Indriline

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−1
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: ^[1] Pharmacology. ^[2]

Synthesis

The chemical synthesis of indriline has been described: ^{[3] [4]}

Indriline synthesis

Treatment of 3-phenylindene [1961-97-3] (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 ^[4]

According to Molbase the number of routes for preparing the starting 3-phenylindene is rich. For example from dihydrochalcone. ^[5] 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). "[On the central and peripheral pharmacological properties of 1-(2 dimethylaminoethyl)-1-phenylidene]". 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.