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 Pharmacol.^[1]^[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

^ US 3743746, Dungan K, Lish P, "Process of treating peptic ulcer with a non-anticholinergic agent", issued 1970, assigned to Mead Johnson & Co.
^ 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.
^ 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.
^ ^a ^b US 3360435, Alexander K, Merrill LP, issued 1967, assigned to Mead Johnson & Co.
^ 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.

[1] US 3743746, Dungan K, Lish P, "Process of treating peptic ulcer with a non-anticholinergic agent", issued 1970, assigned to Mead Johnson & Co.

[pmid4387506-2] 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.

[US_3360435-4] 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.

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