5-IT

5-IT
Clinical data
Routes of
administration
Oral
ATC code none
Legal status
Legal status
Identifiers
CAS Number 3784-30-3 YesY
PubChem (CID) 55253543
ChemSpider 25991467 YesY
UNII W98BOE73HH
Chemical and physical data
Formula C11H14N2
Molar mass 174.24 g/mol
3D model (Jmol) Interactive image
  (verify)

5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571)[1] is an indole and phenethylamine derivative with empathogenic effects. Its preparation was first reported by Albert Hofmann in 1962.[2] It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.[3]

Chemistry

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.

Pharmacology

5-IT acts as a triple monoamine releasing agent with EC50 values of 12.9 nM for dopamine, 13.3 nM for norepinephrine and 104.8 nM for serotonin and also as MAO-A inhibitor.[4][5]

Dosage and effects

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."[6] 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.[3] It is an MAOI, and when combined with a contraindicated substance, it can lead to death.

Deaths

5-IT has been attributed to 14 deaths of people in Sweden since its discovery.[7][8] 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.[9]

Legality

See also

References

  1. Banks, M. L.; Bauer, C. T.; Blough, B. E.; Rothman, R. B.; Partilla, J. S.; Baumann, M. H.; Negus, S. S. (June 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): 274–284. doi:10.1037/a0036595. PMC 4067459Freely accessible. PMID 24796848.
  2. FR 1344579, Hofmann, Albert; Troxler, Franz, "Nouveaux derives de l'indole et leur preparation"
  3. 1 2 Katselou, Maria; Papoutsis, Ioannis; Nikolaou, Panagiota; Spiliopoulou, Chara; Athanaselis, Sotiris (January 2015). "5-(2-aminopropyl)indole: A new player in the drama of 'legal highs' alerts the community". Drug and Alcohol Review. 34 (1): 51–57. doi:10.1111/dar.12136. PMID 24634984.
  4. Julie A. Marusich; Kateland R. Antonazzo; Bruce E. Blough; Simon D. Brandt; Pierce V. Kavanagh; John S. Partilla; Michael H. Baumann (February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology. 101: 68–75. doi:10.1016/j.neuropharm.2015.09.004. PMID 26362361.
  5. Tomás Herraiz; Simon D. Brandt (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. PMID 24115740.
  6. Shulgin, Alexander (December 1997). Tihkal: A Continuation [Paperback]. Transform Press. ISBN 978-0-9630096-9-2. Retrieved 2012-02-08.
  7. "Nätdrog dödade 14 unga män". Aftonbladet (in Swedish). 28 July 2012.
  8. Seetohul, L. N.; Maskell, P. D.; De Paoli, G.; Pounder, D. J. (August 2012). "Deaths associated with new designer drug 5-IT". BMJ. 345: e5625. doi:10.1136/bmj.e5625. PMID 22923530.
  9. "Fem nya ämnen klassas som narkotika" (in Swedish). The Swedish National Institute of Public Health. Retrieved 10 September 2015.
  10. "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-11.
  11. UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
  12. "Criminal Code Act 1995" (PDF). Australian Government. 2009-08-05. Retrieved 2012-02-08. PAGE 503
  13. "COM(2013) 436 final" (PDF). European Commission. 2013-06-25. Retrieved 2013-06-26.

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