Lometraline

Lometraline
	File:Lometraline structure.png
Systematic (IUPAC) name
	8-chloro-5-methoxy-N,N-dimethyl-1,2,3,4-tetrahydro-1-naphthalenamine
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
Molecular mass	239.741 g/mol
	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; 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]

References