Tametraline

Tametraline

Clinical data
Other names	CP-24,441
ATC code	none
Identifiers
IUPAC name (1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number	52795-02-5  Y HCl:  52760-47-1  Y
PubChem CID	104180
ChemSpider	143316  N
UNII	440C8K5Y5K HCl:  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 N Key:NVXPZMLRGBVYQV-WMLDXEAASA-N N
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 1R,4S-stereoisomer.^{[ citation needed ]}

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.^{[ citation needed ]}

See also

• Cyproheptadine
• Dasotraline
• Desmethylsertraline
• EXP-561 (1-amino-4-phenylbicyclo[2.2.2]octane)
• JNJ-7925476
• Lometraline
• Nefopam
• Sertraline

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. 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.