5-(2-Aminopropyl)indole (5-API or5-IT),[2] also known as3,4-pyrrolo[b]amphetamine or by the code namePAL-571, is anindole andamphetamine derivative withstimulant effects.[1] Its preparation was first reported byAlbert Hofmann in 1962.[3] It is adesigner drug that has been openly sold as arecreational drug by online vendors since 2011.[4]
Alexander Shulgin wrote briefly about 5-IT inTiHKAL saying: "at 20 milligrams orally, [it] is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours."[1] As 5-IT is not a tryptamine and thus not within the scope of the book, it is not discussed in any more detail than this.
5-IT has been attributed to 14 deaths of people in Sweden since its discovery.[5][6] 5-IT was listed as the sole intoxicant in two cases but other drugs were also found in the twelve otherpost mortem examinations. The 14 deaths occurred between April and July 2012, but a definitive identification of 5-IT in the post-mortem samples was not made until July. All of the dead were young men aged between 20 and 30. Eleven non-fatal poisonings due to 5-IT also reportedly occurred during the same time period.[7]
Although 5-IT is apositional isomer of thetryptamine drugαMT, the compound is not itself a tryptamine as the indole ring is substituted at the 5 position rather than at the 3 position. The compound is closer chemically to phenethylamine derivatives such as5-APB. This is reflected in the compound's effects when used as a drug, which are reportedly stimulating rather than psychedelic. Along with αMT, it is one of the 7possible positional isomers ofaminopropylindole.[1]
5-IT is a positional isomer ofαMT (a schedule 1 controlled substance in the United States), and as such is possibly considered a schedule 1 controlled substance itself under theControlled Substances Act.[citation needed]
5-IT was banned in the UK as atemporary class drug in June 2013, along with 9 other related compounds.[12] On March 5, 2014, the UK Home Office announced that 5-API would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[13]
5-IT is covered by the Australian analogue act as an analogue ofMDA "by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures".[14]
A formal application for 5-IT to be made illegal in Sweden was made on July 26, 2012, but did not come into effect immediately.[citation needed]
5-IT was made illegal in Denmark on 30 September 2012.[citation needed]
The European Commission published a proposal for a decision calling upon its member states to take measures to control 5-(2-aminopropyl)indole. It asked member states to introduce control measures and criminal penalties as provided under their national legislation covering psychotropic substances.[15]
^Herraiz T, Brandt SD (July–August 2014). "5-(2-Aminopropyl)indole (5-IT): a psychoactive substance used for recreational purposes is an inhibitor of human monoamine oxidase (MAO)".Drug Testing and Analysis.6 (7–8):607–613.doi:10.1002/dta.1530.hdl:10261/102667.PMID24115740.
^Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR (April 2017). "In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks".Toxicol Lett.272:84–93.doi:10.1016/j.toxlet.2017.03.007.PMID28302559.
^Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME (May 2018). "Pharmacological profile of mephedrone analogs and related new psychoactive substances".Neuropharmacology.134 (Pt A):4–12.doi:10.1016/j.neuropharm.2017.07.026.PMID28755886.
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