Lometraline

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Lometraline
Lometraline structure.png
Systematic (IUPAC) name
8-chloro-5-methoxy-N,N-dimethyl-1,2,3,4-tetrahydro-1-naphthalenamine
Clinical data
Legal status ?
Identifiers
CAS number 39951-65-0
34552-78-8 (hydrochloride)
ATC code None
PubChem CID 34789
ChemSpider 32014
Synonyms N,N-dimethyl-8-chloro-5-methoxy-1-aminotetralin
Chemical data
Formula C13H18ClNO 
Mol. mass 239.741 g/mol

Lometraline (INN; CP-14,368) is a drug which is an aminotetralin derivative.[1] A structural modification of the investigative neuroleptic pinoxepin, lometraline was originally patented by Pfizer as an antipsychotic, tranquilizer, and antiparkinsonian agent (likely as an anticholinergic).[2][3] However, it was instead later studied as a potential antidepressant and/or anxiolytic agent, but clinical studies revealed no psychoactivity at the doses used and further investigation was suspended.[1][4][5] However, further experimental modifications of the chemical structure of lometraline directly 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, which, remarkably, acts contrarily as a selective serotonin reuptake inhibitor (SSRI).[6]

See also[edit]

References[edit]

  1. ^ a b 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®)" (HTML). Retrieved 2012-04-27.