Adverse Effects of the Use of Unusual Phenethylamine Compounds Sold as Illicit Amphetamine

Bal, T.S.; Gutteridge, Daniel; Johnson, Bruce M.; Forrest, A.R.W.

doi:10.1177/002580248902900303

Cited by 13 publications

(5 citation statements)

References 2 publications

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“…The described side effects in this report were mydriasis, hyperthermia, hypertension, tachycardia, insomnia, and anxiety. 39 These effects are in accordance with the described effects in other case and trip reports.…”

Section: Methylphenyl-amphetaminessupporting

confidence: 91%

“…The suggested reasons for such deaths was on the one hand the increased serotonergic effects of 4-MA compared with amphetamine and on the other hand redosing due to underestimated onset or the dampened psychoactive effect when using 4-MA together with amphetamine. A trip report published by Bal et al in 1989 showed that 4-MA together with its N-methyl derivative has already been sold as amphetamine in the past. The described side effects in this report were mydriasis, hyperthermia, hypertension, tachycardia, insomnia, and anxiety.…”

Section: Methylphenyl-amphetaminesmentioning

confidence: 99%

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New Psychoactive Substances

Welter‐Luedeke

Maurer

2016

Therapeutic Drug Monitoring

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In recent years, new amphetamine derivatives with modified ring systems were sold and consumed as new drugs of abuse. They belong together with other new drugs of abuse classes to the so-called new psychoactive substances (NPS). The chemistry, pharmacology, toxicology, metabolism, and toxicokinetics are shortly discussed of camfetamine, 3 methylphenyl-amphetamines (2-MA, 3-MA, and 4-MA), 2-methiopropamine (2-MPA), and 5-(2-aminopropyl)benzofuran (5-APB), 6-(2-aminopropyl)benzofuran (6-APB, so-called "benzofury") and their N-methyl derivatives 5-MAPB and 6-MAPB. Only a rough assessment of the pharmacology and toxicology NPS can be performed in most cases using published data of analogs, trip reports, and described clinical cases. Accordingly, they all act more or less as central nervous stimulants mainly by increasing the concentration of the neurotransmitters noradrenaline, dopamine, and serotonin (5-HT) by inducing their release and reuptake inhibition. Thus, the acute toxicity is associated with the sympathomimetic effects, such as mydriasis, hyperthermia, hypertension, tachycardia, insomnia, and anxiety. With the exception of 5- and 6-APB, these NPS were extensively metabolized by N-demethylation and/or aromatic hydroxylation catalyzed by various cytochrome P450 isoenzymes followed by partial glucuronidation and/or sulfation. For urinalysis, the unchanged drugs and/or the nor-metabolites are the main targets.

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Section: Methylphenyl-amphetaminessupporting

confidence: 91%

Section: Methylphenyl-amphetaminesmentioning

confidence: 99%

New Psychoactive Substances

Welter‐Luedeke

Maurer

2016

Therapeutic Drug Monitoring

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“…Some may view this as an unnecessary approach for casework; however, a counterexample is the recent BALCO scandal where spectral interpretation of MS‐derived data was pivotal in determining the parent structure of the synthetic steroid tetrahydrogestrinone (THG) (16–19). Another example of the importance of mass spectral analysis is a case in which ring‐substituted amphetamine (para methyl—a regioisomer of compound VIII synthesized in this study) and p ‐methyl ring‐substituted methamphetamine sold as amphetamine caused an adverse reaction in a seasoned amphetamine user (20). The approach of the laboratory to determine the culprit molecule was identification by GC/MS, followed by “analysis of authentic samples of p ‐methyl(meth)amphetamine prepared in the laboratory.” Thus, it is not an unprecedented use of the tools of the forensic laboratory to use deconstructive fragmentation analysis of related compounds, followed by predictions of fragmentation and then synthesis of a compound to confirm the predictions.…”

mentioning

confidence: 99%

A Detailed Mechanistic Fragmentation Analysis of Methamphetamine and Select Regioisomers by GC/MS

Sachs

Woo

2007

Journal of Forensic Sciences

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A novel ring-substituted methamphetamine regioisomer, N,alpha,4-trimethyl phenmethylamine, was synthesized in order to study the validity of proposed structures for various mass spectrometry (MS)-derived peaks in a methamphetamine fragmentation pattern. While other research efforts have studied aspects of methamphetamine in detail, a full fragmentation study has not been reported previously. In addition to showing molecular structures represented by fragment peaks, mechanisms for selected processes are detailed. An empirically derived procedure to easily determine by simple spectral peak pattern recognition the geometry of dimethyl- or ethyl-substituted immonium ions (RRC = N+ RR) where m/z = 58 is outlined. These results are platform independent for electron ionization (EI) instruments, but have also proven to be helpful in explaining spectral peaks observed in spectra from ion trap systems. The spectrum for the synthesized methamphetamine regioisomer was accurately predicted using this methodology. While this approach is useful in some casework, the converse may be more useful: when an unexpected or unusual peak pattern arises in a spectrum, being able to analyze it to determine the structure of the molecule. This paper gives an analyst the means to begin such retro-synthetic analyses.

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“…In this regard, it was described a massive adrenergic overstimulation just after inhaling material, which had been purchased in the belief that it was amphetamine but also contained 4-MA and dimethyl-amphetamine [3]. Only in one case, a patient with forensic evidence of 4-MA, developed extreme hyperthermia and died after cardiac arrest, although he had consumed ketamine, cocaine and other amphetamines 24 h before (EMCDDA-Europol report 2012).…”

Section: Introductionmentioning

confidence: 99%

Serotonin is involved in the psychostimulant and hypothermic effect of 4-methylamphetamine in rats

Rubio

López-Arnau

Piccoli

et al. 2015

Neuroscience Letters

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Abstract4-methylamphetamine (4-MA) has recently emerged as a designer drug of abuse in Europe and it is consumed always with amphetamine. There have been reported some deaths and non-fatal intoxications related to 4-MA. We investigated the changes in locomotor activity and body temperature after 4-MA administration to male SpragueDawley rats. Our experiments were carried out at a normal or high ambient temperature. 4-MA (2.5 -10 mg/Kg, given subcutaneously) increased, in a dosedependent manner, the horizontal locomotor activity that was significantly reduced by ketanserin, p-cholorophenylalanine (pCPA) or haloperidol. In addition, we have studied the effect of 4-MA on core body temperature by means of an implanted electronic thermograph, enabling continuous measurement of body temperature. We observed a dose-dependent hypothermic response to 4-MA that reached a maximum 45 min after a single injection. We also evidenced slight tachyphylaxis to the hypothermic effect when 4-MA was administered four times in a 2 h interval. The pre-treatment of animals with pCPA or pindolol, but not with ketanserin, fully abolished the hypothermic effect of 4-MA. With all that, we conclude that hypothermia induced by 4-MA is due to the release of 5-HT which activates postsynaptic 5-HT 1A receptors.

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Adverse Effects of the Use of Unusual Phenethylamine Compounds Sold as Illicit Amphetamine

Cited by 13 publications

References 2 publications

New Psychoactive Substances

New Psychoactive Substances

A Detailed Mechanistic Fragmentation Analysis of Methamphetamine and Select Regioisomers by GC/MS

Serotonin is involved in the psychostimulant and hypothermic effect of 4-methylamphetamine in rats

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