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Tametraline

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tametraline
Clinical data
Other namesCP-24,441
ATC code
  • none
Identifiers
  • (1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
PubChemCID
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 atPfizer that eventually led to the development ofsertraline.[1]

Sertraline has been called "3,4-dichloro-tametraline". This is correct but it is an oversimplification in the sense that sertraline is theS,S-isomer whereas tametraline is the 1R,4S-stereoisomer.[citation needed]

1R-Methylamino-4S-phenyl-tetralin is a potent inhibitor of norepinephrine uptake in rat brain synaptosomes,[2] reversesreserpine induced hypothermia in mice, and blocks uptake of3H-Norepinephrine into rat heart.[3]

Tametraline is anorepinephrine–dopamine reuptake inhibitor.[4]

Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated.[citation needed]

See also

[edit]

References

[edit]
  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.doi:10.1016/S0022-3565(25)21773-6.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.doi:10.1016/S0022-3565(25)30726-3.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.doi:10.1016/S0022-3565(25)30003-0.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.
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
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