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
CompTox Dashboard (EPA)	DTXSID00865035
Chemical and physical data
Formula	C19H24N2
Molar mass	280.415 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 can be prepared by the reduction of amedalin with diborane. ^[2]

Daledalin synthesis

References

1. Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN   978-0-412-46630-4.
2. Cañas-Rodriguez A, Leeming PR (July 1972). "N-Phenyl-2-indolinones and N-phenylindolines. A new class of antidepressant agents". Journal of Medicinal Chemistry. 15 (7): 762–70. doi:10.1021/jm00277a017. PMID   5043876.
3. 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.
4. 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. PMID   994022.