Tametraline
Tametraline.svg
Clinical data
ATC code
  • none
Identifiers
  • (1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H19N
Molar mass237.346 g·mol−1
3D model (JSmol)
  • CN[C@H](CC1)C(C=CC=C2)=C2[C@H]1C3=CC=CC=C3
  • InChI=1S/C17H19N/c1-18-17-12-11-14(13-7-3-2-4-8-13)15-9-5-6-10-16(15)17/h2-10,14,17-18H,11-12H2,1H3/t14-,17+/m0/s1 ☒N
  • Key:NVXPZMLRGBVYQV-WMLDXEAASA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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.

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.