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{{Drugbox
{{Drugbox
| verifiedrevid = 446306721
| verifiedrevid = 446306721
⚫
| drug_name = Methylenedioxypyrovalerone
| IUPAC_name = (''RS'')-1-(Benzo[''d''][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
| IUPAC_name = (''RS'')-1-(Benzo[''d''][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
| image = MDPV.svg
| image = MDPV.svg
⚫
| width = 200px
| imagename = 1 : 1 mixture (racemate)
⚫
| image2 = MDPV 3d.gif
⚫
| width = 200px
| width2 = 256px
⚫
| image2 = MDPV 3d.gif
| width2 = 256px
| imagename = 1 : 1 mixture (racemate)
⚫
| drug_name = Methylenedioxypyrovalerone

<!--Clinical data-->
| tradename =
⚫
| legal_status = Unscheduled (illegal in Czech Republic, Denmark and Sweden)
⚫
| routes_of_administration = [[Oral administration|Oral]], [[Insufflation (medicine)|Insufflation]], [[Intravenous]], [[Rectal (medicine)|Rectal]], Vaporization

<!--Pharmacokinetic data-->
⚫
| metabolism = [[Hepatic]]
⚫
| elimination_half-life = <!-- REMOVED; PROBLEMATIC -- 3 to 5 hours {{Citation needed|date=December 2009}} -->
⚫
| excretion = Primarily [[Urine]] ([[Renal]])

<!--Identifiers-->
| CAS_number = 687603-66-3
| CAS_number = 687603-66-3
| CAS_supplemental = <br>{{CAS|24622-62-6}} ([[Hydrochloride|HCl]])
| CAS_supplemental = <br>{{CAS|24622-62-6}} ([[Hydrochloride|HCl]])
⚫
| PubChem = 20111961
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID= 16788110
| ChemSpiderID = 16788110

| ATC_prefix =
<!--Chemical data-->
| ATC_suffix =
⚫
| C=16 | H=21 | N=1 | O=3
⚫
| molecular_weight = 275.343 g/mol (freebase)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SYHGEUNFJIGTRX-UHFFFAOYSA-N
| StdInChIKey = SYHGEUNFJIGTRX-UHFFFAOYSA-N
⚫
| PubChem = 20111961
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
⚫
| C = 16|H = 21|N = 1|O = 3
⚫
| molecular_weight = 275.343 g/mol (freebase)
| melting_point = 209.3
| melting_point = 209.3
| boiling_point = 476
| boiling_point = 476
| bioavailability =
⚫
| metabolism = [[Hepatic]]
⚫
| elimination_half-life = <!-- REMOVED; PROBLEMATIC -- 3 to 5 hours {{Citation needed|date=December 2009}} -->
⚫
| excretion = Primarily [[Urine]] ([[Renal]])
| pregnancy_category =
⚫
| legal_status = Unscheduled (illegal in Czech Republic, Denmark and Sweden)
⚫
| routes_of_administration = [[Oral administration|Oral]], [[Insufflation (medicine)|Insufflation]], [[Intravenous]], [[Rectal (medicine)|Rectal]], Vaporization
}}
}}


Revision as of 21:11, 31 August 2011

Methylenedioxypyrovalerone
Clinical data
Routes of
administration		Oral, Insufflation, Intravenous, Rectal, Vaporization
Legal status
Legal status
  • Unscheduled (illegal in Czech Republic, Denmark and Sweden)
Pharmacokinetic data
MetabolismHepatic
ExcretionPrimarily Urine (Renal)
Identifiers
  • (RS)-1-(Benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H21NO3
Molar mass275.343 g/mol (freebase) g·mol−1
Melting point209.3 °C (408.7 °F)
Boiling point476 °C (889 °F)
  • 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
  (verify)

