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Daledalin

From Wikipedia, the free encyclopedia
Daledalin
Clinical data
ATC code
  • None
Identifiers
  • N-Methyl-3-(3-methyl-1-phenyl-2,3-dihydro-1H-indol-3-yl)propan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H24N2
Molar mass280.415 g·mol−1
3D model (JSmol)
  • 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

[edit]

Daledalin can be prepared by the reduction of amedalin with diborane.[2]

Daledalin synthesis

References

[edit]
  1. Triggle DJ (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 978-0-412-46630-4.
  2. 1 2 3 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.