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Lometraline

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Chemical compound Pharmaceutical compound
Lometraline
Clinical data
Other namesN,N-dimethyl-8-chloro-5-methoxy-1-aminotetralin
ATC code
  • None
Identifiers
IUPAC name
  • 8-chloro-5-methoxy-N,N-dimethyl-1,2,3,4-tetrahydro-1-naphthalenamine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18ClNO
Molar mass239.74 g·mol
3D model (JSmol)
SMILES
  • Clc1ccc(OC)c2c1C(N(C)C)CCC2
InChI
  • InChI=1S/C13H18ClNO/c1-15(2)11-6-4-5-9-12(16-3)8-7-10(14)13(9)11/h7-8,11H,4-6H2,1-3H3
  • Key:MTWNWMGGMZUIMZ-UHFFFAOYSA-N

Lometraline (INN; developmental code name CP-14,368) is a drug and an aminotetralin derivative. A structural modification of tricyclic neuroleptics, lometraline was originally patented by Pfizer as an antipsychotic, tranquilizer, and antiparkinsonian agent. However, it was instead later studied as a potential antidepressant and/or anxiolytic agent, though clinical studies revealed no psychoactivity at the doses used and further investigation was suspended. Further experimental modifications of the chemical structure of lometraline resulted in the discovery of tametraline, a potent inhibitor of the reuptake of dopamine and norepinephrine, which in turn led to the discovery of the antidepressant sertraline, a selective serotonin reuptake inhibitor (SSRI).

References

  1. ^ Park S, Gershon S, Angrist B, Floyd A (February 1972). "Evaluation of an aminotetraline, CP 14.368, as an antidepressant". Current Therapeutic Research, Clinical and Experimental. 14 (2): 65–70. PMID 4401233.
  2. Drake E (27 January 1994). Saunders pharmaceutical word book, 1994. W.B. Saunders Co. ISBN 978-0-7216-5254-2. Retrieved 27 April 2012.
  3. United States. Patent Office (1972). "Lometraline: tranquillizer, anti-parkinson agent". Official gazette of the United States Patent Office: Patents. The Office. Retrieved 27 April 2012.
  4. McMahon FG (1974). Psychopharmacological agents. Futura Pub. Co. ISBN 978-0-87993-052-3. Retrieved 27 April 2012.
  5. Bayerische Julius-Maximilians-Universität Würzburg. Arbeitskreis für Schlafforschung (1973). The Nature of sleep. Die Natur des Schlafes. La nature du sommeil: International symposium, Würzburg, 23-26.9.1971. G. Fischer. ISBN 978-3-437-10295-0. Retrieved 27 April 2012.
  6. Koe BK, Harbert CA, Sarges R, Weissman A, Welch WM (2006). "Discovery of sertraline (Zoloft®)". Archived from the original on 2014-12-30. Retrieved 2012-04-27.
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