alpha-Pyrrolidinopentiophenone

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alpha-Pyrrolidinopentiophenone
Alpha-Pyrrolidinopentiophenone.svg
Ball-and-stick model of the alpha-PVP molecule
Systematic (IUPAC) name
(RS)-1-Phenyl-2-(1-pyrrolidinyl)-1-pentanone
Clinical data
Legal status
Routes of
administration
oral, intranasal, vaporization, intravenous, rectal, sublingual
Identifiers
CAS Number 14530-33-7 YesY 5485-65-4 (HCl)
PubChem CID: 11148955
ChemSpider 9324063 YesY
ChEMBL CHEMBL205082 YesY
Chemical data
Formula C15H21NO
Molecular mass 231.333 g/mol
  (verify)

α-Pyrrolidinopentiophenone (also known as alpha-pyrrolidinovalerophenone, α-PVP, alpha-PVP, O-2387, β-keto-prolintane, Prolintanone, or Desmethyl Pyrovalerone) is a synthetic stimulant drug of the cathinone class developed in the 1960s. Colloquially it is sometimes called flakka or gravel. α-PVP is chemically related to pyrovalerone and is the ketone analog of prolintane.[1] It is used as a recreational drug,[2] and is considered a Schedule I drug under the Food and Drug Administration Safety and Innovation Act.[3]

Adverse effects

α-PVP can cause a condition called "excited delirium" that involves hyperstimulation, paranoia, and hallucinations.[4] 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.[5][6][7] α-PVP has also been linked to at least one death where it was combined with pentedrone and caused heart failure.[8]

Pharmacology

The mechanism of action is unknown for α-PVP. It is believed to act similarly to the designer drug MDPV, which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI),[9] although no substantial research on this compound has been conducted.

Physical and chemical properties

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.[10][11]

Chemistry

a-PVP gives no reaction with the marquis reagent. It gives a grey/black reaction with the mecke reagent.[12]

Society and culture

Legal status

α-PVP is a Schedule I drug in New Mexico, Delaware, Florida, Oklahoma, and Virginia. On January 28, 2014, the U.S. DEA listed it, along with nine other synthetic cathinones, on the Schedule 1 with a temporary ban, effective February 27, 2014.[13] 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.[14][15]

As of October 2015 α-PVP is a controlled substance in China.[16]

Economics

α-PVP is sometimes the active ingredient in recreational drugs sold as "bath salts".[14] 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 typically manufactured in China, India, or Pakistan and repackaged in gram packets in the U.S., and it is possible to mix it with higher-priced drugs such as heroin, cocaine, or methamphetamine. It is reportedly available as cheaply as US$5 per dose.[17] 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.[18]

See also

References

  1. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  2. "SOFT Designer Drug Committee Monographs: Alpha-PVP" (PDF). Society of Forensic Toxicologists. September 13, 2013.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  3. "U.S. Criminalizes Designer Drugs". American Chemical Society. August 27, 2012.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. "Drugs of Abuse Emerging Trends". National Institute on Drug Abuse. 6 April 2015.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  5. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  6. Waugh; et al. (2013). "Deaths Involving the Recreational Use of α-PVP (α-pyrrolidinopentiophenone)" (PDF). AAFS Proceedings. Abstract K16.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  7. "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<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  8. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  9. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  10. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  11. Baselt RC (2014). Disposition of toxic drugs and chemicals in man. Seal Beach, Ca.: Biomedical Publications. p. 1751. ISBN 978-0-9626523-9-4.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  12. "Reactions table". Reagent Base. Retrieved 3 December 2015.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  13. "2014 Rules, DEA/DOJ Diversion Control".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  14. 14.0 14.1 Olding, Rachel. "'Bath salts' death: lethal drug was a top seller". The Sydney Morning Herald.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  15. "Flakka, synthetic drug behind increasingly bizarre crimes". AP. 30 Apr 2015.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  16. "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. Retrieved 1 October 2015. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  17. Joseph Steinberg (November 8, 2015). "Flakka: The New Illegal Drug You Need to Know About". Inc. Retrieved November 11, 2015.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  18. Tonya Alvarez (April 2, 2015). "Flakka: Rampant designer drug dubbed '$5 insanity'". Sun-Sentinel. Fort Lauderdale, Fla.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>