6-(2-Aminopropyl)indole

6-(2-Aminopropyl)indole

Clinical data
Routes of administration	Oral
Legal status
Legal status	Uncontrolled (but covered under the Federal Analogue Act in the United States and Australia and likely under similar bills in other countries)
Identifiers
IUPAC name 1-(1H-Indol-6-yl)propan-2-amine
CAS Number	22196-72-1
PubChem (CID)	30999
ChemSpider	28759
Chemical and physical data
Formula	C11H14N2
Molar mass	174.24 g/mol
3D model (Jmol)	Interactive image
SMILES C1=C2C(=CC=C1CC(C)N([H])[H])C=C[N]2[H]
InChI InChI=1S/C11H14N2/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-5,7-8,13H,6,12H2,1H3 Key:QCFIFKAOUKPFPU-UHFFFAOYSA-N

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".

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

Legality

• 6-API is a positional isomer of αMT, and as such may be covered by the analogue act in the USA (depending on the nature of its psychoactive effect).
• 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]

References

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