5-IT explained

Verifiedrevid:451227220
Iupac Name:1-(1H-Indol-5-yl)propan-2-amine
Legal Us:Schedule I
Legal Au Comment:Illegal
Legal Us Comment:(positional isomer)
Legal Status:Likely illegal in other countries
Legal Ca:Schedule I
Legal Uk:Class B
Legal De:Anlage I
Routes Of Administration:Oral
Cas Number:3784-30-3
Atc Prefix:none
Pubchem:55253543
Chemspiderid:25991467
Unii:W98BOE73HH
C:11
H:14
N:2
Smiles:CC(N)Cc2cc1cc[nH]c1cc2
Stdinchi:1S/C11H14N2/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-5,7-8,13H,6,12H2,1H3
Stdinchikey:AULGMISRJWGTBA-UHFFFAOYSA-N

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 a 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 and 30. Eleven non-fatal poisonings due to 5-IT also reportedly occurred during the same time period.[9]

Legality

See also

Notes and References

  1. Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS . 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 . June 2014 . 24796848 . 4067459 . 10.1037/a0036595 .
  2. FR . 1344579 . Nouveaux derives de l'indole et leur preparation . Hofmann, Albert
    Troxler, Franz
    . November 21, 1962.
  3. Katselou M, Papoutsis I, Nikolaou P, Spiliopoulou C, Athanaselis S . 5-(2-aminopropyl)indole: a new player in the drama of 'legal highs' alerts the community . Drug and Alcohol Review . 34 . 1 . 51–7 . January 2015 . 24634984 . 10.1111/dar.12136 . free .
  4. Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH . 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 . February 2016 . 26362361 . 4681602 . 10.1016/j.neuropharm.2015.09.004 .
  5. Herraiz T, Brandt SD . 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 . 607–13 . July–August 2014 . 24115740 . 10.1002/dta.1530 . 10261/102667 .
  6. Book: Shulgin . Alexander . Alexander Shulgin . Tihkal: A Continuation [Paperback] ]. Transform Press . December 1997 . 2012-02-08 . 978-0-9630096-9-2.
  7. News: Nätdrog dödade 14 unga män . 28 July 2012 . Aftonbladet . Swedish.
  8. Seetohul LN, Maskell PD, De Paoli G, Pounder DJ . Deaths associated with new designer drug 5-IT . BMJ . 345 . e5625 . August 2012 . 22923530 . 10.1136/bmj.e5625 . 19956476 .
  9. Web site: Fem nya ämnen klassas som narkotika. The Swedish National Institute of Public Health . Swedish. 10 September 2015.
  10. Web site: Temporary class drug order report on 5-6APB and NBOMe compounds . 2013-07-11 . 4 Jun 2013 . UK Home Office.
  11. Web site: The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 . 2014-03-11 . UK Home Office . 2014-03-05 . UK Government.
  12. Web site: Criminal Code Act 1995 . 2012-02-08 . 2009-08-05 . Australian Government . PAGE 503.
  13. Web site: COM(2013) 436 final . 2013-06-26 . 2013-06-25 . PDF . European Commission.

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