1-Aminoindane
Chemical compound
From Wikipedia, the free encyclopedia
1-Aminoindane (1-AI), also known as 1-aminoindan, 1-indanylamine, or 1-indanamine, is an aminoindane.[1] It is a positional isomer of 2-aminoindane.[1] A variety of notable derivatives of 1- and 2-aminoindane are known.[1][2][3] The (R)-enantiomer of 1-aminoindan, (R)-1-aminoindan, is pharmacologically active and is an active metabolite of the antiparkinsonian agent rasagiline.[2][4][5]
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| Other names | 1-AI; 1-Aminoindan; 1-Indanylamine; 1-Indanamine; (RS)-1-Aminoindane; (±)-1-Aminoindane |
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| Formula | C9H11N |
| Molar mass | 133.194 g·molâ1 |
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1-Aminoindane was used in the synthesis of an agent that is called Pevonedistat.[6]
Pharmacology
Through its (R)-enantiomer (R)-1-aminoindane, 1-aminoindane has pharmacological activity.[2][4][5] It specifically shows neuroprotective and catecholamine-modulating actions.[2][4][5]
Chemistry
1-Aminoindane is an aminoindane.[1] It is a racemic mixture of (R)- and (S)-enantiomers.[7] The (R)-enantiomer is (R)-1-aminoindan, which has pharmacological activity and is an active metabolite of the antiparkinsonian agent rasagiline.[2][4][5]
Derivatives
A number of notable 1-aminoindane derivatives exist. These include the following:
- 1-Aminoindan-1,5-dicarboxylic acid (AIDA) â selective mGlu1 receptor antagonist[3][8]
- 1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) â selective mGlu2 and mGlu3 receptor antagonist[8]
- AGN-1135 (racemic rasagiline; N-propargyl-1-aminoindane) â irreversible MAO-B inhibitor[9][4]
- Indatraline (Lu 19-005) â serotoninânorepinephrineâdopamine reuptake inhibitor[3]
- Ladostigil (TV-3326) â irreversible MAO-B inhibitor and reversible acetylcholinesterase and butyrylcholinesterase inhibitor[10]
- Ozanimod (Zeposia) â sphingosine-1-phosphate receptor agonist
- Rasagiline (Azilect; N-propargyl-(R)-1-aminoindane) â selective irreversible MAO-B inhibitor and neuroprotective agent[11]
- SU-11739 (AGN-1133; J-508; N-methyl-N-propargyl-1-aminoindane) â non-selective monoamine oxidase inhibitor and catecholamine releasing agent[9][11][12][13][14]
- Zicronapine (Lu 31-130) â experimental atypical antipsychotic (D1, D2, and 5-HT2A receptor antagonist)
Analogues
Jimscaline, 2CB-Ind, and AMMI are derivatives of 1-aminomethylindane, an indane- and amine-containing compound closely related to 1-aminoindane.
1-Aminoindane is a positional isomer of 2-aminoindane.[1] A variety of notable 2-aminoindane derivatives also exist.[2][1]