Acute poisoning involving the pyrrolidinophenone-type designer drug 4′-methyl-alpha-pyrrolidinohexanophenone (MPHP)

Sauer, Christoph; Hoffmann, Kerstin; Schimmel, Ulrich; Peters, Frank T.

doi:10.1016/j.forsciint.2011.02.026

Cited by 36 publications

(19 citation statements)

References 20 publications

(26 reference statements)

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“…In particular, a-pyrrolidinophenones, including 3,4-methylenedioxypyrovalerone (MDPV) [6,7], apyrrolidinovalerophenone (a-PVP) [8][9][10][11][12][13], a-pyrrolidinobutiophenone (a-PBP) [13][14][15], 4-methyl-a-pyrrolidinohexanophenone (MPHP) [16,17], and 3,4-methylenedioxya-pyrrolidinobutiophenone (MDPBP) [18], have rapidly become a popular class of designer drugs. 1-Phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) is an a-PVP analog in which the alkyl chain is elongated up to eight carbons, also known as a-pyrrolidinooctanophenone (a-POP).…”

Section: Introductionmentioning

confidence: 99%

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

et al. 2015

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1-Phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) and 16 metabolites, including diastereomers and conjugates, were identified or tentatively detected in human urine by gas chromatography-mass spectrometry and liquid chromatography-high-resolution tandem mass spectrometry. These urinary metabolites indicated that the metabolic pathways of PV9 include: (1) the reduction of ketone groups to their corresponding alcohols; (2) oxidation of the pyrrolidine ring to the corresponding pyrrolidone; (3) aliphatic oxidation of the terminal carbon atom to the corresponding carboxylate form, possibly through an alcohol intermediate (not detected); and (4) hydroxylation at the penultimate carbon atom to the corresponding alcohols followed by further oxidation to ketones, and combinations of these steps. In addition, results from the quantitative analyses of five phase-I metabolites using newly synthesized authentic standards suggested that the main metabolic pathway includes the aliphatic oxidation of terminal and/or penultimate carbons. Human metabolism of PV9 differed significantly from those of a-pyrrolidinovalerophenone and a-pyrrolidinobutiophenone, suggesting that the main metabolic pathways of a-pyrrolidinophenones significantly change depending on the alkyl chain length of the parent molecule.

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Section: Introductionmentioning

confidence: 99%

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

et al. 2015

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“…In a case of recreational use of naphyrone that produced acute sympathomimetic toxicity, naphyrone concentrations were 0.03 mg/L and 0.02 mg/L, 40 hours and 60 hours after drug intake, respectively 69. In a patient with signs of toxic liver damage and rhabdomyolysis followed by renal insufficiency repeatedly treated by hemodialysis, MPHP was found in serum in a concentration of approximately 0.1 mg/L 77. In a 23-year old man with a prior psychiatric history arriving via emergency medical service for bizarre behavior, suicidality, and hallucinations, serum and urine were found to contain MDPV at concentrations of 0.186 mg/L and 0.136 mg/L, respectively, and flephedrone at concentrations of 0.346 mg/L and 0.257 mg/L, respectively 78.…”

