85379-09-5

Usage

Biological Activity

Dopamine receptor antagonist with preferential action at presynaptic receptors (pK i values are 6.95, 6.67, 6.37, 6.21 and 6.07 at hD 3 . hD 4 , hD 2S , hD 2L and rD 2 receptors respectively).

InChI:InChI=1/C15H23NO/c1-4-10-16-14-9-8-13-12(11(14)2)6-5-7-15(13)17-3/h5-7,11,14,16H,4,8-10H2,1-3H3/t11-,14+/m0/s1

Upstream product

• 90295-53-7 cis-5-methoxy-1-methyl-2-(n-propylamino)tetralin 
• 90295-48-0 trans-2-amino-5-methoxy-1-methyltetralin 
• 90295-58-2 5-methoxy-1-methyl-2-tetralone oxime 
• 90295-47-9 1,2-dihydro-4-methyl-8-methoxynaphthalene 
• 33892-75-0 5-Methoxy-1-tetralone 
• 42263-75-2 1-methyl-5-methoxy-2-tetralone 
• 90295-50-4 N-((1S,2S)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-propionamide 
• 250598-37-9 Toluene-4-sulfonic acid (1S,2S)-5-methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl ester 
• 250598-36-8 cis-1-methyl-2-azido-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 250598-35-7 trans-5-methoxy-1-methyl-1,2,3,4-tetrahydro-2-naphthol 
• 102607-13-6 (1S,2R)-2-amino-5-methoxy-1-methyltetralin 
• 865070-96-8 5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 106499-54-1 N-((1S,2R)-5-Methoxy-1-methyl-1,2,3,4-tetrahydro-naphthalen-2-yl)-propionamide 

Downstream Products

• 95999-12-5 (+)-UH 232 

Relevant academic research and scientific papers

A short and efficient asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1- methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232)

A general practical asymmetric synthesis of (1S,2R)-(+)-5-methoxy-1- methyl-2-(di-n-propylamino)tetralin hydrochloride (UH-232) was developed in a short and efficient method in high optical purity starting from commercially available 5-methoxy-1-tetralone. Asymmetric hydroboration of 5-methoxy-1- methyl-3,4-dihydronaphthalene with monoisopinocampheylborane followed by treatment with NaOH/H2O2 afforded key intermediate tetrahydronaphthol 4. Compound 4 was converted to the target molecule 1 using straightforward reactions.

Resolved cis- and trans-2-amino-5-methoxy-1-methyltetralins: Central dopamine receptor agonists and antagonists

A series of 35 stereochemically well-defined C1-methyl-substituted derivatives of the potent dopamine (DA) receptor agonist 5-hydroxy-2-(di-n-propylamino)tetralin (5-OH-DPAT) have been synthesized. The compounds were tested for central DA receptor agonistic and antagonistic activity, by use of biochemical and behavioral tests in rats. In addition, the compounds were tested for in vivo interactions with 5,6-dihydroxy-2-(di-n-propylamino)tetralin (DiPr-5,6-ADTN). On the basis of pharmacological activity profiles, the active compounds have been classified into four groups: (a) classical pre- and postsynaptic DA receptor agonists, (b) DA receptor agonists with preferential action at presynaptic receptors, (c) pre- and postsynaptic DA receptor antagonists, and (d) DA receptor antagonists with preferential action at presynaptic receptors. Results obtained indicate that both 2R and 2S enantiomers of C5-oxygenated 2-aminotetralins may be able to bind to DA receptors but that only 2S antipodes are able to activate the receptors. O-Methylation of the C5-oxygenated (1S,2R)-2-amino-1-methyltetralin derivatives tends to increase their DA receptor antagonistic activity, whereas decrease of the size of the N-substituent(s) from n-propyl to ethyl or methyl appears to increase their activity at postsynaptic DA receptors.

C1-Methylated 5-hydroxy-2-(dipropylamino)tetralins: central dopamine-receptor stimulating activity.

C1-Methylated derivatives of the potent dopaminergic agonist 5-hydroxy-2-(di-n-propylamino)tetralin (6) have been synthesized and tested for central dopamine (DA) receptor stimulating activity, by using biochemical and behavioral tests in rats. Both cis- and trans-5-hydroxy-1-methyl-2-(di-n-propylamino) tetralin (4 and 3) may be classified as central DA-receptor agonists, albeit of lower potency than 6. The results obtained indicate that both 4 and 3 display DA-autoreceptor stimulation capacity. However, only one of the isomers, trans-3, is able to elicit clear-cut postsynaptic DA receptor agonist actions at larger doses. 5-Hydroxy-1,1-dimethyl-2-(n-propylamino) tetralin (5) was found to be inactive.