6-(2-Aminopropyl)indole

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6-(2-Aminopropyl)indole
6-API structure.tif
Systematic (IUPAC) name
2-(1H-indol-6-yl)-1-methyl-ethylamine
Clinical data
Oral
Identifiers
22196-72-1
PubChem CID 30999
ChemSpider 28759
Chemical data
Formula C11H14N2
174.24 g/mol

6-(2-Aminopropyl)indole (6-API, 6-IT) is an indole derivative with no history of use in humans. The analogue 5-API is known to be psychoactive, indicating 6-API may also be psychoactive by the same structure-activity relationship that links 5-APB and 6-APB.

Alexander Shulgin says in his book TiHKAL "From the normal 3-position to the 2, the 4, the 5, the 6 or the 7-positions. All five alpha-methyltryptamine isomers are known, but only one is known to be active in man as a CNS active material. This is the 5-isomer, 5-(2-aminopropyl)indole or 5-IT"[1].

Studies in dogs have also shown the drug to increase hemoglobin levels in the bloodstream.[1]

Legality[edit]

  • 6-API is a positional isomer of αMT, and as such is covered by the analogue act in the USA.
  • 6-API / 6-IT is illegal in the UK, as it was banned as a temporary class drug in June 2013, along with 9 other related compounds.[2]On March 5, 2014 the UK Home Office announced that 6-API would be made a class B drug on 10 June 2014 alongside every other benzofuran entactogen and many structurally related drugs.[3]
  • 6-API 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"[4]

See also[edit]

References[edit]

  1. ^ Maxwell, G. M. (1964). "The effects of an indole derivative 6-(2′-Aminopropyl indole) on the general and coronary haemodynamics of the intact dog". Cellular and Molecular Life Sciences 20 (9): 526–527. doi:10.1007/BF02154095. 
  2. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-11. 
  3. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11. 
  4. ^ "Criminal Code Act 1995" (PDF). Australian Government. 2009-08-05. Retrieved 2012-02-08. PAGE 503