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MPHP Powder

MPHP Powder: a designer stimulant drug

MPHP is a designer stimulant drug active on the central nervous system, written as C17H25NO. Its molar mass is 259.385 g/mol. Structurally it is related to psychostimulants and is assumed to have similar effects in humans, though it can be poisonous and fatalities associated with consumption of MPHP have been recorded. One reported injury included fractures in both feet after jumping out of a window when MPHP and amyl nitrite had been consumed. MPHP had been used as a substitute for cocaine. Other negative effects of MPHP include severe liver poisoning and rhabdomyolysis.

MPHP is in the family of chemicals called pyrrolidinophenones, which have a pyrrolidinyl group, an aryl, and a ketone with an alkyl of varying lengths (three to seven carbon atoms). These groups provide the stimulant effect. The structure of MPHP is most similar to pyrovalerone – MPHP is a homologue with a longer chain. In general, pyrrolidinophenones have the highest potency with isohexyl or pentyl backbone. The aromatic ring may have various substituents.

The patent for MPHP was awarded in 1966 to Ingelheim Boehringer under a larger group of ketones containing four specific chemical properties that are prepared through any of five different processes. These processes include:

  1. reacting a halogenoketone with an unsubstituted or alkyl-substituted pyrrolidine or morpholine
  2. reacting a nitrile with methylenedioxybenzene while using a Friedel-Crafts type catalyst to yield a ketimine, which is then hydrolyzed
  3. reacting an acid nitrile or an amine with an organo-magnesium substance and then hydrolyzing the organometallic compound
  4. reacting an a-aminoalkanol with an oxidizer (e.g. chromic acid) or an alkali metal dichromate
  5. reacting certain halogenoketones with alkali metal alkoxides to yield an expoxy ether and then reacting that expoxy ether with unsubstituted or alkyl-substituted pyrroloidine or morpholine

Any of these five methods can be converted to a non-toxic acid addition salt of the product.

MPHP is completely metabolized by rats through hydroxylation of the tolyl methyl group to 4′-hydroxymethyl-alpha-pyrrolidinohexanophenone (HO-MPHP). Similarly, it is completely metabolized by humans prior to urinary excretion, which results in difficulty detecting it for toxicological quantification. Human cytochrome P450 (CYP) isoenzymes are involved in this initial hydroxylation. Hydroxylation is followed by dehydrogenation to carboxylic acid, and hydroxylation of the side chain and the pyrrolidine ring, followed by dehydrogenation to lactam or keto reduction. The hydroxy and carboxy groups become only partially conjugated.

HO-MPHP can be synthesized for quantification by incubating MPHP-HNO3 with a fission yeast culture (Schizosaccharomyces pombe strain CAD64). This heterologously co-expresses human CYP reductase and CYP2D6. Centrifugation and solid-phase extraction followed by HPLC (high-performance liquid chromatography) enables extraction from the eluent.aa.

Detection of MPHP involves solid-phase extraction, trimethylsilylation, and gas chromatography-mass spectrometry. Using mass chromatography for screening and GC-MS, MPHP can be detected in urine based on its metabolites.

In Sweden, MPHP is classified as a narcotic.

See Also:

  • Prolintane
  • α-PBP
  • α-PPP
  • α-PVP
  • α-PHP
  • 4′-hydroxymethyl-alpha-pyrrolidinohexanophenone
  • 1-(4-Methylphenyl)-2-pyrrolidin-1-ylhexan-1-one (synonym)
  • 4′-methyl-alpha-pyrrolidinohexanophenone (synonym)
  • RS)-1-(4-methylphenyl)-2-(1-pyrrolidinyl)-1-hexanone (synonym)
  • R,S-4′-Methyl-alpha-pyrrolidinohexanophenone (synonym)