Benzindopyrine

Benzindopyrine
Clinical data
Other names	Pyrbenzindole; Purbenzindole; Benzylindolylethylpyridine; 4-(1-Benzyl-3-indolylethyl)pyridine
ATC code	None;
Identifiers
	IUPAC name 1-benzyl-3-(2-pyridin-4-ylethyl)indole;
CAS Number	16571-59-8;
PubChem CID	21770;
DrugBank	DB19669;
UNII	21Y024X5FO;
ChEMBL	ChEMBL2110797;
Chemical and physical data
Formula	C22H20N2
Molar mass	312.416 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)CN2C=C(C3=CC=CC=C32)CCC4=CC=NC=C4;
	InChI InChI=1S/C22H20N2/c1-2-6-19(7-3-1)16-24-17-20(21-8-4-5-9-22(21)24)11-10-18-12-14-23-15-13-18/h1-9,12-15,17H,10-11,16H2; Key:VRJCKJKZCZLXBK-UHFFFAOYSA-N;

Benzindopyrine (INNTooltip International Nonproprietary Name; developmental code name IN-461), also known as pyrbenzindole or as 4-(1-benzyl-3-indolylethyl)pyridine, is a drug described as a "psychotherapeutic agent", "tranquilizer", and "ataractic" which was never marketed.^[1]^[2]^[3]^[4]^[5] It is an indole derivative and an analogue of the neurotransmitter serotonin, though it is not a tryptamine.^[1]^[3]^[5] The drug was studied in the treatment of anxiety and depression, but was found to be no more effective than placebo.^[5] It is said to have central depressant effects in humans, though infrequently producing sleepiness and instead causing insomnia.^[6] Benzindopyrine was first described in the scientific literature by 1959.^[6]^[7]^[5]^[4] Methylindolylethylpyridine (IN-399; 4-(1-methyl-3-indolylethyl)pyridine), the analogue of benzindopyrine in which the 1-benzyl group has been replaced with a 1-methyl substitution, is also known.^[3]^[7]