5-IT

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(Redirected from
5-(2-Aminopropyl)indole
)
5-IT
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1H-Indol-5-yl)propan-2-amine
JSmol)
  • CC(N)Cc2cc1cc[nH]c1cc2
  • InChI=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 checkY
  • Key:AULGMISRJWGTBA-UHFFFAOYSA-N checkY
  (verify)

5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571)

recreational drug by online vendors since 2011.[3]

Chemistry

Although 5-IT is a

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:

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.

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

  • 5-IT is a positional isomer of
    Controlled Substance 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.[10] 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.[11]
  • 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".[12]
  • 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.[13]

See also

References

  1. PMID 24796848
    .
  2. ^ FR 1344579, Hofmann, Albert; Troxler, Franz, "Nouveaux derives de l'indole et leur preparation" 
  3. ^
    PMID 24634984
    .
  4. PMID 26362361
    .
  5. PMID 24115740
    .
  6. ISBN 978-0-9630096-9-2
    . Retrieved 2012-02-08.
  7. ^ "Nätdrog dödade 14 unga män". Aftonbladet (in Swedish). 28 July 2012.
  8. S2CID 19956476
    .
  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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