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]

References

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. Retrieved 11 May 2026.
^ Negwer M (1 August 2022). Martin Negwer: Organic-chemical drugs and their synonyms. Volume 2. Walter de Gruyter GmbH & Co KG. ISBN 978-3-11-261134-0. Retrieved 11 May 2026.
^ ^a ^b ^c Usdin E, Effron DH (1972). Psychotropic Drugs and Related Compounds. National Institute of Mental Health. Retrieved 12 May 2026.
^ ^a ^b Latiolais CJ, Eckel FM (1 March 1963). "Investigational Drugs". American Journal of Health-System Pharmacy. 20 (3): 145–151. doi:10.1093/ajhp/20.3.145. ISSN 1079-2082.
^ ^a ^b ^c ^d Hankoff LD, Rudorfer L, Paley HM (1962). "The psychiatric use of pyrbenzindole: a double blind outpatient study". The Journal of New Drugs. 2 (3): 167–172. doi:10.1177/009127006200200304. PMID 13904353.
^ ^a ^b Bodi T, Levy H, Share I, Slap JW, Nodine JH, Moyer JH (September 1959). "Clinical trial of a new indole derivative in patients with psychoneurosis". Antibiotic Medicine & Clinical Therapy. 6: 521–525. PMID 13801927.
^ ^a ^b Bodi T, Nodine JH, Levy HA, Siegler PE, Moyer JH (May 1960). "Preliminary study of the therapeutic and toxic effects of 4-(1-methyl-3-indolylethyl)pyridine hydrochloride in ambulatory patients with psychoneurosis". Toxicology and Applied Pharmacology. 2 (3): 254–263. doi:10.1016/0041-008x(60)90055-7. PMID 13801929.

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