5-(2-Aminopropyl)indole

5-(2-Aminopropyl)indole
Clinical data
Other names	5-API; 5-IT; PAL-571; PAL571; Indolylaminopropane; 3,4-Pyrrolo[b]amphetamine
Routes of; administration	Oral
Drug class	Serotonin–norepinephrine–dopamine releasing agent; Serotonin receptor modulator; Monoamine oxidase inhibitor; Stimulant
ATC code	None;
Legal status
Legal status	AU: Illegal; CA: Schedule I; DE: Anlage I (Authorized scientific use only); UK: Class B; US: Schedule I (positional isomer); Likely illegal in other countries;
Pharmacokinetic data
Duration of action	12 hours
Identifiers
	IUPAC name 1-(1H-indol-5-yl)propan-2-amine;
CAS Number	3784-30-3 ;
PubChem CID	55253543;
ChemSpider	25991467 ;
UNII	W98BOE73HH;
CompTox Dashboard (EPA)	DTXSID30873562 ;
ECHA InfoCard	100.236.959
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(N)Cc2cc1cc[nH]c1cc2;
	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 ; Key:AULGMISRJWGTBA-UHFFFAOYSA-N ;
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5-(2-Aminopropyl)indole (5-API or 5-IT), also known as 3,4-pyrrolo[b]amphetamine or by the code name PAL-571, is an indole and amphetamine derivative with stimulant effects. Its preparation was first reported by Albert Hofmann in 1962. It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.