6-(2-Aminopropyl)indole

6-(2-Aminopropyl)indole

Clinical data
Routes of administration	Oral
Legal status
Legal status	DE: Uncontrolled[1] Uncontrolled (but covered under the Federal Analogue Act in the United States and Australia and likely under similar bills in other countries^[clarification needed])^[citation needed]
Identifiers
IUPAC name 1-(1H-Indol-6-yl)propan-2-amine
CAS Number	22196-72-1
PubChem CID	30999
ChemSpider	28759
UNII	M7C77J017A
CompTox Dashboard (EPA)	DTXSID501030112
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol^−1
3D model (JSmol)	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^Y Key:QCFIFKAOUKPFPU-UHFFFAOYSA-N^Y

6-(2-Aminopropyl)indole (6-API, 6-IT) is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czechia in July 2016.^[2]

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.^[3]

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.^[4] 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.^[5]
• 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"^[6]
• 6-API is uncontrolled in Germany, as indole rings are not included as rings under the 2-phenethylamine derived section of the NPsG.^[1]

References

1. "New Psychoactive Substances Act (Neue-psychoaktive-Stoffe-Gesetz) (NpSG) Non-official translation" (PDF). Retrieved 9 November 2021.
2. Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA
3. Maxwell GM (September 1964). "The effects of an indole derivative 692'-amino-propyl indole) on the general and coronary haemodynamics of the intact dog". Experientia. 20 (9): 526–7. doi:10.1007/BF02154095. PMID 5856353. S2CID 7574163.
4. "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-07-11.
5. UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
6. "Criminal Code Act 1995" (PDF). Australian Government. 2009-08-05. Retrieved 2012-02-08. PAGE 503