Daledalin
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = N-Methyl-3-(3-methyl-1-phenyl-2,3-dihydro-1H-indol-3-yl)propan-1-amine
| image = Daledalin.svg
| tradename =
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| metabolism =
| elimination_half-life =
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| CAS_number = 22136-27-2
| CAS_supplemental =
{{CAS|23226-37-1}} (tosylate)
| ATC_prefix = None
| ATC_suffix =
| ChEMBL = 2110924
| PubChem = 31707
| ChemSpiderID = 29403
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IT56261A5A
| C=19 | H=24 | N=2
| smiles = c1cccc2c1C(C)(CN2c3ccccc3)CCCNC
}}
Daledalin (UK-3557-15) is an antidepressant which was synthesized and trialed for depression in the early 1970s, but was never marketed.{{cite book | first = David J. | last = Triggle | name-list-style = vanc | title = Dictionary of pharmacological agents | publisher = Chapman & Hall | location = London | year = 1997 | isbn = 978-0-412-46630-4 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=daledalin&pg=PA565}}{{cite journal | vauthors = Cañas-Rodriguez A, Leeming PR | title = N-Phenyl-2-indolinones and N-phenylindolines. A new class of antidepressant agents | journal = Journal of Medicinal Chemistry | volume = 15 | issue = 7 | pages = 762–70 | date = July 1972 | pmid = 5043876| doi = 10.1021/jm00277a017 }}{{cite journal | vauthors = Edwards JG, Ollerenshaw DP | title = Daledalin tosylate: a controlled trial in depressive illness | journal = Current Medical Research and Opinion | volume = 2 | issue = 6 | pages = 305–12 | year = 1974 | pmid = 4614944 | doi = 10.1185/03007997409114763 }} It is a selective norepinephrine reuptake inhibitor, with no significant effects on the reuptake of serotonin and dopamine, and no antihistamine or anticholinergic properties.{{cite journal | vauthors = Koe BK | author-link1 = Kenneth Koe | title = Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 199 | issue = 3 | pages = 649–661 |date=December 1976 | pmid = 994022| url = http://jpet.aspetjournals.org/content/199/3/649.abstract}}
Synthesis
Daledalin can be prepared by the reduction of amedalin with diborane.
:File:Daledalin synthesis.png{{clear-left}}
References
{{Reflist}}
{{Antidepressants}}
{{Monoamine reuptake inhibitors}}
Category:Norepinephrine reuptake inhibitors
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