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Indriline

Clinical data
Other names	Lu 3-083, MJ 1986.
Identifiers
CAS Number	7395-90-6
PubChem CID	23878
ChemSpider	22324
UNII	J2LLI1K6QQ
ChEMBL	ChEMBL2110854
CompTox Dashboard (EPA)	DTXSID90864052
Chemical and physical data
Formula	C19H21N
Molar mass	263.384 g·mol
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1(C=CC2=CC=CC=C21)C3=CC=CC=C3
InChI InChI=1S/C19H21N/c1-20(2)15-14-19(17-9-4-3-5-10-17)13-12-16-8-6-7-11-18(16)19/h3-13H,14-15H2,1-2H3 Key:KAQPNQMPHIRKJJ-UHFFFAOYSA-N

Indriline is a central nervous system stimulant with antidepressant activity and application in the treatment of gastric ulcers.

A patent using this chemical is assigned to Pharmacol.

Synthesis

The chemical synthesis of indriline has been described:

Treatment of 3-phenylindene (1) with n-butyl lithium and dimethylamino-2-choroethane gave indriline as well as some inactive isomer. Based on neighboring group participation (NGP), the reaction intermediate is presumably an aziridinium ion

According to Molbase the number of routes for preparing the starting 3-phenylindene is rich. For example from dihydrochalcone. A more classical synthesis is also described in a Pyrophendane patent.

References

1. US 3743746, Dungan K, Lish P, "Process of treating peptic ulcer with a non-anticholinergic agent", issued 1970, assigned to Mead Johnson & Co. 
2. Buchel L, Levy J (1968). "". Therapie (in French). 23 (5): 1135–46. PMID 4387506.
3. Dykstra SJ, Berdahl JM, Campbell KN, Combs CM, Lankin DG (May 1967). "Phenylindenes and phenylindans with antireserpine activity". Journal of Medicinal Chemistry. 10 (3): 418–428. doi:10.1021/jm00315a029. PMID 22185145.
4. ^ US 3360435, Alexander K, Merrill LP, issued 1967, assigned to Mead Johnson & Co. 
5. Saito S, Sato Y, Ohwada T, Shudo K (March 1994). "Friedel-Crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication". Journal of the American Chemical Society. 116 (6): 2312–2317. doi:10.1021/ja00085a010.

• Stimulants
• Indenes
• Dimethylamino compounds