Tametraline (original) (raw)
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Chemical compound
Pharmaceutical compound
Tametraline
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|---|---|
| Clinical data | |
| Other names | CP-24,441 |
| ATC code | none |
| Identifiers | |
| IUPAC name (1_R_,4_S_)-_N_-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine | |
| CAS Number | 52795-02-5  YHCl: 52760-47-1 Y |
| PubChem CID | 104180 |
| ChemSpider | 143316  N |
| UNII | 440C8K5Y5KHCl: 2FY1A2A305 Y |
| CompTox Dashboard (EPA) | DTXSID90200774  |
| Chemical and physical data | |
| Formula | C17H19N |
| Molar mass | 237.346 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES CN[C@H](CC1)C(C=CC=C2)=C2[C@H]1C3=CC=CC=C3 | |
| InChI 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 NKey:NVXPZMLRGBVYQV-WMLDXEAASA-N N |
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| NY (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.[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 1_R,4_S_-stereoisomer.[_citation needed_]
1_R_-Methylamino-4_S_-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.[_citation needed_]
- Cyproheptadine
- Dasotraline
- Desmethylsertraline
- EXP-561 (1-amino-4-phenylbicyclo[2.2.2]octane)
- JNJ-7925476
- Lometraline
- Nefopam
- Sertraline
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.