# Indriline

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Indriline
> Markdown URL: https://mediated.wiki/source/Indriline.md
> Source: https://en.wikipedia.org/wiki/Indriline
> Source revision: 1330104765
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Stimulant and antidepressant drug}}
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{{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
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| PubChem = 23878
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| ChemSpiderID = 22324
| UNII = J2LLI1K6QQ
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| ChEMBL = 2110854
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| 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](/source/central_nervous_system_stimulant) with [antidepressant](/source/antidepressant) activity and application in the treatment of [gastric ulcer](/source/gastric_ulcer)s.

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](/source/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](/source/aziridinium) ion<ref name = "US 3360435" />

According to [Molbase](/source/Molbase) the number of routes for preparing the starting 3-phenylindene is rich. For example from [dihydrochalcone](/source/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](/source/Pyrophendane) patent.

== References ==
{{Reflist}}

{{Antidepressants}}
{{Monoamine reuptake inhibitors}}
{{Stimulants}}

Category:Stimulants
Category:Indenes
Category:Dimethylamino compounds

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Adapted from the Wikipedia article [Indriline](https://en.wikipedia.org/wiki/Indriline) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Indriline?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.