1-Aminoindane
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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·mol−1 |
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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
[edit]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
[edit]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
[edit]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
[edit]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
[edit]- 1 2 3 4 5 6 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.
- 1 2 3 4 5 6 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.
- 1 2 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.
- 1 2 3 4 5 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.
{{cite journal}}: CS1 maint: deprecated archival service (link) - 1 2 3 4 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.
- ↑ Lednicer D (2015). Antineoplastic drugs: organic synthesis. John Wiley & Sons. ISBN 978-1-118-89256-5.
- ↑ "1-Aminoindan". PubChem. Retrieved 1 September 2024.
- 1 2 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.
- 1 2 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.
- ↑ 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.
- 1 2 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.