5-API

5-IT
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	AU: Illegal CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I (positional isomer) Likely illegal in other countries
Identifiers
IUPAC name 1-(1H-Indol-5-yl)propan-2-amine
CAS Number	3784-30-3^Y
PubChem CID	55253543
ChemSpider	25991467^Y
UNII	W98BOE73HH
ECHA InfoCard	100.236.959
Chemical and physical data
Formula	C₁₁H₁₄N₂
Molar mass	174.24 g/mol
3D model (Jmol)	Interactive image
SMILES CC(N)Cc2cc1ccnc1cc2
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

5-(2-Aminopropyl)indole (5-API, 5-IT, PAL-571) is an indole and phenethylamine derivative with empathogenic 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.

Although 5-IT is a positional isomer of the tryptamine drug αMT, the compound is not itself a tryptamine as the indole ring is substituted at the 5 position rather than at the 3 position. The compound is closer chemically to phenethylamine derivatives such as 5-APB. This is reflected in the compound's effects when used as a drug, which are reportedly stimulating rather than psychedelic.

5-IT acts as a triple monoamine releasing agent with EC₅₀ values of 12.9 nM for dopamine, 13.3 nM for norepinephrine and 104.8 nM for serotonin and also as MAO-A inhibitor.

Alexander Shulgin wrote briefly about 5-IT 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." As 5-IT is not a tryptamine and thus not within the scope of the book, it is not discussed in any more detail than this.

The following symptoms can indicate 5-IT has been ingested: hyperthermia, tachycardia, increased blood pressure, dilated pupils (mydriasis), agitation, excessive sweating, jaw clenching, insomnia, disorientation, restlessness, anxiety, and tremor. It is an MAOI, and when combined with a contraindicated substance, it can lead to death.

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Wikipedia