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'''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, Super Coke and PV.<ref name="194.83.136.209">http://194.83.136.209/documents/reports/MDPV.pdf. MDPV report, Psychonaut Research Web Mapping Project</ref> 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).<ref>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 (drug)|Spice]] and [[K2 (drug)|K2]] as incense.</ref><ref>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.</ref> Media warnings and law enforcement officials refer to it as a "dangerous but legal drug", "copy-cat cocaine", "the devil", "poison", and "synthetic speed".<ref>{{cite news|accessdate=16 May 2011|url=http://www.nbc33tv.com/consumer-alert/parents-cautioned-against-over-the-counter-synthetic-speed|title=Parents cautioned against over the counter synthetic speed|date=9 November 2010|publisher=NBC 33 News |author=News Desk Manager, Samantha Morgan|work=}}</ref><ref>{{cite news|accessdate=16 May 2011|url=http://www.nbc33tv.com/news/bath-salts-used-to-get-high|title=Bath Salts Used to Get High|date=6 January 2011|publisher=NBC 33 News |author=Kelsey Scram|work=}}</ref>
'''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, Super Coke and PV.<ref name="194.83.136.209">http://194.83.136.209/documents/reports/MDPV.pdf. MDPV report, Psychonaut Research Web Mapping Project</ref> 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, White Height Chaser, Vanilla Sky, White Dove, White Girl, White Lightning).<ref>http://bathsalt4us.com</ref><ref>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 (drug)|Spice]] and [[K2 (drug)|K2]] as incense.</ref><ref>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.</ref> Media warnings and law enforcement officials refer to it as a "dangerous but legal drug", "copy-cat cocaine", "the devil", "poison", and "synthetic speed".<ref>{{cite news|accessdate=16 May 2011|url=http://www.nbc33tv.com/consumer-alert/parents-cautioned-against-over-the-counter-synthetic-speed|title=Parents cautioned against over the counter synthetic speed|date=9 November 2010|publisher=NBC 33 News |author=News Desk Manager, Samantha Morgan|work=}}</ref><ref>{{cite news|accessdate=16 May 2011|url=http://www.nbc33tv.com/news/bath-salts-used-to-get-high|title=Bath Salts Used to Get High|date=6 January 2011|publisher=NBC 33 News |author=Kelsey Scram|work=}}</ref>




Revision as of 23:42, 15 June 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)

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, 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, White Height Chaser, Vanilla Sky, White Dove, White Girl, White Lightning).[2][3][4] Media warnings and law enforcement officials refer to it as a "dangerous but legal drug", "copy-cat cocaine", "the devil", "poison", and "synthetic speed".[5][6]


Appearance

The substance appears as a pure white to light-brown hygroscopic, clumpy powder with a slight odor. It appears to darken slightly in color and take on a potato-tuber-like odor if exposed to air for any significant length of time. In some of the first batches that appeared on the research chemical market, an impurity was identified and said to consist of pyrrolidine, which could account for its earthy odor when left uncapped. It has also been observed to rapidly degrade and change properties when in exposed to air as a free base.[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) and 3',4'-methylenedioxy-α-pyrrolidinopropiophenone (MDPPP).

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 effects

Desired psychological effects

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][11] 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:[12]

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.)

Chemistry

The best synthetic route probably involves the 4-step alkylation-oxidation-bromination-amination methodology.[13] One possible preparation involves alkylation of piperonal in a Grignard reaction using n-butylmagnesium bromide or 1-bromobutane and magnesium metal in diethyl ether, and under anhydrous conditions using an inert atmosphere such as nitrogen. The second step involves oxidation of the resulting alcohol back into a ketone by adding it (without the ether phase) to a suspension of pyridinium chlorochromate in chloroform. The use of an optional organometallic scavenger such as nano-porous silica gel will make workup easier. After workup and redissolving residue in fresh chloroform, third-step addition of bromine will create a dibrominated haloketone with two bromide atoms at the alpha position, and acts as the leaving group during subsequent (fourth-step) amination with pyrrolidine in ether, which should take 12 hours and proceed at room temperature (20°C). Workup; Several washes with cold water, keeping the ethereal phase, will draw off most of the excess pyrollidine. Dissolve in absolute ethanol and salt with HCl. Recrystallize from a mixture of ethanol and ether. M.P. 229-231°C[14]

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.[15] No free pyrrolidine will be detected in the urine.[16]

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.[17]

Legality

In the UK, following the ACMD's report on cathinone derivatives,[11] 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[18]), but began appearing on the media radar in early 2011.[19][20][21] 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. [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]