Methylenedioxypyrovalerone (MDPV) is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI). Reportedly, it has been sold since around 2004 as a designer drug. It is also known as MDPK, MTV, Magic, Maddie, Black Rob, Super Coke and PV.[1] In 2010 it was reportedly sold as a legal drug alternative and marketed in the United States as "bath salts" (under such names as Aura, Blue Silk, Bonzai Grow, Charge Plus, Euphoria, Hurricane Charlie, Ivory Wave, Lovey Dovey, Ocean, Pixie Dust, Red Dove, Scarface, Vanilla Sky, White Dove, White Girl, White Lightning).[2][3]

As a result of adverse effects, incidences of psychological and physical harm have been attributed to MDPV use.[4][5]

Appearance

The hydrochloride salt exists as a very fine, hygroscopic, crystalline powder that tends to clump to itself, 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 pyrollidine or alpha-dibrominated alkylphenones from excess pyrollidine or incomplete amination during production, respectively, and likely accounts for its discoloration and fishy or bromine-like odor which worsens upon exposure to air, moisture, bases, or certain plastics. [6][7]

Pharmacology

MDPV has no history of FDA approved medical use.[8] Reportedly, it has four times the potency of methylphenidate (Ritalin, Concerta).[9] 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.[1] However, despite its structural similarity, the effects of MDPV bear little resemblance to other methylenedioxyphenylalkylamine derivatives such as 3,4-methylenedioxy-N-methylamphetamine (MDMA), instead producing primarily stimulant effects with only mild entactogenic qualities.[1]

Other drugs with a similar chemical structure include α-pyrrolidinopropiophenone (α-PPP), 4'-methyl-α-pyrrolidinopropiophenone (MPPP), 3',4'-methylenedioxy-α-pyrrolidinopropiophenone (MDPPP) and 1-phenyl-2-(1-pyrrolidinyl)-1-pentanone (α-PVP).

Effects

MDPV acts as a stimulant and has been reported to produce effects similar to those of cocaine, methylphenidate, and amphetamines.[1] The acute effects may include:[1][10]

Physiological/Psychological effects

  • tachycardia (Rapid heartbeat)
  • hypertension (High blood pressure)
  • vasoconstriction (Narrowing of the blood vessels)
  • insomnia
  • nausea, stomach cramps, and digestive problems
  • bruxism (Grinding teeth)
  • increased body temperature, chills, sweating
  • pupil dilation
  • headache
  • kidney pain
  • tinnitus
  • dizziness
  • overstimulation
  • breathing difficulty
  • agitation/hypertonia
  • severe paranoia
  • confusion
  • psychotic delusions
  • extreme anxiety/agitation, sometimes progressing to violent behavior
  • suicidal thoughts/actions

Psychiatric symptoms may persist. Physical symptoms may progress to rhabdomyolysis, renal failure, or liver failure.

Desired psychological effects

  • euphoria
  • increased alertness and awareness
  • increased wakefulness and arousal
  • increased energy and motivation
  • mental stimulation/increased concentration
  • increased sociability
  • sexual stimulation/aphrodisiac effects
  • mild empathogenic effects
  • diminished perception of the requirement for food and sleep
  • modification of the symptom profile in early stages of opiate withdrawal consistent with its dopamine reputake inhibitor function; reportedly, attempting to use the drug in management of withdrawal is impossible because of a spectacular (in a neutral or bad sense) and unmanageable complex of side effects, as described in this article, rapidly supervening. The tendency to inhibit norepinephrine reputake would cause a progressive relative worsening of some physical symptoms of opiate withdrawal, generally those that would be subtracted out by clonidine theraphy. [11]

Description of effects

The primary psychological effects have a duration of roughly 3 to 4 hours, with after effects such as tachycardia, hypertension, and mild stimulation lasting from 6 to 8 hours.[1][10] High doses have been observed to cause intense, prolonged panic attacks in stimulant-intolerant users,[1][10] and there are anecdotal reports of psychosis from sleep withdrawal and addiction at higher doses or more frequent dosing intervals.[1][10] MDPV has been distinguished by some for its powers as an aphrodisiac.[1] It has also been repeatedly noted for inducing strong cravings to re-administer.[10][12] Users have reported a compulsive desire to continuously re-dose, even following onset of the unpleasant side effects induced by prolonged use and higher doses.

