4-Hydroxytryptamine

4-Hydroxytryptamine
Clinical data
Other names	4-HT; 4-HTA; N,N-Didesmethylpsilocin; Dinorpsilocin
Drug class	Serotonin receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist
Identifiers
	IUPAC name 3-(2-aminoethyl)-1H-indol-4-ol;
CAS Number	570-14-9;
PubChem CID	11297;
ChemSpider	10823;
UNII	DP0D1701D1;
KEGG	C21762;
ChEBI	CHEBI:139217;
ChEMBL	ChEMBL18855;
CompTox Dashboard (EPA)	DTXSID30205607 ;
Chemical and physical data
Formula	C10H12N2O
Molar mass	176.219 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC2=C(C(=C1)O)C(=CN2)CCN;
	InChI InChI=1S/C10H12N2O/c11-5-4-7-6-12-8-2-1-3-9(13)10(7)8/h1-3,6,12-13H,4-5,11H2; Key:FKIRTWDHOWAQGX-UHFFFAOYSA-N;

4-Hydroxytryptamine (4-HT, 4-HTA), also known as N,N-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active form of the tryptamine alkaloid norbaeocystin.

The compound is a serotonin receptor agonist, including of the serotonin 5-HT_2A receptor, but in contrast to certain closely related compounds like psilocin, appears to be non-hallucinogenic.

4-HT may occur naturally in Psilocybe baeocystis and Psilocybe cyanescens. It may serve as an alternative precursor in the biosynthesis of psilocybin (4-PO-DMT) in psilocybin mushrooms.