich JA, Antonazzo KR, Wiley JL, Blough BE, Partilla JS, Baumann MH . Pharmacology of novel synthetic stimulants structurally related to the "bath salts" constituent 3,4-methylenedioxypyrovalerone (MDPV) . Neuropharmacology . 87 . 206–13 . December 2014 . 24594476 . 4152390 . 10.1016/j.neuropharm.2014.02.016 .
  17. Rickli A, Hoener MC, Liechti ME . Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones . European Neuropsychopharmacology . 25 . 3 . 365–76 . March 2015 . 25624004 . 10.1016/j.euroneuro.2014.12.012 . 5511568 .
  18. Meltzer PC, Butler D, Deschamps JR, Madras BK . 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 . 1420–32 . February 2006 . 16480278 . 2602954 . 10.1021/jm050797a .
  19. Gannon BM, Galindo KI, Mesmin MP, Sulima A, Rice KC, Collins GT . Relative reinforcing effects of second-generation synthetic cathinones: Acquisition of self-administration and fixed ratio dose-response curves in rats . Neuropharmacology . 134 . Pt A . 28–35 . May 2018 . 28811192 . 5809320 . 10.1016/j.neuropharm.2017.08.018 .
  20. Gannon BM, Rice KC, Collins GT . Reinforcing effects of abused 'bath salts' constituents 3,4-methylenedioxypyrovalerone and α-pyrrolidinopentiophenone and their enantiomers . Behavioural Pharmacology . 28 . 7 . 578–581 . October 2017 . 28570297 . 5599337 . 10.1097/FBP.0000000000000315 .
  21. Web site: Reactions table . Reagent Base . 3 December 2015 . https://web.archive.org/web/20151208180616/http://reagent-base.net/reagents-table/ . 2015-12-08 .
  22. Eiden C, Mathieu O, Cathala P, Debruyne D, Baccino E, Petit P, Peyriere H . Toxicity and death following recreational use of 2-pyrrolidino valerophenone . Clinical Toxicology . 51 . 9 . 899–903 . November 2013 . 24111554 . 10.3109/15563650.2013.847187 . 22826544 .
  23. Book: Baselt RC . Disposition of toxic drugs and chemicals in man . 2014 . Biomedical Publications . Seal Beach, Ca. . 978-0-9626523-9-4 . 1751 .
  24. Web site: Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) . Ministerstvo zdravotnictví . https://web.archive.org/web/20200515081621/https://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf . 2020-05-15 . cs.
  25. Poisons Standard July 2016 Comlaw.gov.au
  26. News: Olding R . 'Bath salts' death: lethal drug was a top seller . The Sydney Morning Herald.
  27. Web site: Flakka, synthetic drug behind increasingly bizarre crimes. AP. 30 Apr 2015. 30 April 2015. 2 May 2015. https://web.archive.org/web/20150502232931/http://bigstory.ap.org/article/f3667988d0e042cfbb9b40838a78ab65/naked-paranoids-begging-police-save-them-thats-flakka. dead.
  28. Web site: Council Implementing Decision (EU) 2016/1070 of 27 June 2016 on subjecting α-PVP to control measures . 2021-08-13 . eur-lex.europa.eu.
  29. Web site: http://www.sfda.gov.cn/WS01/CL0056/130753.html . zh: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 . 27 September 2015 . zh . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 .
  30. Web site: Decreto 29 dicembre 2011 (12A00013) (G.U. Serie Generale n. 3 del 4 gennaio 2012) . 2016-05-28 . https://web.archive.org/web/20160701171219/http://www.politicheantidroga.it/media/491607/decreto%20ministero%20salute%2029%20dicembre%202011.pdf . 2016-07-01 .
  31. Web site: Rules - 2014 . DEA/DOJ Diversion Control . 2014-02-01 . 2016-10-17 . https://web.archive.org/web/20161017130614/https://www.deadiversion.usdoj.gov/fed_regs/rules/2014/fr0128.htm . dead .
  32. News: Flakka: The New Illegal Drug You Need to Know About . Inc. . November 8, 2015 . November 11, 2015 . Steinberg J .
  33. News: Flakka: Rampant designer drug dubbed '$5 insanity' . . Fort Lauderdale, Fla. . Alvarez T . April 2, 2015.
  34. Web site: Lists of:Scheduling Actions, Controlled Substances, Regulated Chemicals|author= |date=August 2016|website=US Department of Justice |access-date= September 29, 2016}}

    Economics

    α-PVP is sometimes the active ingredient in recreational drugs sold as "bath salts

    ]". 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

    References

    .

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