:5-(2-Aminopropyl)indole

Although 5-IT is a positional isomer of the tryptamine drug αMT, 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 as 5-APB. This is reflected in the compound's effects when used as a drug, which are reportedly stimulating rather than psychedelic.

5-IT acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA) with {{Abbrlink|EC₅₀|half-maximal effective concentration}} values of 12.9{{nbsp}}nM for dopamine, 13.3{{nbsp}}nM for norepinephrine, and 104.8{{nbsp}}nM for serotonin, and is also an MAO-A inhibitor, with an {{Abbrlink|IC₅₀|half-maximal inhibitory concentration}} of 200 to 1,600{{nbsp}}nM.{{cite journal | vauthors = Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH | title = The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue | journal = Neuropharmacology | volume = 101 | pages = 68–75 | date = February 2016 | pmid = 26362361 | pmc = 4681602 | doi = 10.1016/j.neuropharm.2015.09.004 }}{{cite journal | vauthors = Herraiz T, Brandt SD | title = 5-(2-Aminopropyl)indole (5-IT): a psychoactive substance used for recreational purposes is an inhibitor of human monoamine oxidase (MAO) | journal = Drug Testing and Analysis | volume = 6 | issue = 7–8 | pages = 607–613 | date = July–August 2014 | pmid = 24115740 | doi = 10.1002/dta.1530 | hdl = 10261/102667 }}{{cite journal | vauthors = Wagmann L, Brandt SD, Kavanagh PV, Maurer HH, Meyer MR | title = In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | journal = Toxicol Lett | volume = 272 | issue = | pages = 84–93 | date = April 2017 | pmid = 28302559 | doi = 10.1016/j.toxlet.2017.03.007 | url = }} Additional molecular target data have also been reported for 5-IT, including serotonin receptor interactions.{{cite journal | vauthors = Luethi D, Kolaczynska KE, Docci L, Krähenbühl S, Hoener MC, Liechti ME | title = Pharmacological profile of mephedrone analogs and related new psychoactive substances | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 4–12 | date = May 2018 | pmid = 28755886 | doi = 10.1016/j.neuropharm.2017.07.026 | url = }}

Alexander Shulgin wrote briefly about 5-IT in TiHKAL saying: "at 20 milligrams orally, [it] is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours."{{cite book |last1=Shulgin |first1=Alexander |authorlink1=Alexander Shulgin |title=Tihkal: A Continuation [Paperback] |publisher=Transform Press |date=December 1997 |url=https://www.erowid.org/library/books_online/tihkal/tihkal48.shtml |access-date=2012-02-08 |isbn=978-0-9630096-9-2}} 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.

The following symptoms can indicate 5-IT has been ingested: hyperthermia, tachycardia, increased blood pressure, dilated pupils (mydriasis), agitation, excessive sweating, jaw clenching, insomnia, disorientation, restlessness, anxiety, and tremor. It is a MAOI, and when combined with a contraindicated substance, it can lead to death.

5-IT has been attributed to 14 deaths of people in Sweden since its discovery.{{cite news | url=http://www.aftonbladet.se/nyheter/article15178324.ab | title=Nätdrog dödade 14 unga män | date=28 July 2012 | newspaper=Aftonbladet | language=Swedish}}{{cite journal | vauthors = Seetohul LN, Maskell PD, De Paoli G, Pounder DJ | title = Deaths associated with new designer drug 5-IT | journal = BMJ | volume = 345 | pages = e5625 | date = August 2012 | pmid = 22923530 | doi = 10.1136/bmj.e5625 | s2cid = 19956476 | url = http://eprints.hud.ac.uk/id/eprint/18545/1/Maskellbmj.e5625.full.pdf }} 5-IT was listed as the sole intoxicant in two cases but other drugs were also found in the twelve other post 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.{{cite web|title=Fem nya ämnen klassas som narkotika|url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/augusti/fem-nya-amnen-klassas-som-narkotika/ |publisher=The Swedish National Institute of Public Health |language=Swedish|access-date=10 September 2015}}

• 5-IT is a positional isomer of αMT, and as such is considered legally the same as αMT under the Controlled Substances Act in the US. (The Federal Analog Act includes a clause concerning the effects of the substance as well.)
• 5-IT was banned as a temporary class drug in June 2013, along with 9 other related compounds.{{cite web |url=https://www.gov.uk/government/publications/temporary-class-drug-order-report-on-benzofury-and-nbome-compounds |title=Temporary class drug order report on 5-6APB and NBOMe compounds |access-date=2013-07-11 |date=4 Jun 2013 |publisher=UK Home Office}} 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.{{cite web |url=http://www.legislation.gov.uk/ukdsi/2014/9780111110904 |title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 |access-date=2014-03-11 |author =UK Home Office |date=2014-03-05 |publisher=UK Government}}
• 5-IT is covered by the Australian analogue act as an analogue of MDA "by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures".{{cite web |url=http://www.comlaw.gov.au/ComLaw/Legislation/ActCompilation1.nsf/0/1B4A2DD73EF9A4BBCA2576040024B600/$file/CriminalCode1995_WD02.pdf |title=Criminal Code Act 1995 |access-date=2012-02-08 |date=2009-08-05 |publisher=Australian Government |quote=PAGE 503}}
• 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.
• 5-IT was made illegal in Denmark on 30 September 2012.
• 5-IT is an Anlage I controlled drug in Germany.
• 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.{{cite web |url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=COM:2013:0436:FIN:EN:PDF |title=COM(2013) 436 final |access-date=2013-06-26 |date=2013-06-25 |format=PDF |publisher=European Commission}}

• 6-API
• 5-APB
• 5-APBT
• 5-APDB
• αMT
• Amiflamine

{{Reflist}}

{{Stimulants}}

{{Monoamine releasing agents}}

{{Serotonin receptor modulators}}

{{Monoamine metabolism modulators}}

{{Phenethylamines}}

{{Chemical classes of psychoactive drugs}}

{{DEFAULTSORT:Aminopropyl)indole, 5-(2-}}

Category:5-HT2A agonists

Category:5-HT2B agonists

Category:Designer drugs

Category:Indoles

Category:Monoamine oxidase inhibitors

Category:Serotonin-norepinephrine-dopamine releasing agents

Category:Stimulants

Category:Substituted amphetamines