(R)-1-Aminoindane
Major metabolite of rasagiline
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(R)-1-Aminoindane ((R)-1-AI; developmental code name TVP-136 or TV-136), or (R)-1-aminoindan, is the major metabolite of the selective MAO-B inhibitor and antiparkinsonian agent rasagiline ((R)-N-propargyl-1-aminoindane).[1] In contrast to rasagiline, it lacks significant monoamine oxidase inhibition.[2][3] In addition, unlike selegiline and its amphetamine metabolites, it lacks monoamine reuptake-inhibiting and -releasing activities and associated amphetamine-like psychostimulant effects.[2][3][4] However, (R)-1-aminoindane retains neuroprotective effects and certain other activities.[2][3][4][5][6]
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| Other names | (R)-1-Aminoindan; (R)-(â)-1-Aminoindan; (R)-AI; (R)-1-AI; TVP-136; TV-136; (R)-(â)-1-Indanamine |
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| Formula | C9H11N |
| Molar mass | 133.194 g·molâ1 |
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Pharmacology
Pharmacodynamics
In contrast to rasagiline, (R)-1-aminoindane is either devoid of monoamine oxidase inhibition or shows only weak inhibition of MAO-B.[2][3] Unlike selegiline and its levomethamphetamine and levoamphetamine metabolites, rasagiline and (R)-1-aminoindane have no amphetamine-like activity.[2][3][4]
In spite of the preceding however, (R)-1-aminoindane is not lacking in pharmacological activity.[2][3] Like rasagiline, it shows neuroprotective activity in some experimental models.[2][3] In addition, (R)-1-aminoindane has been found to enhance striatal dopaminergic neurotransmission and to improve motor function independent of MAO inhibition in animal models of Parkinson's disease.[3]
2-Aminoindane, a closely related positional isomer of 1-aminoindane, 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.[1][5] However, rasagiline does not metabolize into this compound, and 1-aminoindane does not have the same effects.[1][5] 1-Aminoindane has been found to inhibit the reuptake of norepinephrine 28-fold less potently than 2-aminoindane and to inhibit the reuptake of dopamine 300-fold less potently than 2-aminoindan, with IC50 values for dopamine reuptake inhibition in one study of 0.4 μM for amphetamine, 3.3 μM for 2-aminoindan, and 1 mM for 1-aminoindane.[5][6][7] In contrast to 2-aminoindan, which increased locomotor activity in rodents (+49%), 1-aminoindane suppressed locomotor activity (â69%).[5] On the other hand however, 1-aminoindane has been found to enhance the psychostimulant-like effects of amphetamine in rodents.[6]
Chemistry
(R)-1-Aminoindane is a 1-aminoindane derivative.[1] It is specifically the (R)-enantiomer of 1-aminoindane, which is a racemic mixture of (R)- and (S)-enantiomers.[8] 1-Aminoindane is structurally related to 2-aminoindan.[1] A number of derivatives of 1- and 2-aminoindane are known.[1]