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
oral, intranasal, vaporization, intravenous, rectal, sublingual
Identifiers
14530-33-7 YesY 5485-65-4 (HCl)
PubChem CID 11148955
ChemSpider 9324063 YesY
ChEMBL CHEMBL205082 YesY
Chemical data
Formula C15H21NO
231.333 g/mol
 YesY (what is this?)  (verify)

α-Pyrrolidinopentiophenone (alpha-pyrrolidinovalerophenone, α-PVP, alpha-PVP, O-2387, β-ketone-prolintane, Prolintanone) is a synthetic stimulant drug of the cathinone class developed in the 1960s sometimes called flakka. It 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]

Mechanism of action[edit]

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),[4] although no substantial research on this compound has been conducted.

Toxicology[edit]

α-PVP has been reported to be the cause or a significant contributory cause of death in suicides and polydrug overdoses.[5][6] α-PVP can cause a condition called "excited delirium" that involves hyperstimulation, paranoia, and hallucinations.[7] α-PVP has also been linked to at least one death where it was combined with pentedrone and caused heart failure.[8]

Detection in biological specimens[edit]

α-PVP may be quantitated 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.[9][10]

Legal status[edit]

α-PVP is a Schedule I drug in New Mexico, Delaware, 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.[11] 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.[12]

Some users become paranoid while on the drug.[13]

Marketing[edit]

α-PVP is sometimes the active ingredient in recreational drugs sold as "bath salts".[12] 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 "hit", and a laboratory for one county in Florida has reported a steady rise in α-PVP detections, from none in seized drugs in January–February 2014 to 84 in September 2014.[14]

See also[edit]

References[edit]

  1. ^ Sauer, Christoph; Peters, Frank T.; Haas, Claudia; Meyer, Markus R.; Fritschi, Giselher; Maurer, Hans H. (2009). "New designer drug α-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. doi:10.1002/jms.1571. PMID 19241365. 
  2. ^ "SOFT Designer Drug Committee Monographs: Alpha-PVP" (PDF). Society of Forensic Toxicologists. September 13, 2013. 
  3. ^ "U.S. Criminalizes Designer Drugs". American Chemical Society. August 27, 2012. 
  4. ^ Meltzer, P. C.; Butler, D; Deschamps, J. R.; Madras, B. K. (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): 1420–32. doi:10.1021/jm050797a. PMC 2602954. PMID 16480278. 
  5. ^ Marinetti, L. J.; Antonides, H. M. (2013). "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. doi:10.1093/jat/bks136. PMID 23361867. 
  6. ^ Waugh et al. (2013). "Deaths Involving the Recreational Use of α-PVP (α-pyrrolidinopentiophenone)" (PDF). AAFS Proceedings. Abstract K16. 
  7. ^ Template:Cite url = http://www.drugabuse.gov/drugs-abuse/emerging-trends
  8. ^ Sykutera, M.; Cychowska, M.; Bloch-Boguslawska, E. (2015). "A Fatal Case of Pentedrone and -Pyrrolidinovalerophenone Poisoning". Journal of Analytical Toxicology. doi:10.1093/jat/bkv011. 
  9. ^ Eiden, C.; Mathieu, O.; Catala, P. (2013). "Toxicity and death following recreational use of 2-pyrrolidino valerophenone.". Clinical Toxicology. doi:10.3109/15563650.2013.847187. 
  10. ^ Baselt RC (2014). Disposition of toxic drugs and chemicals in man. Seal Beach, Ca.: Biomedical Publications. p. 1751. ISBN 978-0-9626523-9-4. 
  11. ^ "2014 Rules, DEA/DOJ Diversion Control". 
  12. ^ a b Olding, Rachel. "'Bath salts' death: lethal drug was a top seller". The Sydney Morning Herald. 
  13. ^ "Naked paranoids begging police to save them? That's flakka!". Reuters. 30 Apr 2015. 
  14. ^ Tonya Alvarez (April 2, 2015). "Flakka: Rampant designer drug dubbed '$5 insanity'". Sun-Sentinel (Fort Lauderdale, Fla.).