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Compound

Tametraline

Original Wikipedia articleen.wikipedia.org/wiki/Tametraline revision used (24 October 2026)

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Overview

Tametraline (CP-24,441) is the parent of a series of chemical compounds investigated at Pfizer that eventually led to the development of sertraline.[1] WP

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. WP⚠ Wikipedia itself has flagged this text: citation needed.

1R-Methylamino-4S-phenyl-tetralin is a potent inhibitor of norepinephrine uptake in rat brain synaptosomes, reverses reserpine induced hypothermia in mice, and blocks uptake of ³H-Norepinephrine into rat heart.[2][3] WP

Tametraline is a norepinephrine–dopamine reuptake inhibitor.[4] WP

Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated. WP⚠ Wikipedia itself has flagged this text: citation needed.

Chemistry

Formula
C17H20ClN PC
Formula (Wikipedia infobox)
C17H19N WP⚠ Wikipedia and PubChem give different formulas. Both are shown as each source has it.
Molar mass (g/mol)
273.8 PC
IUPAC name (computed by PubChem)
(1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride PC
SMILES
CN[C@@H]1CC[C@H](C2=CC=CC=C12)C3=CC=CC=C3.Cl PC
InChIKey
XTSOELQVDLSJFM-SQQLFYIASA-N PC
PubChem CID
104180
IUPAC name
(1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine WP

Harm reduction information

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Sources

  1. Journal / agency Koe BK, Weissman A, Welch WM, Browne RG. 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. September 1983. doi:10.1016/S0022-3565(25)21773-6 · PMID 6310078
  2. Journal / agency Koe BK. Molecular geometry of inhibitors of the uptake of catecholamines and serotonin in synaptosomal preparations of rat brain. The Journal of Pharmacology and Experimental Therapeutics. December 1976. doi:10.1016/S0022-3565(25)30726-3 · PMID 994022
  3. Journal / agency Sarges R, Koe BK, Weissman A, Schaefer JP. 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. December 1974. doi:10.1016/S0022-3565(25)30003-0 · PMID 4427286
  4. Journal / agency Welch WM, Kraska AR, Sarges R, Koe BK. Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. Journal of Medicinal Chemistry. November 1984. doi:10.1021/jm00377a021 · PMID 6492080

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.