Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline (CP-51,974-1).[1]
Sertraline has been called "3,4-dichloro-tametraline". This is correct but it is an oversimplification in the sense that sertraline is the S,S-isomer whereas tametraline is the 1R,4S-stereoisomer.
1R-Methylamino-4S-phenyl-tetralin is a potent inhibitor of norepinephrine uptake in rat brain synaptosomes,[2] reverses reserpine induced hypothermia in mice, and blocks uptake of 3H-Norepinephrine into rat heart.[3]
Tametraline is a norepinephrine-dopamine reuptake inhibitor.[4]
Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated.
^Koe BK, Weissman A, Welch WM, Browne RG (September 1983). "Sertraline, 1S,4S-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, a new uptake inhibitor with selectivity for serotonin". The Journal of Pharmacology and Experimental Therapeutics. 226 (3): 686–700. PMID 6310078.
^Koe BK (December 1976). "Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain". The Journal of Pharmacology and Experimental Therapeutics. 199 (3): 649–61. PMID 994022.
^Sarges R, Koe BK, Weissman A, Schaefer JP (December 1974). "Blockade of heart 3H-norepinephrine up-take by 4-phenyl-1-aminotetralines: implications for the active conformation of imipramine-like drugs". The Journal of Pharmacology and Experimental Therapeutics. 191 (3): 393–402. PMID 4427286.
^Welch WM, Kraska AR, Sarges R, Koe BK (November 1984). "Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins". Journal of Medicinal Chemistry. 27 (11): 1508–15. doi:10.1021/jm00377a021. PMID 6492080.
Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline (CP-51...
Stobbe condensation is also illustrated by the synthesis of the drug tametraline. Aldol condensation Polyketide synthase Dieckmann condensation Claisen...
on these compounds led to tametraline, a norepinephrine and weaker dopamine reuptake inhibitor. Development of tametraline was soon stopped because of...
of the chemical structure of lometraline resulted in the discovery of tametraline, a potent inhibitor of the reuptake of dopamine and norepinephrine, which...
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