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Daledalin

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Chemical compound
Pharmaceutical compound
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
Formula C19H24N2
Molar mass 280.415 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. ^ a b c 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.
SSRIs Tooltip Selective serotonin reuptake inhibitors
SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors
NRIs Tooltip Norepinephrine reuptake inhibitors
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants
SARIs Tooltip Serotonin antagonist and reuptake inhibitors
SMS Tooltip Serotonin modulator and stimulators
Others
TCAs Tooltip Tricyclic antidepressants
TeCAs Tooltip Tetracyclic antidepressants
Others
Non-selective
MAOA Tooltip Monoamine oxidase A-selective
MAOB Tooltip Monoamine oxidase B-selective
Miscellaneous
DAT Tooltip Dopamine transporter
(DRIs Tooltip Dopamine reuptake inhibitors)
NET Tooltip Norepinephrine transporter
(NRIs Tooltip Norepinephrine reuptake inhibitors)
SERT Tooltip Serotonin transporter
(SRIs Tooltip Serotonin reuptake inhibitors)
VMATs Tooltip Vesicular monoamine transporters
Others
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