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 =

| excretion =

| 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:Abandoned drugs

Category:Secondary amines

Category:Antidepressants

Category:Indolines

Category:Norepinephrine reuptake inhibitors

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