Synthetic Aminoindanes: A Summary of Existing Knowledge.

Nikola Pinterova,Tomas Palenicek,Rachel R Horsley

doi:10.3389/fpsyt.2017.00236

Abstract

Aminoindanes ("bath salts," a class of novel psychoactive substances, NPSs) increased rapidly in popularity on the recreational drug market, particularly after mephedrone and other synthetic cathinones were banned in the UK in 2010. Novel aminoindanes continue to emerge, but relatively little is known about their effects and risks. Their history, chemistry, pharmacology, behavioral effects, pharmacokinetics, and toxicity are reviewed in this paper. Scientific literature was searched on ISI Web of Knowledge: Web of Science (WoS) during June and July 2017, using English language terms: aminoindanes such as 5,6-methylenedioxy-2-aminoindane (MDAI), 5-iodo-2-aminoindane (5-IAI), 2-aminoindane (2-AI), 5,6-methylenedioxy-N-methyl-2-aminoindane (MDMAI), and 5-methoxy-6-methyl-2-aminoindane (MMAI). WoS was selected as it searches several databases simultaneously and has quality criteria for inclusion. For typical use and effects, Erowid, PsychonautWiki, Bluelight, and Drugs-Forum were searched; for legal status and epidemiology, the European Information System and Database on New Drugs (EDND) was used. Aminoindanes were first synthesized for medical use, e.g., as anti-Parkinsonian drugs and later as a potential compound facilitating psychotherapy; however, they are now widely substituted for ecstasy. Their mechanisms of action (primarily via serotonin) mean that they may pose a significant risk of serotonin syndrome at high doses or when combined with other drugs. Fatally toxic effects have been observed both in the laboratory in animal studies and in clinic, where deaths related with aminoindanes have been reported. Greater knowledge about aminoindanes is urgently required to decrease risks of fatal intoxication, and appropriate legislation is needed to protect public health without impeding research.

Highlights

There has been a dramatic increase in the number and variety of novel psychoactive substances (NPSs) available on the illicit and gray drug markets
The paper summarizes the history of their creation, therapeutic potential in medical research and subsequent discovery by recreational drug users, their pharmacology, behavioral effects, pharmacokinetics, and toxicity
NPSs synthesized from the substances listed above are MDAI, MDMAI, MMAI, and 5-IAI (Table 1); all of these are psychoactive and their presence on the market has been confirmed in confiscated samples of “legal highs” [14]

Summary

Introduction

There has been a dramatic increase in the number and variety of novel psychoactive substances (NPSs) available on the illicit and gray drug markets ( via the Internet and “dark web”). One of the first NPSs that became widely used recreationally was the cathinone derivative mephedrone (4-MMC, 4-methylmethcathinone), marketed at the time as a “legal” substitute for ecstasy (MDMA, 3,4-methylenedioxymethamphetamine) and cocaine, sharing effects of both [2]. One of the first was 5,6-methylenedioxy-2-aminoindane (MDAI), which claimed to be a “legal,” non-neurotoxic analog of MDMA, with strong empathogenic and weaker stimulatory effects [5]. Aminoindanes such as MDAI, 5,6-methylenedioxy-N-methyl2-aminoindane (MDMAI), 5-iodo-2-aminoindane (5-IAI), 2-aminoindane (2-AI), 5-methoxy-6-methyl-2-aminoindane (MMAI), and 5-methoxy-2-aminoindane (MEAI) represent a relatively new generation of NPS. The paper summarizes the history of their creation, therapeutic potential in medical research and subsequent discovery by recreational drug users, their pharmacology, behavioral effects, pharmacokinetics, and toxicity

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