| Drug Name: | (R)-1-Aminoindan |
| Width: | 125px |
| Cas Number: | 10277-74-4 |
| Pubchem: | 2733933 |
| Chemspiderid: | 2015696 |
| Unii: | I17RC77CJ2 |
| Chembl: | 4573666 |
| Synonyms: | (R)-1-Aminoindane; (R)-(–)-1-Aminoindan; (R)-AI; (R)-1-AI; TVP-136; TV-136; (R)-(−)-1-Indanamine |
| Iupac Name: | (1R)-2,3-dihydro-1H-inden-1-amine |
| C: | 9 |
| H: | 11 |
| N: | 1 |
| Smiles: | C1CC2=CC=CC=C2[C@@H]1N |
| Stdinchi: | 1S/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2/t9-/m1/s1 |
| Stdinchikey: | XJEVHMGJSYVQBQ-SECBINFHSA-N |
(R)-1-Aminoindan ((R)-1-AI; developmental code name TVP-136 or TV-136), or (R)-1-aminoindane, is the major metabolite of the selective MAO-B inhibitor and antiparkinsonian agent rasagiline ((R)-N-propargyl-1-aminoindan). In contrast to rasagiline, it lacks significant monoamine oxidase inhibition. In addition, unlike selegiline and its amphetamine metabolites, it lacks monoamine reuptake-inhibiting and -releasing activities and associated amphetamine-like psychostimulant effects. However, (R)-1-aminoindan retains neuroprotective effects and certain other activities.
In contrast to rasagiline, (R)-1-aminoindan is either devoid of monoamine oxidase inhibition or shows only weak inhibition of MAO-B.[1] [2] Unlike selegiline and its levomethamphetamine and levoamphetamine metabolites, rasagiline and (R)-1-aminoindan have no amphetamine-like activity.[3]
In spite of the preceding however, (R)-1-aminoindan is not lacking in pharmacological activity. Like rasagiline, it shows neuroprotective activity in some experimental models. In addition, (R)-1-aminoindan has been found to enhance striatal dopaminergic neurotransmission and to improve motor function independent of MAO inhibition in animal models of Parkinson's disease.
2-Aminoindan, a closely related positional isomer of 1-aminoindan, is known to inhibit the reuptake and induce the release of dopamine and norepinephrine and to produce psychostimulant-like effects in rodents, albeit with lower potency than amphetamine. However, rasagiline does not metabolize into this compound, and 1-aminoindan does not have the same effects.[4] [5] 1-Aminoindan has been found to inhibit the reuptake of norepinephrine 28-fold less potently than 2-aminoindan and to inhibit the reuptake of dopamine 300-fold less potently than 2-aminoindan, with values for dopamine reuptake inhibition in one study of 0.4μM for amphetamine, 3.3μM for 2-aminoindan, and 1mM for 1-aminoindan.[6] [7] In contrast to 2-aminoindan, which increased locomotor activity in rodents (+49%), 1-aminoindan suppressed locomotor activity (–69%). On the other hand however, 1-aminoindan has been found to enhance the psychostimulant-like effects of amphetamine in rodents.
(R)-1-Aminoindan is a 1-aminoindan derivative. It is specifically the (R)-enantiomer of 1-aminoindan, which is a racemic mixture of (R)- and (S)-enantiomers.[8] 1-Aminoindan is structurally related to 2-aminoindan. A number of derivatives of 1- and 2-aminoindan are known.