Tametraline

Tametraline

Clinical data
ATC code	none
Identifiers
IUPAC name (1R,4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number	52760-47-1 Y
PubChem CID	104180
ChemSpider	143316 N
UNII	440C8K5Y5K
Chemical and physical data
Formula	C17H19N
Molar mass	237.339 g/mol
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?)

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).

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, reverses reserpine induced hypothermia in mice, and blocks uptake of ³H into rat heart.

Tametraline is a norepinephrine-dopamine reuptake inhibitor.

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

Two routes have been previously described, one for aryl moieties containing electron withdrawing groups, and one for electron donating groups:

Sarges, R. . (1975). "Synthesis of phenyl-substituted 1-aminotetralines". The Journal of Organic Chemistry. 40 (9): 1216–1224. doi:10.1021/jo00897a008. 

"As expected, Friedel-Crafts cyclization of the diarylbutyric acid derivatives # to the most reactive ring was observed with little or none of the alternative isomer being detected."

"The KMnO₄ oxidation of the 1-aryl-tetralins # was observed to give 4-hydroxy-4-aryltetralones # instead of the expected tetralone # previously reported. As a result of this finding, direct oxidation of Grignard reaction product # was attempted and found to be a more efficient route."