Chapter 11 – Aminoindane Analogues

One of the less well known compound classes of the so-called novel psychoactive substances are represented by analogues and derivatives that are based on the 2-aminoindane nucleus, which due to its structure, is a conformationally rigid analogue of amphetamine. Published animal and in vitro studies of the pharmacological profile of various aminoindanes indicate an involvement of serotonin release and re-uptake. In addition, drug discrimination studies carried out in rats pointed towards some pharmacological properties that are also shared with 3,4-methylenedioxymethamphetamine (MDMA). At first glance, one might be tempted to consider whether such substances would display empathogenic or entactogenic effects similar to MDMA and/or whether drug users might consider these substances as potential MDMA-replacements, particularly those on the lookout for substances that are not under control in most countries. At present there is very limited information about the acute and chronic human toxicity of various aminoindane derivatives, with the extent of current availability and trends in recreational use of this class of drugs being uncertain. However, from a clinical and forensic toxicology perspective, it is important to be able to identify the possible presence of such compounds and their potential metabolites in biological fluids and tissues, also to follow any trend in their use and need for control measures to be introduced. This chapter will provide an account of selected aminoindanes regarding their chemistry, pharmacology and toxicology and concludes that, so far, aminoindanes appear to play a minor role.