Extended binges on MDPV have also been reported to produce severe comedown syndrome similar to that of methamphetamine[citation needed], characterized by depression, lethargy, headache, anxiety, postural hypotension (lightheadedness and weakness of the muscles), and in some cases severely bloodshot eyes, which usually subside within 4 to 8 hours. MDPV may also cause temporary bruxism. Side effects are highly dose-dependent. No fatalities have so far been reported without the combination of other substances except for suicide.[1]

Reported modalities of intake include oral consumption, insufflation, smoking, rectal and intravenous use. It is supposedly active at 3–5 mg, with typical doses ranging between 5–20 mg.[1] MDPV loses potency when it is put into solution.[10]

Duration of effects:[13]

Stage Oral Insufflated
Onset 15 - 30 mins 5 - 20 mins
Coming Up 30 - 60 mins 15 - 30 mins
Plateau 30 - 180 mins 30 - 120 mins
Coming Down 30 - 120 mins 30 - 60 mins
After Effects 2 - 48 Hours 2-48 Hours
Total duration: 2.0-7.0 Hours Total duration: 2.0-3.5 Hours

(Note: Duration of effects is highly dose-dependent.)

Metabolism

MDPV undergoes CYP450 2D6, 2C19 and 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 fecal matter.[14] No free pyrrolidine will be detected in the urine.[15]

Molecularly, this is seen as demethylenation of methylenedioxypyrovalerone (CYP2D6), followed by methylation of the aromatic ring via catechol-O-methyl transferase. Then hydroxylation of both the aromatic ring and side chain takes place followed by and oxidation of the pyrimidine ring to the corresponding lactam, with subsequent detachment and ring opening to the corresponding carboxylic acid.[16]

Legality

In the UK, following the ACMD's report on cathinone derivatives,[12] MDPV is a Class B drug under the Misuse of Drugs Act 1971, making it illegal to sell, buy, or possess without a license. Penalties include a maximum of five years and/or unlimited fine for possession; up to 14 years and/or unlimited fine for production or trafficking. See list of drugs illegal in the UK for more information.

In the United States, MDPV is not a scheduled drug (except in Louisiana[1] and Florida[17]), but began appearing on the media radar in early 2011.[18][19][20] 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. [21]On July 6, 2011 the governor of Maine signed a bill establishing fines for possession and penalties for trafficking of MDPV.[22] As of April 15, 2011, two of the chemicals used in making MDPV have been banned in 7 states, including Louisiana, Florida, Alabama, Mississippi, North Dakota, Washington and New Jersey. And, one of the chemicals used in MDPV have been banned in 10 more states, including, Idaho, Utah, Wyoming, New Mexico, Arkansas, Kentucky, Michigan, Virgina, West Virginia and North Carolina.[23] The New Jersey Division of Consumer Affairs made it "a crime to [knowingly] manufacture, distribute, sell, or possess designer drugs labeled as 'bath salts'"[24][25] 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 produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-Methylenedioxypyrovalerone (MDPV).[26]


MDPV is specifically listed as a controlled substance in Finland (listed appendix IV substance as of 28 June 2010),[27] 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.[28]

Documented Misuse

In April, 2011, two weeks after they went missing, two men in Warren County, Pennsylvania were found dead in the Allegheny National Forest. 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," Warren County coroner Jeremiah Borden said. MDPV containers were found in their vehicle along with spoons, hypodermic syringes and marijuana paraphernalia.[29] In April 2011, an Alton, Illinois woman apparently died from an MPDV overdose.[30] In May, 2011, The CDC reported on Emergency Department Visits After Use of "Bath Salts" in Michigan. One person was reported dead on arrival to the ED. Associates of the dead person reported he had used bath salts. His toxicology results revealed high levels of MDPV in addition to marijuana and prescription drugs. The primary factor contributing to death was cited as MDPV toxicity after autopsy was performed.[31]

