1-Aminoindane

Chemical compound 1-Aminoindane.svg skin-invert-image 175px 34698-41-4 123445 110041 8UP8M3CGS8 158574 1-AI; 1-Aminoindan; 1-Indanylamine; 1-Indanamine; (RS)-1-Aminoindane; (±)-1-Aminoindane 2,3-dihydro-1H-inden-1-amine 9 11 1 C1CC2=CC=CC=C2C1N 1S/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 1-Aminoindane (1-AI), also known as 1-aminoindan, 1-indanylamine, or 1-indanamine, is an aminoindane. Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA Aminoindanes--the next wave of 'legal highs'? Drug Test Anal 3 7–8 479–482 2011 21748859 10.1002/dta.318 It is a positional isomer of 2-aminoindane. A variety of notable derivatives of 1- and 2-aminoindane are known. Pinterova N, Horsley RR, Palenicek T Synthetic Aminoindanes: A Summary of Existing Knowledge Frontiers in Psychiatry 8 236 2017 29204127 5698283 10.3389/fpsyt.2017.00236 free The (R)-enantiomer of 1-aminoindan, (R)-1-aminoindan, is pharmacologically active and is an active metabolite of the antiparkinsonian agent rasagiline. Chen JJ, Swope DM Clinical pharmacology of rasagiline: a novel, second-generation propargylamine for the treatment of Parkinson disease Journal of Clinical Pharmacology 45 8 878–894 August 2005 16027398 10.1177/0091270005277935 http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=16027398 24350277 https://archive.today/20120711214831/http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=16027398 11 July 2012 subscription Müller T Pharmacokinetic/pharmacodynamic evaluation of rasagiline mesylate for Parkinson's disease Expert Opinion on Drug Metabolism & Toxicology 10 10 1423–1432 October 2014 25196265 10.1517/17425255.2014.943182 1-Aminoindane was used in the synthesis of an agent that is called Pevonedistat.Lednicer D 2015 Antineoplastic drugs: organic synthesis John Wiley & Sons 978-1-118-89256-5 Pharmacology Through its (R)-enantiomer (R)-1-aminoindane, 1-aminoindane has pharmacological activity. It specifically shows neuroprotective and catecholamine-modulating actions. Chemistry 1-Aminoindane is an aminoindane. It is a racemic mixture of (R)- and (S)-enantiomers.1-Aminoindan PubChem https://pubchem.ncbi.nlm.nih.gov/compound/123445 1 September 2024 The (R)-enantiomer is (R)-1-aminoindan, which has pharmacological activity and is an active metabolite of the antiparkinsonian agent rasagiline. Derivatives A number of notable 1-aminoindane derivatives exist. These include the following: 1-Aminoindan-1,5-dicarboxylic acid (AIDA) – selective mGlu1 receptor antagonist Bräuner-Osborne H, Egebjerg J, Nielsen EO, Madsen U, Krogsgaard-Larsen P Ligands for glutamate receptors: design and therapeutic prospects J Med Chem 43 14 2609–2645 July 2000 10893301 10.1021/jm000007r 1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) – selective mGlu2 and mGlu3 receptor antagonist AGN-1135 (racemic rasagiline; N-propargyl-1-aminoindane) – irreversible MAO-B inhibitor Indatraline (Lu 19-005) – serotonin–norepinephrine–dopamine reuptake inhibitor Vilums M, Heuberger J, Heitman LH, IJzerman AP Indanes--Properties, Preparation, and Presence in Ligands for G Protein Coupled Receptors Med Res Rev 35 6 1097–1126 November 2015 26018667 10.1002/med.21352 Ladostigil (TV-3326) – irreversible MAO-B inhibitor and reversible acetylcholinesterase and butyrylcholinesterase inhibitor Weinreb O, Amit T, Bar-Am O, Youdim MB 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 April 2012 22280345 10.2174/138945012799499794 Ozanimod (Zeposia) – sphingosine-1-phosphate receptor agonist Rasagiline (Azilect; N-propargyl-(R)-1-aminoindane) – selective irreversible MAO-B inhibitor and neuroprotective agent Weinreb O, Amit T, Bar-Am O, Youdim MB Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity Prog Neurobiol 92 3 330–344 November 2010 20600573 10.1016/j.pneurobio.2010.06.008 SU-11739 (AGN-1133; J-508; N-methyl-N-propargyl-1-aminoindane) – non-selective monoamine oxidase inhibitor and catecholamine releasing agent Finberg JP The discovery and development of rasagiline as a new anti-Parkinson medication Journal of Neural Transmission 127 2 125–130 February 2020 31974721 10.1007/s00702-020-02142-w Youdim MB, Bakhle YS Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness British Journal of Pharmacology 147 Suppl 1 S287–S296 January 2006 16402116 1760741 10.1038/sj.bjp.0706464 Huebner CF, Donoghue EM, Plummer AJ, Furness PA N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor Journal of Medicinal Chemistry 9 6 830–832 November 1966 5972038 10.1021/jm00324a009 Miklya I (−)-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 Hungarian Neuropsychopharmacol Hung 10 1 15–22 March 2008 18771016 https://mppt.hu/magazin/pdf/x-evfevfolyam-1-szam/a---deprenil-az-n.pdf Zicronapine (Lu 31-130) – 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. A variety of notable 2-aminoindane derivatives also exist. Pinterova N, Horsley RR, Palenicek T Synthetic Aminoindanes: A Summary of Existing Knowledge Frontiers in Psychiatry 8 236 2017 29204127 5698283 10.3389/fpsyt.2017.00236 free References * Category:Drugs with unknown mechanisms of action Category:Neuroprotective agents