MDPV is specifically listed as a controlled substance in Finland (listed appendix IV substance as of 28 June 2010),[24] 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.[25] In Germany it does fall under the BtMG Anlage II since 06.12.2010 which makes it illegal to manufacture, sell or import without a license. [26]

On April 27, 2011 the New Jersey Division of Consumer Affairs made it "a crime to manufacture, distribute, sell, or possess designer drugs labeled as 'bath salts'"[27]

Deaths

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.[28] In April 2011, an Alton, Illinois woman apparently died from an MPDV overdose.[29] 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.[30]

Toxicology results show that a Spanaway, Washington soldier who killed his son earlier that day, then his wife and himself in April of 2011 as he was being pursued by troopers had a chemical in his system that's associated with a highly potent designer drug.[31]

In June 2011, a Spanaway, WA couple sped past a trooper on I-5, when the officer followed, the man killed his wife and himself. Bath salt was found in his pocket, in his car and spilled onto the road. Their son was later found, with a bag over his head and bruises on his body. Police say bath salt was directly related.[32]

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.[33]According to the California Poison Action Line, a person who may have taken MDPV or other dangerous substance is urged to follow treatment steps including: keep calm; call your local medical emergency phone number (dial 9-1-1 in US) for unconscious, convulsions or difficulty breathing. Otherwise, call the poison control center. [34] 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.[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://bathsalt4us.com
  3. ^ 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.
  4. ^ 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.
  5. ^ News Desk Manager, Samantha Morgan (9 November 2010). "Parents cautioned against over the counter synthetic speed". NBC 33 News. Retrieved 16 May 2011.
  6. ^ Kelsey Scram (6 January 2011). "Bath Salts Used to Get High". NBC 33 News. Retrieved 16 May 2011.
  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. ^ a b http://www.namsdl.org/documents/ACMDCathinonesReport.pdf Advisory Council on the Misuse of Drugs - Consideration of the cathinones
  12. ^ Erowid MDPV Vault : Effects
  13. ^ Loo, P; 2010 Jun. 3. "Convenient Synthesis and Spectroscopic Data of Methcathinone Analogs". 4th Seminar of European Customs Chemists..
  14. ^ Koppe H, Ludwig G, Karl Z; 1969 Nov. 11. 1-(3',4'-METHYLENEDIOXY-PHENYL)-2-PYRROLIDINO-ALKANONES-(1). United States Patent 3,478,050.
  15. ^ 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.
  16. ^ Michaelis, W; (1970) "The metabolism of pyrovalerone hydrochloride". J Med Chem. 13(3): 497-503.
  17. ^ 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)
  18. ^ Rakow, Erica (Jan 26, 2011). "Florida makees sales and possession of bath salts illegal". WJHG-TV. Retrieved 2011-01-27.
  19. ^ Williams, Tyana (Jan 06, 2011). "Livingston deputies begin seizing "bath salts". WAFB. Retrieved 2011-01-08. {{cite news}}: Check date values in: |date= (help)
  20. ^ McConnaughey, Janet (2010-12-23). "Drugs disguised as bath salts send users to ERs". WAFB. Associated Press. Retrieved 2011-01-08.
  21. ^ Allen, Greg (February 8, 2011). "Florida Bans Cocaine-Like 'Bath Salts' Sold In Stores". NPR. Retrieved May 22, 2011.
  22. ^ 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)
  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. ^ 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)
  25. ^ "Hovrätten skärper straff i MDPV-dom". Norrköpings Tidningar (in Swedish). June 4, 2010. Retrieved June 12, 2010.
  26. ^ [1] 36. Sitzung des Sachverständigenausschusses nach § 1 Abs. 2 des Betäubungsmittelgesetzes (BtMG) am 06. Dezember 2010 um 13.00 Uhr im Bundesinstitut für Arzneimittel und Medizinprodukte (BfArM, Bonn)
  27. ^ [2]
  28. ^ 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)
  29. ^ Wilson, Todd (May 12, 2011). "Illinois lawmakers target bath salts used as a drug". Chicago Tribune. Retrieved May 22, 2011.
  30. ^ "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
  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. ^ http://www.komonews.com/news/local/123779009.html
  33. ^ Oregon Health & Science University, Bath Salts Fast Facts, March 25 2011, http://www.ohsu.edu/poison/documents/FFBath_Salts.pdf?WT_rank=2
  34. ^ California Poison Control System, accessed May 13, 2011, http://www.calpoison.org/public/eaction.html
  35. ^ Salter, Jim; Suhr, Jim (April 7, 2011). "AP IMPACT: Synthetic drugs send thousands to ER". Bloomberg Businessweek. Retrieved May 22, 2011.

External links

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