1-Aminoindane

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]

1-Aminoindane

Clinical data
Other names	1-AI; 1-Aminoindan; 1-Indanylamine; 1-Indanamine; (RS)-1-Aminoindane; (±)-1-Aminoindane
Identifiers
IUPAC name 2,3-dihydro-1H-inden-1-amine
CAS Number	34698-41-4
PubChem CID	123445
ChemSpider	110041
UNII	8UP8M3CGS8
ChEMBL	ChEMBL158574
CompTox Dashboard (EPA)	DTXSID20902754
Chemical and physical data
Formula	C9H11N
Molar mass	133.194 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CC2=CC=CC=C2C1N
InChI InChI=1S/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2 Key:XJEVHMGJSYVQBQ-UHFFFAOYSA-N

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.^[6] The (R)-enantiomer is (R)-1-aminoindan, which has pharmacological activity and is an active metabolite of the antiparkinsonian agent rasagiline.^[2][4][5]

A number of notable 1-aminoindane derivatives exist. These include the following:

• 1-Aminoindan-1,5-dicarboxylic acid (AIDA) – selective mGlu₁ receptor antagonist^[3][7]
• 1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) – selective mGlu₂ and mGlu₃ receptor antagonist^[7]
• AGN-1135 (racemic rasagiline; N-propargyl-1-aminoindane) – irreversible MAO-B inhibitor^[8][4]
• Indatraline (Lu 19-005) – serotonin–norepinephrine–dopamine reuptake inhibitor^[3]
• Ladostigil (TV-3326) – irreversible MAO-B inhibitor and reversible acetylcholinesterase and butyrylcholinesterase inhibitor^[9]
• Ozanimod (Zeposia) – sphingosine-1-phosphate receptor agonist
• Rasagiline (Azilect; N-propargyl-(R)-1-aminoindane) – selective irreversible MAO-B inhibitor and neuroprotective agent^[10]
• SU-11739 (AGN-1133; J-508; N-methyl-N-propargyl-1-aminoindane) – non-selective monoamine oxidase inhibitor and catecholamine releasing agent^{[8][10][11][12][13]}
• Zicronapine (Lu 31-130) – experimental atypical antipsychotic (D₁, D₂, and 5-HT_2A receptor antagonist)

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]