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Methylenedioxypyrovalerone

Clinical data
Routes of administration	Oral, Insufflation, Intravenous, Rectal, Vaporization
Legal status
Legal status	Unscheduled (illegal in Denmark and Sweden)
Pharmacokinetic data
Elimination half-life	3 to 5 hours
Identifiers
IUPAC name (RS)-1-(benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one
CAS Number	687603-66-3 24622-62-6 (HCl)
PubChem CID	20111961
CompTox Dashboard (EPA)	DTXSID90897461
Chemical and physical data
Formula	C16H21NO3
Molar mass	275.35 g/mol g·mol

Methylenedioxypyrovalerone (MDPV) is a psychoactive drug with stimulant properties which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI), reportedly with four times the potency of methylphenidate (Ritalin, Concerta). MDPV has no history of FDA approved medical use but has been sold since around 2007 as a research chemical.

Appearance

The substance appears as a pure white to light-brown, significantly hydrophilic crumbly powder with a slight odour. It appears to darken slightly in colour 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 odour when left uncapped. It has also been observed to rapidly degrade and lose potency when in solution.

Effects

MDPV acts as a stimulant. The acute effects may include:

• physical: rapid heartbeat, increase in blood pressure, vasoconstriction, sweating
• mental: increases in alertness & awareness, increased wakefulness and arousal, anxiety, agitation, perception of a diminished requirement for food and sleep.

The 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. High doses have been observed to cause intense, prolonged panic attacks in stimulant-intolerant users, and there are anecdotal reports of psychosis from sleep withdrawal and addiction at higher doses or more frequent dosing intervals. MDPV has been remarked about more than once for its powers as an aphrodisiac, which have been said to rival those of methamphetamine when dosed correctly. Users often report to feel compelled to continue redosing but then lose interest in taking it quickly because of the unpleasant side effects caused by higher doses.

MDPV is the 3,4-methylenedioxy ring-substituted analogue of the anorectic or appetite suppressant pyrovalerone. 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 purely stimulant effects with no entactogenic qualities. Extended binges on MDPV have also been reported to produce severe comedown syndrome similar to that of methamphetamine, characterized by depression, lethargy, headache, anxiety, postural hypotension (lightheadedness and weakness of the muscles), and in some cases severely bloodshot eyes. Time is the solution for these symptoms, which usually subside within 4 to 8 hours. Abdominal pain consistent with kidney pain has also been reported when MDPV is used for extended periods of time. MDPV may also cause temporary trismus and/or bruxism. Side effects are highly dose-dependant.

Legality

In the UK, following the ACMD's report on cathinone derivatives, 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.

MDPV is not specifically listed as a controlled substance in any other countries besides Denmark and Sweden.

Other drugs with a similar chemical structure include α-pyrrolidinopropiophenone (α-PPP), which has a shorter alkyl chain and no ring substitution, pyrovalerone, which has a 4'-methyl group instead of a methylenedioxy ring, as well as analogues with between 3 and 6 carbons on the alkyl chain.

These compounds have been reported as stimulants of abuse mainly in Germany and other European countries since the early 2000s, but they have remained generally vaguely known and rarely used illicitly or encountered by law enforcement.

In March 2010, in an interview appearing in the Finnish-language newspaper , Helsingin Sanomat, the head of the Department of Forensic Medicine at the University of Helsinki, claimed that high levels of MDPV had been found during autopsies of several "drug users."

References

1. 1--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
2. 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)
3. MDPV Experience Report(s) - Drugs Forum
4. ACMD report on the consideration of the cathinones, Home Office 31.03.2010
5. Meltzer, Peter C.; Butler, David; Deschamps, Jeffrey R.; Madras, Bertha 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: 1420. doi:10.1021/jm050797a. {{cite journal}}: no-break space character in |title= at position 76 (help)
6. Springer, D; Fritschi, G; Maurer, HH (2003). "Metabolism of the new designer drug alpha-pyrrolidinopropiophenone (PPP) and the toxicological detection of PPP and 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP) studied in rat urine using gas chromatography-mass spectrometry". Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 796 (2): 253–66. PMID 14581066.
7. Interview with head of the Department of Forensic Medicine at the University of Helsinki, Helsingin Sanomat 16.3.2010

External links

• Pubchem - similar compounds
• J. Med. Chem Article on pubmed
• Erowid MDPV Vault

• Cathinones
• Dopamine reuptake inhibitors
• Norepinephrine reuptake inhibitors
• Pyrrolidinophenones
• Benzodioxoles