indriline
{{Short description|Stimulant and antidepressant drug}}
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{{Infobox drug
| drug_name = Indriline
| image = Indriline.svg
| width = 250px
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| CAS_number = 7395-90-6
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| PubChem = 23878
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| DrugBank =
| ChemSpiderID = 22324
| UNII = J2LLI1K6QQ
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| ChEMBL = 2110854
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| synonyms = Lu 3-083, MJ 1986.
| C=19 | H=21 | N=1
| StdInChI=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
| StdInChIKey = KAQPNQMPHIRKJJ-UHFFFAOYSA-N
| SMILES = CN(C)CCC1(C=CC2=CC=CC=C21)C3=CC=CC=C3
}}
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.{{cite patent | title = Process of treating peptic ulcer with a non-anticholinergic agent | inventor = Dungan K, Lish P | country = US | number = 3743746 | gdate = 1970 | assign = Mead Johnson & Co. | url = https://patents.google.com/patent/US3743746A/en?oq=US+3743746 }}{{cite journal | vauthors = Buchel L, Levy J | title = [On the central and peripheral pharmacological properties of 1-(2 dimethylaminoethyl)-1-phenylidene] | language = French | journal = Therapie | volume = 23 | issue = 5 | pages = 1135–46 | date = 1968 | pmid = 4387506 | doi = | url = }}
Synthesis
The chemical synthesis of indriline has been described:{{cite journal | vauthors = Dykstra SJ, Berdahl JM, Campbell KN, Combs CM, Lankin DG | title = Phenylindenes and phenylindans with antireserpine activity | journal = Journal of Medicinal Chemistry | volume = 10 | issue = 3 | pages = 418–428 | date = May 1967 | pmid = 22185145 | doi = 10.1021/jm00315a029 }}{{cite patent | country = US | number = 3360435 | inventor = Alexander K, Merrill LP | url = https://patents.google.com/patent/US3360435A/en?oq=US+3360435 | gdate = 1967 | assign = Mead Johnson & Co. }}
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
According to Molbase the number of routes for preparing the starting 3-phenylindene is rich. For example from dihydrochalcone.{{cite journal | vauthors = Saito S, Sato Y, Ohwada T, Shudo K | title = Friedel-Crafts-type cyclodehydration of 1,3-diphenyl-1-propanones. Kinetic evidence for the involvement of dication. | journal = Journal of the American Chemical Society | date = March 1994 | volume = 116 | issue = 6 | pages = 2312-2317 | doi = 10.1021/ja00085a010 }}
A more classical synthesis is also described in a Pyrophendane patent.
References
{{Reflist}}
{{Antidepressants}}
{{Monoamine reuptake inhibitors}}
{{Stimulants}}