Lometraline

Lometraline
Clinical data
Other names	N,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	39951-65-0 ; 34552-78-8 (hydrochloride);
PubChem CID	34789;
ChemSpider	32014;
UNII	V78B234QEY;
KEGG	D02669;
ChEMBL	ChEMBL2111119;
CompTox Dashboard (EPA)	DTXSID70865981 ;
Chemical and physical data
Formula	C13H18ClNO
Molar mass	239.74 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[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]

References

^ ^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.
^ 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.
^ United States. Patent Office (1972). Official gazette of the United States Patent Office: Patents. The Office. Retrieved 27 April 2012.
^ Francis Gilbert McMahon (1974). Psychopharmacological agents. Futura Pub. Co. ISBN 978-0-87993-052-3. Retrieved 27 April 2012.
^ 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.
^ 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)