Tametraline

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]

Other namesCP-24,441

ATC code

• none

CAS Number

• 52795-02-5 ^Y
• HCl: 52760-47-1 ^Y

PubChem CID

• 104180

Quick facts Clinical data, Other names ...

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)

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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]}