5-(2-Aminopropyl)indole

5-(2-Aminopropyl)indole

Systematic (IUPAC) name
2-(1H-indol-5-yl)-1-methyl-ethylamine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled (but covered under the Federal Analogue Act in the United States and Australia and likely under similar bills in other countries)
Routes	Oral
Identifiers
CAS number	3784-30-3
ATC code	None
ChemSpider	25991467 Y
Chemical data
Formula	C11H14N2
Mol. mass	174.24 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:AULGMISRJWGTBA-UHFFFAOYSA-N Y
Y(what is this?)  (verify)

5-(2-Aminopropyl)indole (5-API, 5-IT) is an indole derivative.

Dosage and effects

Alexander Shulgin wrote briefly about 5-API 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." It did not have its own chapter in the book, unlike most other drugs he synthesised, perhaps indicating a lack of interesting qualities.

Legality

• 5-API is a positional isomer of αMT, and as such is covered by the analogue act in the USA.
• 5-API is legal in the UK, as it is a phenethylamine which is not substituted on the ring with "alkoxy, alkylenedioxy or halide substituents", nor explicitly named in the Misuse of Drugs Act
• 5-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"

See also

• alpha-Methyltryptamine
• 6-API
• Indanylaminopropane
• 6-APB
• 5-APB