1-Aminoindane

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

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]}

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]}

References

1. Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Test Anal. 3 (7–8): 479–482. doi:10.1002/dta.318. PMID   21748859.
2. Pinterova N, Horsley RR, Palenicek T (2017). "Synthetic Aminoindanes: A Summary of Existing Knowledge". Frontiers in Psychiatry. 8 236. doi: 10.3389/fpsyt.2017.00236 . PMC   5698283 . PMID   29204127.
3. Vilums M, Heuberger J, Heitman LH, IJzerman AP (November 2015). "Indanes--Properties, Preparation, and Presence in Ligands for G Protein Coupled Receptors". Med Res Rev. 35 (6): 1097–1126. doi:10.1002/med.21352. PMID   26018667.
4. Chen JJ, Swope DM (August 2005). "Clinical pharmacology of rasagiline: a novel, second-generation propargylamine for the treatment of Parkinson disease". Journal of Clinical Pharmacology. 45 (8): 878–894. doi:10.1177/0091270005277935. PMID   16027398. S2CID   24350277. Archived from the original on 11 July 2012.
5. Müller T (October 2014). "Pharmacokinetic/pharmacodynamic evaluation of rasagiline mesylate for Parkinson's disease". Expert Opinion on Drug Metabolism & Toxicology. 10 (10): 1423–1432. doi:10.1517/17425255.2014.943182. PMID   25196265.
6. "1-Aminoindan". PubChem. Retrieved 1 September 2024.
7. Bräuner-Osborne H, Egebjerg J, Nielsen EO, Madsen U, Krogsgaard-Larsen P (July 2000). "Ligands for glutamate receptors: design and therapeutic prospects". J Med Chem. 43 (14): 2609–2645. doi:10.1021/jm000007r. PMID   10893301.
8. Finberg JP (February 2020). "The discovery and development of rasagiline as a new anti-Parkinson medication". Journal of Neural Transmission. 127 (2): 125–130. doi:10.1007/s00702-020-02142-w. PMID   31974721.
9. Weinreb O, Amit T, Bar-Am O, Youdim MB (April 2012). "Ladostigil: a novel multimodal neuroprotective drug with cholinesterase and brain-selective monoamine oxidase inhibitory activities for Alzheimer's disease treatment". Curr Drug Targets. 13 (4): 483–494. doi:10.2174/138945012799499794. PMID   22280345.
10. Weinreb O, Amit T, Bar-Am O, Youdim MB (November 2010). "Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity". Prog Neurobiol. 92 (3): 330–344. doi:10.1016/j.pneurobio.2010.06.008. PMID   20600573.
11. Youdim MB, Bakhle YS (January 2006). "Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness". British Journal of Pharmacology. 147 (Suppl 1): S287 –S296. doi:10.1038/sj.bjp.0706464. PMC   1760741 . PMID   16402116.
12. Huebner CF, Donoghue EM, Plummer AJ, Furness PA (November 1966). "N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor". Journal of Medicinal Chemistry. 9 (6): 830–832. doi:10.1021/jm00324a009. PMID   5972038.
13. Miklya I (March 2008). "(-)-deprenil, az N-metilprogargilamin-1-aminoindan (J-508) és a J-508 dezmetil analógjának (rasagilin) összehasonlító farmakológiai analízise" [A comparison of the pharmacology of (-)-deprenyl to N-methylpropargylamine-1-aminoindane (J-508) and rasagiline, the desmethyl-analogue of J-508](PDF). Neuropsychopharmacol Hung (in Hungarian). 10 (1): 15–22. PMID   18771016.