{{Short description|Stimulant and antidepressant drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = Indriline | image = Indriline.svg | image_class = skin-invert-image | width = 250px | caption =
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<!-- Identifiers --> | CAS_number = 7395-90-6 | CAS_supplemental = | PubChem = 23878 | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 22324 | UNII = J2LLI1K6QQ | KEGG = | ChEBI = | ChEMBL = 2110854 | NIAID_ChemDB = | PDB_ligand = | synonyms = Lu 3-083, MJ 1986.
<!--Chemical data--> | 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:<ref>{{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 }}</ref> Pharmacology.<ref name="pmid4387506">{{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 = }}</ref> ==Synthesis== The chemical synthesis of indriline has been described:<ref>{{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 }}</ref><ref name = "US 3360435">{{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. }}</ref> center|400px|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<ref name = "US 3360435" />
According to Molbase the number of routes for preparing the starting 3-phenylindene is rich. For example from dihydrochalcone.<ref>{{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 }}</ref> A more classical synthesis is also described in a Pyrophendane patent.
== References == {{Reflist}}
{{Antidepressants}} {{Monoamine reuptake inhibitors}} {{Stimulants}}
Category:Stimulants Category:Indenes Category:Dimethylamino compounds