Lometraline

Lometraline (INN; developmental code name CP-14,368) is a drug and an aminotetralin derivative.[1] A structural modification of tricyclic neuroleptics, lometraline was originally patented by Pfizer as an antipsychotic, tranquilizer, and antiparkinsonian agent.[2][3] 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.[1][4][5] 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 now widely popular antidepressant sertraline, a selective serotonin reuptake inhibitor (SSRI).[6]

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
Chemical and physical data
FormulaC13H18ClNO
Molar mass239.74 g·mol−1
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

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. Ellen Drake; W.B. Saunders Company (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). Official gazette of the United States Patent Office: Patents. The Office. Retrieved 27 April 2012.
  4. Francis Gilbert McMahon (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. B. Kenneth Koe, Charles A. Harbert, Reinhard Sarges, Albert Weissman, Willard M. Welch (2006). "Discovery of sertraline (Zoloft®)". Archived from the original on 2014-12-30. Retrieved 2012-04-27.{{cite web}}: CS1 maint: multiple names: authors list (link)
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