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Neuropharmacology of Synthetic Cathinones

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New Psychoactive Substances

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 252))

Abstract

Synthetic cathinones are derivatives of the naturally occurring compound cathinone, the main psychoactive ingredient in the khat plant Catha edulis. Cathinone is the β-keto analog of amphetamine, and all synthetic cathinones display a β-keto moiety in their structure. Several synthetic cathinones are widely prescribed medications (e.g., bupropion, Wellbutrin®), while others are problematic drugs of abuse (e.g., 4-methylmethcathinone, mephedrone). Similar to amphetamines, synthetic cathinones are psychomotor stimulants that exert their effects by impairing the normal function of plasma membrane transporters for dopamine (DAT), norepinephrine (NET), and 5-HT (SERT). Ring-substituted cathinones like mephedrone are transporter substrates that evoke neurotransmitter release by reversing the normal direction of transporter flux (i.e., releasers), whereas pyrrolidine-containing cathinones like 3,4-methylenedioxypyrovalerone (MDPV) are potent transporter inhibitors that block neurotransmitter uptake (i.e., blockers). Regardless of molecular mechanism, all synthetic cathinones increase extracellular monoamine concentrations in the brain, thereby enhancing cell-to-cell monoamine signaling. Here, we briefly review the mechanisms of action, structure-activity relationships, and in vivo pharmacology of synthetic cathinones. Overall, the findings show that certain synthetic cathinones are powerful drugs of abuse that could pose significant risk to users.

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Abbreviations

4-Bromo MCAT:

1-(4-Bromophenyl)-2-(methylamino)propan-1-one (brephedrone)

4-Chloro MCAT:

1-(4-Chlorophenyl)-2-(methylamino)propan-1-one (clephedrone)

4-Fluoro MCAT:

1-(4-Fluorophenyl)-2-(methylamino)propan-1-one (flephedrone)

4-Methyl MCAT (4-MMC):

2-(Methylamino)-1-(4-methylphenyl)propan-1-one (mephedrone)

4-Methoxy MCAT:

1-(4-Methoxyphenyl)-2-(methylamino)propan-1-one (methedrone)

4-TFM MCAT:

2-(Methylamino)-1-[4-(trifluoromethyl)phenyl]propan-1-one

MCAT:

2-(Methylamino)-1-phenylpropan-1-one (methcathinone)

MDMA:

1-(2H-1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine

MDMC:

1-(2H-1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one (methylone)

MDPV:

1-(2H-1,3-Benzodioxol-5-yl)-2-(pyrrolidin-1-yl)pentan-1-one

α-PBP:

1-Phenyl-2-(pyrrolidin-1-yl)butan-1-one

α-PHP:

1-Phenyl-2-(pyrrolidin-1-yl)hexan-1-one

α-PPP:

1-Phenyl-2-(pyrrolidin-1-yl)propan-1-one

α-PVP:

1-Phenyl-2-(pyrrolidin-1-yl)pentan-1-one

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Acknowledgments

The research program of Dr. Baumann is generously supported by the Intramural Research Program of the National Institute on Drug Abuse, National Institutes of Health, grant DA00523.

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Authors and Affiliations

  1. Designer Drug Research Unit (DDRU) NIDA, IRP, NIH, Baltimore, MD, USA

    Michael H. Baumann

  2. Developmental, Cognitive and Behavioral Neuroscience, University of Houston, Houston, TX, USA

    Hailey M. Walters

  3. Center for Physiology and Pharmacology, Medical University of Vienna, Vienna, Austria

    Marco Niello & Harald H. Sitte

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  1. Michael H. Baumann
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  2. Hailey M. Walters
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  4. Harald H. Sitte
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Correspondence to Michael H. Baumann .

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  1. Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, Saarland University, Homburg (Saar), Germany

    Hans H. Maurer

  2. School of Pharmacy & Biomolecular Sciences, Liverpool John Moores University, Liverpool, UK

    Simon D. Brandt

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Baumann, M.H., Walters, H.M., Niello, M., Sitte, H.H. (2018). Neuropharmacology of Synthetic Cathinones. In: Maurer, H., Brandt, S. (eds) New Psychoactive Substances . Handbook of Experimental Pharmacology, vol 252. Springer, Cham. https://doi.org/10.1007/164_2018_178

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