Treatment

Anyone suspected of having taken MDPV and needing possible treatment should be immediately referred to their personal physician or the nearest poison control center.[32] Physicians often treat MDPV overdose cases with anti-anxiety prescription medications such as Valium and Xanax to lessen the drug-induced activity in the brain and body.[33] In some cases, general anesthesia was used due to sedatives being ineffective [34]

Treatment in the emergency department for severe hypertension, tachycardia, agitation, or seizures consists of large doses of Lorazepam in 2mg to 4mg increments every 10-15 minutes intravenously or intramuscularly. If this is not effective, haloperidol is an option. It has been found that the use of any beta blockers to treat hypertension in these patients can cause an unopposed peripheral alpha-adrenergic effect with a dangerous paradoxical rise in blood pressure. [35]

References

  1. ^ a b c d e f g h i j k l http://194.83.136.209/documents/reports/MDPV.pdf. MDPV report, Psychonaut Research Web Mapping Project
  2. ^ http://www.kmbc.com/news/26256067/detail.html. Abuse Of Fake 'Bath Salts' Sends Dozens To ER in gas stations and convenience stores, similar to the marketing for Spice and K2 as incense.
  3. ^ http://healthybodydaily.com/dr-oz-in-case-you-missed-it/dr-oz-bath-salts-mdpv-bath-salts-drug-over-the-counter. Dr. Oz: Bath Salts| MDPV Bath Salts Drug Over The Counter.
  4. ^ News Desk Manager, Samantha Morgan (9 November 2010). "Parents cautioned against over the counter synthetic speed". NBC 33 News. Retrieved 16 May 2011.
  5. ^ Kelsey Scram (6 January 2011). "Bath Salts Used to Get High". NBC 33 News. Retrieved 16 May 2011.
  6. ^ Brandt, S.; (2010) "Analysis of NRG ‘legal highs’ in the UK: Identification and formation of novel cathinones." doi: 10.1002/dta.204.
  7. ^ Hello and MDPV question - Bluelight
  8. ^ Westphal F, Junge T, Rösner P, Sönnichsen F, Schuster F (2009). "Mass and NMR spectroscopic characterization of 3,4-methylenedioxypyrovalerone: A designer drug with alpha-pyrrolidinophenone structure". Forensic Science International. 190 (1–3): 1. doi:10.1016/j.forsciint.2009.05.001. PMID 19500924.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ 1-[(3,4-Methylenedioxy)phenyl]-2-pyrrolidino-1-alkanones as stimulants. (Boehringer Ingelheim G.m.b.H.). Brit. (1969), 7 pp. CODEN: BRXXAA GB 1149366 19690423 Patent. Priority: DE 19650523. CAN 72:21608 AN 1970:21608 CAPLUS
  10. ^ a b c d e f http://www.deadiversion.usdoj.gov/drugs_concern/mdpv.pdf DEA report on MDPV
  11. ^ Insid
  12. ^ a b http://www.namsdl.org/documents/ACMDCathinonesReport.pdf Advisory Council on the Misuse of Drugs - Consideration of the cathinones
  13. ^ Erowid MDPV Vault : Effects
  14. ^ Strano-Rossi, Sabina; Cadwallader, Amy; De La Torre, Xavier; Botrè, Francesco (September 30, 2010). "Toxicological determination and in vitro metabolism of the designer drug methylenedioxypyrovalerone (MPDV) by gas chromatography/mass spectrometry and liquid chromatography/quadrupole time-of-flight mass spectrometry". Rapid Communications in Mass Spectrometry. 24 (18): 2706–2714. doi:10.1002/rcm.4692. PMID 20814976. Retrieved May 22, 2011.
  15. ^ Michaelis, W; (1970) "The metabolism of pyrovalerone hydrochloride". J Med Chem. 13(3): 497-503.