Section: Human Use Of Substituted Cathinonesmentioning

confidence: 99%

Emerging drugs of abuse: current perspectives on substituted cathinones

Paillet-Loilier¹,

Cesbron²,

Boisselier³

et al. 2014

SAR

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Substituted cathinones are synthetic analogs of cathinone that can be considered as derivatives of phenethylamines with a beta-keto group on the side chain. They appeared in the recreational drug market in the mid-2000s and now represent a large class of new popular drugs of abuse. Initially considered as legal highs, their legal status is variable by country and is rapidly changing, with government institutions encouraging their control. Some cathinones (such as diethylpropion or pyrovalerone) have been used in a medical setting and bupropion is actually indicated for smoking cessation. Substituted cathinones are widely available from internet websites, retail shops, and street dealers. They can be sold under chemical, evocative or generic names, making their identification difficult. Fortunately, analytical methods have been developed in recent years to solve this problem. Available as powders, substituted cathinones are self-administered by snorting, oral injestion, or intravenous injection. They act as central nervous system stimulants by causing the release of catecholamines (dopamine, noradrenaline, and serotonin) and blocking their reuptake in the central and peripheral nervous system. They may also decrease dopamine and serotonin transporter function as nonselective substrates or potent blockers and may inhibit monoamine oxidase effects. Nevertheless, considerable differences have been found in the potencies of the different substituted cathinones in vitro. Desired effects reported by users include increased energy, empathy, and improved libido. Cardiovascular (tachycardia, hypertension) and psychiatric/neurological signs/symptoms (agitation, seizures, paranoia, and hallucinations) are the most common adverse effects reported. Severe toxicity signs compatible with excessive serotonin activity, such as hyperthermia, metabolic acidosis, and prolonged rhabdomyolysis, have also been observed. Reinforcing potential observed in animals predicts a high potential for addiction and abuse in users. In case of overdose, no specific antidote exists and no curative treatment has been approved by health authorities. Therefore, management of acute toxic effects is mainly extrapolated from experience with cocaine/amphetamines.

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“…There are no data available for 4-MeOPBP poisonings to date, whereas several acute or fatal poisoning cases after abuse of other a-pyrrolidinophenone derivatives have been reported along with their concentrations in body samples [8][9][10][11][12][13][14][15][16]. Of these, three were 3 0 ,4 0 -methylenedioxy-a-pyrrolidinovalerophenone (MDPV) intoxication cases: one was found to have 140 ng/ml in urine on the day of admission [8], and the second had 82 ng/ml in serum and 670 ng/ml in urine at the time of arrival at a tertiary care center [9].…”

Section: Quantification Of 4-meopbp In Plasma and Urine Samplesmentioning

confidence: 99%

“…The third postmortem case reported as high as 1200 ng/ml of MDPV in cardiac blood; therefore, they concluded that the death was caused by MDPV poisoning [10]. In addition, a 4 0 -methyl-a-pyrrolidinohexiophenone (MPHP) intoxication case had 100 ng/ml in serum [11], and a-pyrrolidinovalerophenone (PVP) fatal cases had 486 ng/ml in whole heart blood [12] and 654 ng/ml in femoral vein blood [13]. In general, a-pyrrolidinophenone derivatives are more lipophilic and have a greater ability to cross the bloodbrain barrier than other synthetic cathinones because of the highly lipophilic pyrrolidine moiety [7].…”

Section: Quantification Of 4-meopbp In Plasma and Urine Samplesmentioning

confidence: 99%

Identification and quantification of 4′-methoxy-α-pyrrolidinobutiophenone (4-MeOPBP) in human plasma and urine using LC–TOF-MS in an autopsy case

et al. 2015

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We encountered an autopsy case of a 35-yearold man who drowned in a bathtub. Nine opened packages of designer drugs containing herbal blends, powders, or liquid were found at the scene, implying abuse. The plasma and urine samples of the deceased were analyzed using liquid chromatography-time-of-flight-mass spectrometry (LC-TOF-MS) with MS E . A new synthetic cathinone, 4 0 -methoxy-a-pyrrolidinobutiophenone (4-MeOPBP), emerged as a suspected component via elemental composition and molecular structure analyses with acquisition of full spectra of the precursor and product ions by MS E mode. The component was finally identified by comparing the mass spectra obtained from the deceased's samples with those of the reference standard 4-MeOPBP using LC-TOF-MS and gas chromatography-mass spectrometry. Furthermore, 4-MeOPBP was the main component of an opened package labeled ''Silver Snow''. The concentrations of 4-MeOPBP in plasma and urine samples were as high as 9.5 and 12 lg/ml, respectively. To our knowledge, this is the first report disclosing 4-MeOPBP in human specimens.

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Acute poisoning involving the pyrrolidinophenone-type designer drug 4′-methyl-alpha-pyrrolidinohexanophenone (MPHP)

Cited by 36 publications

References 20 publications

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

Urinary excretion and metabolism of the α-pyrrolidinophenone designer drug 1-phenyl-2-(pyrrolidin-1-yl)octan-1-one (PV9) in humans

Emerging drugs of abuse: current perspectives on substituted cathinones

Identification and quantification of 4′-methoxy-α-pyrrolidinobutiophenone (4-MeOPBP) in human plasma and urine using LC–TOF-MS in an autopsy case

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