5-(2-Aminopropyl)indole

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5-(2-Aminopropyl)indole
5-IT structure.png
Systematic (IUPAC) name
2-(1H-indol-5-yl)-1-methyl-ethylamine
Clinical data
Legal status Uncontrolled (but covered under the Federal Analogue Act in the United States and Australia and likely under similar bills in other countries)
Routes Oral
Identifiers
CAS number 3784-30-3 YesY
ATC code None
ChemSpider 25991467 YesY
Chemical data
Formula C11H14N2 
Mol. mass 174.24 g/mol
 YesY (what is this?)  (verify)

5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571)[1] is an indole derivative with stimulant effects. Its preparation was first reported by Albert Hofmann in 1962.[2] It is a designer drug that has been openly sold as a research chemical by online vendors since 2011.[citation needed]

Chemistry[edit]

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.

Dosage and effects[edit]

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."[3] 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: dilated pupils, sweat, motoric unrest, high pulse, high blood pressure, high body temperature.[citation needed] In severe cases these symptoms can lead to death.[4]

Deaths[edit]

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 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 20-30. Eleven non-fatal poisonings due to 5-IT also reportedly occurred during the same time period.[4]

Legality[edit]

  • 5-IT is a positional isomer of αMT, and as such is considered legally the same as αMT under the Controlled Substance Act in the USA. (The Federal Analog Act includes a clause concerning the effects of the substance as well.)
  • 5-IT is illegal in the UK, as it was banned as a temporary class drug in June 2013, along with 9 other related compounds.[7]
  • 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".[8]
  • 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.
  • 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.[9]

See also[edit]

References[edit]

  1. ^ Banks, M. L.; Bauer, C. T.; Blough, B. E.; Rothman, R. B.; Partilla, J. S.; Baumann, M. H.; Negus, S. S. (2014). "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Experimental and Clinical Psychopharmacology 22 (3): 274. doi:10.1037/a0036595. PMID 24796848.  edit
  2. ^ FR 1344579, Hofmann, Albert; Troxler, Franz, "Nouveaux derives de l'indole et leur preparation" 
  3. ^ Shulgin, Alexander (December 1997). Tihkal: A Continuation [Paperback]. Transform Press. ISBN 978-0-9630096-9-2. Retrieved 2012-02-08. 
  4. ^ a b "Folkhälsoinstitutet föreslår förbud för ny livsfarlig nätdrog". The Swedish National Institute of Public Health. Retrieved 28 July 2012. 
  5. ^ "Nätdrog dödade 14 unga män". Aftonbladet. 2012-07-28. Retrieved 2012-07-28. 
  6. ^ Seetohul, L. N.; Maskell, P. D.; De Paoli, G.; Pounder, D. J. (2012). "Deaths associated with new designer drug 5-IT". BMJ 345: e5625. doi:10.1136/bmj.e5625. PMID 22923530.  edit
  7. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-11. 
  8. ^ "Criminal Code Act 1995" (PDF). Australian Government. 2009-08-05. Retrieved 2012-02-08. "PAGE 503" 
  9. ^ "COM(2013) 436 final" (PDF). European Commission. 2013-06-25. Retrieved 2013-06-26.