Methylenedioxypyrovalerone

Source: Wikipedia, the free encyclopedia.
(Redirected from
MDPV
)

Methylenedioxypyrovalerone
rectal, vaporization
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F1 (Prohibited narcotics)
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II[1]
  • Illegal in Austria, Belgium, Bulgaria, Croatia, Cyprus, Czech Republic, Denmark, Estonia, France, Hungary, Ireland, Finland, Italy, Latvia, Luxembourg, Norway, Poland, Portugal, Romania, Russia, Slovakia, Slovenia, Sweden, Turkey,[2] Ukraine.
renal
)
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
JSmol)
ChiralityRacemic mixture
  • O=C(C(CCC)N1CCCC1)C2=CC=C3C(OCO3)=C2
  • InChI=1S/C16H21NO3/c1-2-5-13(17-8-3-4-9-17)16(18)12-6-7-14-15(10-12)20-11-19-14/h6-7,10,13H,2-5,8-9,11H2,1H3 checkY
  • Key:SYHGEUNFJIGTRX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Methylenedioxypyrovalerone (MDPV) is a

K2 as incense, until it was banned in 2011.[6]

Appearance

The hydrochloride salt exists as a very fine crystalline powder; it is

hygroscopic and thus tends to form clumps, resembling something like powdered sugar. Its color can range from pure white to a yellowish-tan and has a slight odor that strengthens as it colors. Impurities are likely to consist of either pyrrolidine or alpha-dibrominated alkylphenones—respectively, from either excess pyrrolidine or incomplete amination during synthesis. These impurities likely account for its discoloration and fishy (pyrrolidine) or bromine-like odor, which worsens upon exposure to air, moisture, or bases.[7]

Pharmacology

Methylenedioxypyrovalerone has no record of FDA approved

medical use.[8] It has been shown to produce robust reinforcing effects and compulsive self-administration in rats, though this had already been provisionally established by a number of documented cases of misuse and addiction in humans before the animal tests were carried out.[9][10]

MDPV is the 3,4-methylenedioxy ring-substituted analog of the compound pyrovalerone, developed in the 1960s, which has been used for the treatment of chronic fatigue and as an anorectic, but caused problems of abuse and dependence.[11]

Other drugs with a similar chemical structure include

(α-PVP).

Effects

MDPV acts as a stimulant and has been reported to produce effects similar to those of cocaine, methylphenidate, and amphetamines.[12]

The primary psychological effects have a duration of roughly 3 to 4 hours, with aftereffects such as

cravings to re-administer.[12][13]

Reported modalities of intake include oral consumption,

intravenous use. It is supposedly active at 3–5 mg, with typical doses ranging between 5–20 mg.[12]

When assayed in mice, repeated exposure to MDPV causes not only an anxiogenic effect but also increased aggressive behaviour, a feature that has already been observed in humans. As with MDMA, MDPV also caused a faster adaptation to repeated social isolation.[14]

A cross-sensitization between MDPV and cocaine has been evidenced.[15] Furthermore, both psychostimulants, MDPV and cocaine, restore drug-seeking behavior with respect to each other, although relapse into drug-taking is always more pronounced with the conditioning drug. Moreover, memories associated with MDPV require more time to be extinguished. Also, in MDPV-treated mice, a priming-dose of cocaine triggers significant neuroplasticity, implying a high vulnerability to its abuse.[16]

Long-term effects

The long-term effects of MDPV on humans have not been studied, but it has been reported that mice treated with MDPV during adolescence show reinforcing behavior patterns to cocaine that are higher than the control groups. These behavioural changes are related to alterations of factor expression directly related to addiction. All this suggests an increased vulnerability to cocaine abuse.[17]

Metabolism

MDPV undergoes

COMT phase 1 metabolism (liver) into methylcatechol and pyrrolidine, which in turn are glucuronated (uridine 5'-diphospho-glucuronosyl-transferase) allowing it to be excreted by the kidneys, with only a small fraction of the metabolites being excreted into the stools.[19] No free pyrrolidine will be detected in the urine.[20]

Molecularly, this is seen as demethylenation of methylenedioxypyrovalerone (

catechol-O-methyl transferase. Hydroxylation of both the aromatic ring and side chain then takes place, followed by an oxidation of the pyrrolidine ring to the corresponding lactam, with subsequent detachment and ring opening to the corresponding carboxylic acid.[21]

Detection in biological specimens

MDPV may be quantified in blood, plasma or urine by gas chromatography-mass spectrometry or 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 MDPV concentrations are expected to be in a range of 10–50 μg/L in persons using the drug recreationally, >50 μg/L in intoxicated patients, and >300 μg/L in victims of acute overdose.[22]

Legality

In the UK, following the ACMD's report on substituted cathinone derivatives,[13] MDPV is a Class B drug under The Misuse of Drugs Act 1971 (Amendment) Order 2010, making it illegal to sell, buy, or possess without a license.[23][24]

