Methylenedioxypyrovalerone(MDPV)

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    Charles Darwin

    Charles Darwin Guest

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    Methylenedioxypyrovalerone(MDPV)

    is a
    with
    properties which acts as a
    (NDRI). It was first developed in the 1960s by a team at Boehringer Ingelheim. MDPV remained an obscure stimulant until around 2004 when it was reportedly sold as a
    . Products labeled as
    containing MDPV were previously sold as recreational drugs in gas stations and convenience stores in the
    , similar to the marketing for
    and
    as incense.

    Incidents of psychological and physical harm have been attributed to MDPV use.

    Appearance

    The hydrochloride salt exists as a very fine,
    , 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
    or alpha-dibrominated alkylphenones from either excess pyrrolidine or incomplete amination, respectively, 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.

    Pharmacology

    Methylenedioxypyrovalerone has no record of FDA approved
    .Reportedly, it has four times the
    of
    (Ritalin, Concerta), although its pharmacology has only recently been studied in detail. MDPV 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 had been carried out.

    MDPV is the 3,4-
    -
    of the compound
    , developed in the 1960s, which has been used for the treatment of chronic fatigue and as an
    , but caused problems of abuse and dependence. However, despite its
    similarity, the effects of MDPV bear little resemblance to other
    derivatives such as
    (MDMA), instead producing primarily
    effects with only mild
    qualities.

    Other drugs with a similar chemical structure include
    (α-PPP),
    (M-α-PPP),
    (MDPPP) and
    (α-PVP).

    Effects

    This sectionneeds more
    for
    or relies too heavily on primary sources    .Please review the contents of the section and
    if you can. Unsourced or poorly sourced material may be
    .(April 2012)

    MDPV acts as a
    and has been reported to produce effects similar to those of
    ,
    , and the
    . The acute effects may include:

    Desired psychological effects
    Description of effects

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

    Reported modalities of intake include oral consumption,
    ,
    ,
    and
    use. It is supposedly active at 3–5 mg, with typical doses ranging between 5–20 mg.

    Chemistry

    MDPV can be prepared by modifying the alkylation-oxidation-bromination-amination route to
    analogs. This involves a
    of
    ,
    ,
    of the aromatic ketone with
    , and subsequent
    with
    .

    The
    -di
    or
    -mono-
    intermediate from the 3rd step
    , and left behind by an expedited or incomplete final workup is the most likely contaminant/impurity to be seen in the final product using this method. Bromination is likely to in excess, since excess
    amine will form a black precipitate that is difficult to separate.

    Such
    are of particular concern to
    macro-biological organisms, and special consideration must be made when preparing MDPV for purposes of long-term
    on lab animals, especially in mammals, and especially where the possibility exists for diversion and subsequent ingestion by humans for recreational purposes. Preparation for biological purposes and testing must ensure a complete and thorough
    , including several washes with saturated
    solution after washing with water to remove the brominated intermediates before final salting of the
    for
    . Aside from the bromine ion being highly
    and reactive, the
    -
    compounds often being
    agents, and brominated aromatic derivatives being implicated as
    , there also exists the mechanism for bromine substituting for the methyl group in the
    of
    , creating the base-analog
    , which can be incorporated into DNA and induce a
    .}

    Metabolism

    MDPV undergoes
    ,
    ,
    , and
    phase 1 metabolism (liver) into
    and
    , which in turn are glucuronated (
    ) allowing it to be excreted by the kidneys, with only a small fraction of the metabolites being excreted into the stools. No free pyrrolidine will be detected in the urine.

    Molecularly, this is seen as demethylenation of methylenedioxypyrovalerone (
    ), followed by
    of the aromatic ring via
    . Then
    of both the aromatic ring and side chain takes place followed by and oxidation of the
    ring to the corresponding
    , with subsequent detachment and ring opening to the corresponding
    .

    Detection in biological specimens

    MDPV may be quantitated 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 Dead 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 overdosage.

    Overdose treatment

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

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

    Alternatively, the antihypertensive drug
    can be used to treat symptoms of MDPV intoxication.
    has been used cliniCally in the treatment of acute stimulant intoxication and withdrawal, and is sometimes prescribed to reduce the side effects of stimulant medications used to treat ADHD. Some users of MDPV have reported a reduction in the severity of symptoms upon treatment with
    .
     
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    Charles Darwin, 3. Mai 2014
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