(S)-5,6-Dimethoxy-1,2,3,4-tetrahydro-2-naphthalenamine– L-(+)-Mandelic Acid (1/1): the Absolute Configuration of a Precursor of the Active Stereoisomer of 5,6-ADTN, an Important Dopaminergic Agonist

Abstract

The structure determination of the title compound, CI2HlsNO~.CsHTO3-, has allowed the absolute configuration of the cation to be established. The demethylated base, (S)-5,6-dihydroxy-1,2,3,4-tetrahydro-2-naphthalena-mine, or (2S)-5,6-ADTN, is responsible for the dopaminergic activity; this work shows that it has the same spatial arrangement as (6aR)-apomorphine.

An Alternative Synthesis of the Dopaminergic Drug 2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐5,6‐diol (5,6‐ADTN)

“…thoxy-1,2,3,4-tetrahydronaphthalene-L-mandelic acid, a precursor of (S)-4, was described by Fantucci et al [12].…”