|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||237.339 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
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-Norepinephrine into rat heart.
Indatraline is an indanamine homolog of tetralin-based tametraline, although in the case of indatraline the product is pm-dichlorinated.
"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."
In the case of 3,4-dichloro product, approximately 50:50 cis-/trans- ratio was achieved, according to the reference.
CAN radical induced dimerization of styrene
Certain aromatic substitutients have a potentiating effect (e.g., p-Br), whereas others negate the compound's intrinsic activity.
It is not right to think of the dimethyl analogs as a "prodrug" to the monomethylated drugs (cf. indatraline, "31,345"), but it is correct that it is a "latentiated" form of the drug. This word is from the salsalate page. This was the reason why sertraline was made only as monomethylated because apparently according to the orders the 1° amine is inactive therefore the drug would have a shorter duration of activity.
Enantiopurified trans- and cis-aminotetraline derivatives
|Enantiopurified 4-aryl-aminotetralins IC50 (μM)|
(±)-Sertraline is not entirely SERT selective until it has been resolved into the S,S-enantiomer.
In terms of the trans- isomers there is relatively marked separation in the activity between the R,S- and S,R-enantiomers. This stands in contrast to what has been observed in the homologous indamine class where both of the trans- enantiomers possessed significant TRI activity at all three of the monoamine transporters.
Racemic cis- and trans-aminotetraline derivatives
The primary amines are claimed to completely lack any affinity for the transporters.
- Cyproheptadine [4-(5H-dibenz-[a,d]cyclohepten-5-ylidine)-1-methylpiperidine]
- EXP-561 (1-amino-4-phenylbicyclo[2.2.2]octane)
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- US patent 4045488, Sarges, Reinhard, "Aminophenyltetralin compounds", issued 1977-08-30, assigned to Pfizer Inc.
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- "A CAN-induced cyclodimerization–Ritter trapping strategy for the one-pot synthesis of 1-amino-4-aryltetralins from styrenes: Vijay Nair, Roshini Rajan and Nigam P. Rath". Abstract. Organic Chemistry Portal. Reto Müller. n.d. Retrieved November 10, 2019.
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