MDPV is specifically listed as a controlled substance in Finland (listed appendix IV substance as of June 28, 2010),[25] Denmark and Sweden. In Sweden a 33-year-old man has been sentenced to six years in prison by an appellate court, Hovrätt, for possession of 250 grams of MDPV that had been acquired prior to criminalization.[26]

Australia

In Western Australia, MDPV has been banned under the Poisons Act 1964, having been included in Appendix A Schedule 9 of the Poisons Act 1964 as from February 11, 2012. The Director of Public Prosecutions for Western Australia announced that anyone intending to sell or supply MDPV faces a maximum $100,000 fine or 25 years in jail. Users face a $2000 fine or two years' jail. Therefore, anyone caught with MDPV can be charged with possession, selling, supplying or intent to sell or supply.[27]

Canada

Canadian Health Minister Leona Aglukkaq announced on June 5, 2012, that MDPV would be listed on Schedule I of the Controlled Drugs and Substances Act, which was realized on September 26, 2012.[28]

United States

In the United States, MDPV is a DEA federally scheduled drug. On October 21, 2011, the DEA issued a temporary one-year ban on MDPV, classifying it as a schedule I substance. Schedule I status is reserved for substances with a high potential for abuse, no currently accepted use for treatment in the United States and a lack of accepted safety standards for use under medical supervision.[29]

Before the federal ban was announced, MDPV was already banned in Louisiana and Florida.[30] On March 24, 2011, Kentucky passed bill HB 121, which makes MDPV, as well as three other cathinones, controlled substances in the state. It also makes it a Class A misdemeanor to sell the drug, and a Class B misdemeanor to possess it.[31]

MDPV is banned in New Jersey under Pamela's Law. The law is named after Pamela Schmidt, a Rutgers University student who was murdered in March 2011 by an alleged user of MDPV.[32] A toxicology report later found no "bath salts" in his system.[33]

On May 5, 2011, Tennessee Governor Bill Haslam signed a law making it a crime "to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent to produce, manufacture, distribute, sell, or offer for sale" any product containing MDPV.[34]

On July 6, 2011, the governor of Maine signed a bill establishing fines for possession and penalties for trafficking of MDPV.[35]

On October 17, 2011, an Ohio law banning synthetic drugs took effect barring selling and/or possession of "any material, compound, mixture, or preparation that contains any quantity of the following substances having a stimulant effect on the central nervous system, including their salts, isomers, and salts of isomers", listing ephedrine and pyrovalerone. It also specifically includes MDPV.[36] Four days after this Ohio law was passed, the DEA's national emergency ban was implemented.[29]

On December 8, 2011, under the Synthetic Drug Control Act, the

US House of Representatives voted to ban MDPV and a variety of other synthetic drugs that had been legally sold in stores.[37]

Documented fatalities

In April 2011, two weeks after being reported missing, two men in northwestern Pennsylvania were found dead in a remote location on government land. The official cause of death of both men was hypothermia, but toxicology reports later confirmed that both Troy Johnson, 29, and Terry Sumrow, 28, had ingested MDPV shortly before their deaths. "It wasn't anything to kill them, but enough to get them messed up," the county coroner said. MDPV containers were found in their vehicle along with spoons, hypodermic syringes and marijuana paraphernalia. In April 2011, an Alton, Illinois, woman apparently died from an MDPV overdose.[38] In May 2011, the CDC reported a hospital

hemiplegia has been reported.[40]

A total of 107 non-fatal intoxications and 99 analytically confirmed deaths related to MDPV between September 2009 and August 2013 were reported by nine European countries.[2]

Overdose treatment

Physicians often treat MDPV overdose cases with anxiolytics, such as benzodiazepines, to lessen the drug-induced activity in the brain and body.[41] In some cases, general anesthesia was used because sedatives were ineffective.[42]

Treatment in the emergency department for severe hypertension, tachycardia, agitation, or seizures consists of large doses of

beta blockers to treat hypertension in these patients can cause an unopposed peripheral alpha-adrenergic effect with a dangerous paradoxical rise in blood pressure.[43] Electroconvulsive therapy (ECT) has been shown to improve persistent psychotic symptoms associated with repeated MDPV use.[44][45]

