Daledalin

Daledalin
Clinical data
ATC code	None;
Identifiers
	IUPAC name N-Methyl-3-(3-methyl-1-phenyl-2,3-dihydro-1H-indol-3-yl)propan-1-amine;
CAS Number	22136-27-2 ; 23226-37-1 (tosylate);
PubChem CID	31707;
ChemSpider	29403;
UNII	IT56261A5A;
ChEMBL	ChEMBL2110924;
Chemical and physical data
Formula	C19H24N2
Molar mass	280.409 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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.[1][2][3] It is a selective norepinephrine reuptake inhibitor, with no significant effects on the reuptake of serotonin and dopamine, and no antihistamine or anticholinergic properties.[2] [4]

Synthesis

Daledalin synthesis:[5]

David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 978-0-412-46630-4.
Canas-Rodriquez A, Leeming PR (1972). "N-Phenyl-2-indolinones and N-phenylindolines - New class of antidepressant agents". Journal of Medicinal Chemistry. 15 (7): 762–770. doi:10.1021/jm00277a017.
Edwards JG, Ollerenshaw DP (1974). "Daledalin tosylate: a controlled trial in depressive illness". Current Medical Research and Opinion. 2 (6): 305–12. doi:10.1185/03007997409114763. PMID 4614944.
Koe BK (December 1976). "Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain". Journal of Pharmacology and Experimental Therapeutics. 199 (3): 649–661.
Canas-Rodriguez, A. (1972). "N-Phenyl-2-indolinones and N-phenylindolines. New class of antidepressant agents". Journal of Medicinal Chemistry. 15 (7): 762–770. doi:10.1021/jm00277a017.

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