Methylenedioxypyrovalerone
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| Routes of administration | Oral, insufflation, intravenous |
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| Elimination half-life | 3 to 5 hours [citation needed] |
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| Formula | C16H21NO3 |
| Molar mass | 275.35 g/mol g·mol−1 |
Methylenedioxypyrovalerone (MDPV) is a psychoactive drug with stimulant and aphrodisiac properties which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI), reportedly with four times the potency of methylphenidate (Ritalin, Concerta).[1] MDPV has no history of FDA approved medical use but has been sold since around 2007 as a designer drug.[2]
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
The main physical effect is stimulation with typical signs such as rapid heartbeat, vasoconstriction and sweating. Mental effects may include euphoria, hypersexuality, agitation and anxiety, some degree of paranoia, and insomnia. The effects have a duration of roughly three to four hours, with after effects such as tachycardia, hypertension, and mild stimulation lasting from six to eight 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 four to eight hours. Abdominal pain consistent with kidney pain has also been reported when MDPV is used for extended periods of time.[3] MDPV may also cause temporary trismus and/or bruxism.
Legality
MDPV is not specifically listed as a controlled substance in any country besides Denmark and Sweden(from february 2010). Some people have claimed that because MDPV is most closely related in molecular structure to a Schedule V drug (Pyrovalerone) in the US, it is not controlled by the Federal Analog Act.[citation needed] The law requires it to be an "analog" that is "substantially similar" to that of a Schedule I or II drug and intended for human consumption. There are no legal cases currently known of in the USA concerning MDPV. Prosecutors in a federal US court may claim MDPV is an analog of MDMA under the Federal Analog Act, although they could not claim it is an analog of Pyrovalerone since it is not a Schedule I or II controlled substance. The prosecution could be difficult however, because MDPV has a pentyl side chain where MDMA has a propyl side chain, MDPV a beta-ketone group where MDMA has two hydrogen atoms, and a pyrrolidine, cyclic, tertiary amine where MDMA has a simpler methylamino group, a primary amine. This distinction between primary amines and tertiary amines was a major determining factor in the decision that AET was not an analog of DMT or DET in the first case prosecuted under the Federal Analog Act. In its effects, MDPV is quite dissimilar to MDMA, with MDPV being a DA/NA reuptake inhibitor rather than a releaser, and MDPV apparently lacking the strong serotonergic activity of MDMA. It would probably be extremely difficult to find an expert witness willing to testify for its prosecution.
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.[4]
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.[5]
No deaths or injuries caused by this substance have been reported.
See also
- Pyrovalerone (Centroton, Thymergix)
- Prolintane (Promotil, Katovit)
- Naphyrone (O-2482)
References
- ^ 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 written in English. Priority: DE 19650523. CAN 72:21608 AN 1970:21608 CAPLUS
- ^ 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. doi:10.1016/j.forsciint.2009.05.001. PMID 19500924.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ MDPV Experience Report(s) - Drugs Forum
- ^ Meltzer PC, Butler D, Deschamps JR, Madras BK. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) analogues: a promising class of monoamine uptake inhibitors. Journal of Medicinal Chemistry. 2006 Feb 23;49(4):1420-32.
- ^ Springer D, Fritschi G, Maurer HH. 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 Life Sciences. 2003 Nov 5;796(2):253-66.