Chemistry: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 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) – selective mGlu1 receptor antagonist[3][8]
- 1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) – selective mGlu2 and mGlu3 receptor antagonist[8]
- AGN-1135 (racemic rasagiline; N-propargyl-1-aminoindane) – irreversible MAO-B inhibitor[9][4]
- Indatraline (Lu 19-005) – serotonin–norepinephrine–dopamine reuptake inhibitor[3]
- Ladostigil (TV-3326) – irreversible MAO-B inhibitor and reversible acetylcholinesterase and butyrylcholinesterase inhibitor[10]
- Ozanimod (Zeposia) – sphingosine-1-phosphate receptor agonist
- Rasagiline (Azilect; N-propargyl-(R)-1-aminoindane) – selective irreversible MAO-B inhibitor and neuroprotective agent[11]
- SU-11739 (AGN-1133; J-508; N-methyl-N-propargyl-1-aminoindane) – non-selective monoamine oxidase inhibitor and catecholamine releasing agent[9][11][12][13][14]
- 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.[1] A variety of notable 2-aminoindane derivatives also exist.[2][1]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 "Aminoindanes--the next wave of 'legal highs'?". Drug Test Anal 3 (7–8): 479–482. 2011. doi:10.1002/dta.318. PMID 21748859.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Synthetic Aminoindanes: A Summary of Existing Knowledge". Frontiers in Psychiatry 8. 2017. doi:10.3389/fpsyt.2017.00236. PMID 29204127.
- ↑ 3.0 3.1 3.2 "Indanes--Properties, Preparation, and Presence in Ligands for G Protein Coupled Receptors". Med Res Rev 35 (6): 1097–1126. November 2015. doi:10.1002/med.21352. PMID 26018667.
- ↑ 4.0 4.1 4.2 4.3 4.4 "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. doi:10.1177/0091270005277935. PMID 16027398. http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=16027398.
- ↑ 5.0 5.1 5.2 5.3 "Pharmacokinetic/pharmacodynamic evaluation of rasagiline mesylate for Parkinson's disease". Expert Opinion on Drug Metabolism & Toxicology 10 (10): 1423–1432. October 2014. doi:10.1517/17425255.2014.943182. PMID 25196265.
- ↑ Antineoplastic drugs: organic synthesis. John Wiley & Sons. 2015. ISBN 978-1-118-89256-5.
- ↑ "1-Aminoindan". https://pubchem.ncbi.nlm.nih.gov/compound/123445.
- ↑ 8.0 8.1 "Ligands for glutamate receptors: design and therapeutic prospects". J Med Chem 43 (14): 2609–2645. July 2000. doi:10.1021/jm000007r. PMID 10893301.
- ↑ 9.0 9.1 "The discovery and development of rasagiline as a new anti-Parkinson medication". Journal of Neural Transmission 127 (2): 125–130. February 2020. doi:10.1007/s00702-020-02142-w. PMID 31974721.
- ↑ "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. doi:10.2174/138945012799499794. PMID 22280345.
- ↑ 11.0 11.1 "Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity". Prog Neurobiol 92 (3): 330–344. November 2010. doi:10.1016/j.pneurobio.2010.06.008. PMID 20600573.
- ↑ "Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness". British Journal of Pharmacology 147 (Suppl 1): S287–S296. January 2006. doi:10.1038/sj.bjp.0706464. PMID 16402116.
- ↑ "N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor". Journal of Medicinal Chemistry 9 (6): 830–832. November 1966. doi:10.1021/jm00324a009. PMID 5972038.
- ↑ "(−)-deprenil, az N-metilprogargilamin-1-aminoindan (J-508) és a J-508 dezmetil analógjának (rasagilin) összehasonlító farmakológiai analízise" (in Hungarian). Neuropsychopharmacol Hung 10 (1): 15–22. March 2008. PMID 18771016. https://mppt.hu/magazin/pdf/x-evfevfolyam-1-szam/a---deprenil-az-n.pdf.
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