See also

References

  1. ^ "Substance Details 3,4-Methylenedioxypyrovalerone". Retrieved January 22, 2024.
  2. ^ a b "EMCDDA–Europol Joint Report on a new psychoactive substance: MDPV (3,4-methylenedioxypyrovalerone)" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). January 2014. Archived (PDF) from the original on August 15, 2016. Retrieved June 27, 2016.
  3. ^
    PMID 23072836
    .
  4. .
  5. ^ US 3478050, Koppe H, Ludwig G, Zeile K, "1-(3',4'-methylenedioxy-phenyl)-2-pyrrolidino-alkanones-(1)", issued November 1969, assigned to CH Boehringer Sohn AG and Co and KG Boehringer Ingelheim GmbH. 
  6. PMID 23288310
    .
  7. .
  8. .
  9. .
  10. .
  11. ^ Seeger E (October 1964). "US Patent 3314970 – α-Pyrrolidino ketones". Boehringer Ingelheim. Archived from the original on June 19, 2015. Retrieved June 27, 2016.
  12. ^ a b c d e f "Report on MDPV" (PDF). Drugs of Concern. DEA. May 2013. Archived (PDF) from the original on June 11, 2016. Retrieved June 27, 2016.
  13. ^ a b "Consideration of the Cathinones" (PDF). Advisory Council on the Misuse of Drugs. March 31, 2010. Archived (PDF) from the original on September 16, 2016. Retrieved June 27, 2016.
  14. S2CID 53208116
    .
  15. .
  16. .
  17. .
  18. .
  19. .
  20. .
  21. .
  22. .
  23. ^ "A change to the Misuse of Drugs Act 1971 : Control of mephedrone and other cathinone derivatives". Home Office. April 16, 2010. Archived from the original on January 25, 2013.
  24. ^ "The Misuse of Drugs Act 1971 (Amendment) Order 2010". Home Office. April 12, 2010. Archived from the original on May 22, 2013. Retrieved November 19, 2012.
  25. ^ Naantalissa A (June 28, 2010). "Finlex: huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen liitteen IV muuttamisesta". Oikeusministeriö (in Finnish). Archived from the original on July 20, 2011. Retrieved January 25, 2011.
  26. ^ "Hovrätten skärper straff i MDPV-dom". Norrköpings Tidningar (in Swedish). June 4, 2010. Archived from the original on March 13, 2016. Retrieved June 27, 2016.
  27. ^ "Emerging drug, MDPV banned in WA". Government of Western Australia. February 8, 2012. Archived from the original on August 15, 2016. Retrieved June 27, 2016.
  28. ^ "'Bath salts' drug ingredient banned in Canada". CBC News. September 26, 2012. Archived from the original on August 11, 2016. Retrieved June 27, 2016.
  29. ^ a b "Chemicals Used in "Bath Salts" Now Under Federal Control and Regulation" (Press release). Drug Enforcement Administration (DEA). October 21, 2011. Archived from the original on August 15, 2016. Retrieved June 27, 2016.
  30. ^ Allen G (February 8, 2011). "Florida Bans Cocaine-Like 'Bath Salts' Sold in Stores". NPR. Archived from the original on February 14, 2019. Retrieved April 2, 2018.
  31. ^ Beshear S (March 23, 2011). "Gov. Beshear signs law banning new synthetic drugs" (Press release). Commonwealth of Kentucky. Archived from the original on May 13, 2016. Retrieved June 27, 2016.
  32. Daily Targum. Archived
    from the original on August 12, 2016. Retrieved June 27, 2016.
  33. ^ Giambusso D (September 2, 2011). "Cranford man charged with murdering girlfriend; Toxicology report shows no trace of 'bath salts'". Nj.com. Archived from the original on March 9, 2014. Retrieved January 27, 2014.
  34. ^ "State of Tennessee Public Chapter No. 169 House Bill No. 457" (PDF). State of Tennessee. April 18, 2011. Archived (PDF) from the original on January 20, 2017. Retrieved June 27, 2016.
  35. ^ "New law sets fine at $350 for 'bath salts' possession". Portland Press Herald. July 7, 2011. Archived from the original on August 16, 2016. Retrieved June 27, 2016.
  36. ^ "Ohio Amendment to Controlled Substances Act HB 64". Ohio General Assembly Archives. October 17, 2011. Archived from the original on June 30, 2015. Retrieved January 11, 2015.
  37. ^ Kreider R (December 8, 2011). "House Votes to Ban 'Spice,' 'Bath Salts'". ABC News. Archived from the original on May 2, 2020. Retrieved June 28, 2020.
  38. ^ Wilson T (May 12, 2011). "Illinois lawmakers target bath salts used as a drug". Chicago Tribune. Archived from the original on August 12, 2016. Retrieved June 27, 2016.
  39. from the original on September 7, 2017. Retrieved September 10, 2017.
  40. .
  41. ^ Salter J, Jim S (April 6, 2011). "Synthetic drugs sent thousands to ER". NBC News. Archived from the original on July 16, 2016. Retrieved June 27, 2016.
  42. ^ Goodnough A, Zezima K (July 16, 2011). "An Alarming New Stimulant, Legal in Many States". New York Times. Archived from the original on April 15, 2021. Retrieved February 27, 2017.
  43. ^ ""Bath Salts" Health Care Provider Fact Sheet" (PDF). Michigan Department of Community Health. April 30, 2012. Archived (PDF) from the original on May 1, 2017. Retrieved June 27, 2016.
  44. S2CID 207428569
    .
  45. .

External links

This page is based on the copyrighted Wikipedia article: MDPV. Articles is available under the CC BY-SA 3.0 license; additional terms may apply.Privacy Policy