  16. ^ Meyer, Markus; Du, Peng; Schuster, Frank; Maurer, Hans (December 2010). "Studies on the metabolism of the α-pyrrolidinophenone designer drug methylenedioxy-pyrovalerone (MDPV) in rat and human urine and human liver microsomes using GC–MS and LC–high-resolution MS and its detectability in urine by GC–MS". Journal of Mass Spectrometry. 45 (12): 1426–1442. doi:10.1002/jms.1859.. PMID 21053377. Retrieved May 22, 2011. {{cite journal}}: Check |doi= value (help)
  17. ^ Rakow, Erica (Jan 26, 2011). "Florida makees sales and possession of bath salts illegal". WJHG-TV. Retrieved 2011-01-27.
  18. ^ Williams, Tyana (Jan 06, 2011). "Livingston deputies begin seizing "bath salts". WAFB. Retrieved 2011-01-08. {{cite news}}: Check date values in: |date= (help)
  19. ^ McConnaughey, Janet (2010-12-23). "Drugs disguised as bath salts send users to ERs". WAFB. Associated Press. Retrieved 2011-01-08.
  20. ^ Allen, Greg (February 8, 2011). "Florida Bans Cocaine-Like 'Bath Salts' Sold In Stores". NPR. Retrieved May 22, 2011.
  21. ^ Beshear, Steve. "Press Release". Gov. Beshear signs law banning new synthetic drugs. Commonwealth of Kentucky. Retrieved Wednesday, March 23, 2011. {{cite web}}: Check date values in: |accessdate= (help)
  22. ^ "New law sets fine at $350 for 'bath salts' possession". Portland Press Herald. 7 July 2011. Retrieved 7 July 2011.
  23. ^ New Jersey Department of Consumer Affairs, April 28 2011, http://docs.google.com/viewer?a=v&q=cache:-MKauNNIv6oJ:www.nj.gov/oag/newsreleases11/pr20110428a_nationwide-efforts.pdf+mdpv+legislation+nationwide&hl=en&gl=us&pid=bl&srcid=ADGEESjCrhtACHwPDLN7dRxhxoWZnf01ngG0TqyB6yV66gpncYP0oS6LRoQFdXYXEmVznOvdyB7NbwdhdUh6YFUSDaRc_KUDCvEMdW3nBFr2jOgV8fkQKDk_oCSk10s0QAt_j-_4z-NZ&sig=AHIEtbT1DTfox07hee3Q_RgeiaOAhHUvFg
  24. ^ [1]
  25. ^ [2]
  26. ^ http://state.tn.us/sos/acts/107/pub/pc0169.pdf
  27. ^ Suomen valtioneuvosto (28. June 2010). "Finlex: huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen liitteen IV muuttamisesta". Oikeusministeriö (in Finnish). Oikeusministeriö. Retrieved 25 January 2011. {{cite web}}: Check date values in: |date= (help)
  28. ^ "Hovrätten skärper straff i MDPV-dom". Norrköpings Tidningar (in Swedish). June 4, 2010. Retrieved June 12, 2010.
  29. ^ Wells, Dean (April 9. 2011). "Dead men had used bath salts". Warren Times Observer. Retrieved May 22, 2011. {{cite news}}: Check date values in: |date= (help)
  30. ^ Wilson, Todd (May 12, 2011). "Illinois lawmakers target bath salts used as a drug". Chicago Tribune. Retrieved May 22, 2011.
  31. ^ "Emergency Department Visits After Use of a Drug Sold as "Bath Salts"-Michigan, November 13, 2010-March 31, 2011", Morbidity and Mortality Weekly Report, 60 (19): 624–627, May 20, 2011
  32. ^ Oregon Health & Science University, Bath Salts Fast Facts, March 25 2011, http://www.ohsu.edu/poison/documents/FFBath_Salts.pdf?WT_rank=2
  33. ^ Salter, Jim; Suhr, Jim (April 7, 2011). "AP IMPACT: Synthetic drugs send thousands to ER". Bloomberg Businessweek. Retrieved May 22, 2011.
  34. ^ http://www.nytimes.com/2011/07/17/us/17salts.html
  35. ^ "Bath Salts Healthcare Provider Fact Sheet" (PDF). Feb 3, 2011.

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