6.7- dihydroxy-2-aminotetraline

HPLC, using a Crownpack CR column containing an 18-crown-6-type chiral crown ether, served to separate and resolve the enantiomers of 5,6-dihydroxy-2-aminotetraline (132a) and 6,7-dihydroxy-2-aminotetraline (132b) at pH 2.0 LOQ for enantiomeric impurities was <0.1%308. 

Extremely active compounds are found among 2-aminotetralines. 6,7-Dihydroxy-2-aminotetraline (4.85, ADTN) and its A-(n-propyl) derivative are well-studied 2-aminotetraline derivatives. Nomifensine (4.83) is related to these aminotetralines and is used as an antidepressant drug. The catechol analog of nomifensine (with two hydroxyls on the 4-phenyl ring) is also a potent inhibitor of NE and DA uptake. 

Dihydroxy-2- aminotetralin (ADTN) dimethyl ADTN acti ve inactive... 

Dihydroxy-2- aminotetralin primary amine acti ve i nacti ve... 

Some of the earliest and most complete efforts at structural dissection have been carried through by Cannon and his co-workers at the University of Iowa. These studies were initially directed toward elucidation of the pharmacophoric element within the structure of the emetic agent apomorphine, I. The suggestion by Pinder et al. (2) that the 5,6-dihydroxy-2-aminotetralin fragment was the active moiety was followed in short order by the report of Cannon et al. (3) that the N,N-dimethyl derivative ("M-7") II was a potent emetic in the dog. Additional pharmacology on M-7 provided by Long et al. (4) further illustrated the similarity between I and II. Both... 

Figure 16.3-13. Formation of 7,8-dihydroxy N-(di-n-propyl)-2-aminotetralin with Mucuna-phenoloxidase. Quinone formation is prevented in situ with ascorbate as reductant.

Phenoloxidase (monophenol monooxygenase, E.C. 1.14.18.1) introduces one atom of molecular oxygen into the substrate and was used in alginate-entrapped cells or in partially purified form. The pharmaceutical 7,8-dihydroxy-N-(di-n-propyl)-2-aminotetralin was produced continuously using a phenol oxidase suspension in dialysis tubing in an airlift fermenter coupled to an aluminium oxide column for selective product isolation (Figure 16.3-13)[6S1. A product concentration of 130 mg/L and a yield of 25 % were reached. 

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