(R)-1-Aminoindane

Major metabolite of rasagiline September 2024 6 vanc (R)-1-Aminoindane (R)-1-Aminoindane.svg skin-invert-image 150px 10277-74-4 2733933 2015696 I17RC77CJ2 4573666 (R)-1-Aminoindan; (R)-(−)-1-Aminoindan; (R)-AI; (R)-1-AI; TVP-136; TV-136; (R)-(−)-1-Indanamine (1R)-2,3-dihydro-1H-inden-1-amine 9 11 1 C1CC2=CC=CC=C2[C@@H]1N 1S/C9H11N/c10-9-6-5-7-3-1-2-4-8(7)9/h1-4,9H,5-6,10H2/t9-/m1/s1 XJEVHMGJSYVQBQ-SECBINFHSA-N (R)-1-Aminoindane ((R)-1-AI; developmental code name TVP-136 or TV-136), or (R)-1-aminoindan, is the major metabolite of the selective MAO-B inhibitor and antiparkinsonian agent rasagiline ((R)-N-propargyl-1-aminoindane). In contrast to rasagiline, it lacks significant monoamine oxidase inhibition. In addition, unlike selegiline and its amphetamine metabolites, it lacks monoamine reuptake-inhibiting and -releasing activities and associated amphetamine-like psychostimulant effects. However, (R)-1-aminoindane retains neuroprotective effects and certain other activities. Pharmacology Pharmacodynamics In contrast to rasagiline, (R)-1-aminoindane is either devoid of monoamine oxidase inhibition or shows only weak inhibition of MAO-B.Chen JJ, Swope DM August 2005 Clinical pharmacology of rasagiline: a novel, second-generation propargylamine for the treatment of Parkinson disease http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=16027398 dead Journal of Clinical Pharmacology 45 8 878–894 10.1177/0091270005277935 16027398 24350277 https://archive.today/20120711214831/http://jcp.sagepub.com/cgi/pmidlookup?view=long&pmid=16027398 11 July 2012 subscription Müller T October 2014 Pharmacokinetic/pharmacodynamic evaluation of rasagiline mesylate for Parkinson's disease Expert Opinion on Drug Metabolism & Toxicology 10 10 1423–1432 10.1517/17425255.2014.943182 25196265 Unlike selegiline and its levomethamphetamine and levoamphetamine metabolites, rasagiline and (R)-1-aminoindane have no amphetamine-like activity.Schapira A, Bate G, Kirkpatrick P August 2005 Rasagiline Nature Reviews. Drug Discovery 4 8 625–626 10.1038/nrd1803 16106586 In spite of the preceding however, (R)-1-aminoindane is not lacking in pharmacological activity. Like rasagiline, it shows neuroprotective activity in some experimental models. In addition, (R)-1-aminoindane has been found to enhance striatal dopaminergic neurotransmission and to improve motor function independent of MAO inhibition in animal models of Parkinson's disease. 2-Aminoindane, a closely related positional isomer of 1-aminoindane, is known to inhibit the reuptake and induce the release of dopamine and norepinephrine and to produce psychostimulant-like effects in rodents, albeit with lower potency than amphetamine. However, rasagiline does not metabolize into this compound, and 1-aminoindane does not have the same effects.Pinterova N, Horsley RR, Palenicek T 2017 Synthetic Aminoindanes: A Summary of Existing Knowledge Frontiers in Psychiatry 8 236 10.3389/fpsyt.2017.00236 5698283 29204127 2-AI selectively inhibited just NET, and for SERT and DAT it has low potency. Apart from inhibitory actions on transporter molecules, aminoindanes have been shown to cause transporter-mediated release (reverse transport) of monoamines: MDAI released 5-HT and NE, 5-IAI released 5-HT and DA, and 2-AI released NE and DA (33). freeNovel Psychoactive Substances Brandt SD, Braithwaite RA, Evans-Brown M, Kicman AT 2013 Elsevier 978-0-12-415816-0 261–283 Aminoindane Analogues 10.1016/b978-0-12-415816-0.00011-0 1-Aminoindane has been found to inhibit the reuptake of norepinephrine 28-fold less potently than 2-aminoindane and to inhibit the reuptake of dopamine 300-fold less potently than 2-aminoindan, with IC50 half maximal inhibitory concentration values for dopamine reuptake inhibition in one study of 0.4μM for amphetamine, 3.3μM for 2-aminoindan, and 1mM for 1-aminoindane.MAO — the Mother of all Amine Oxidases Speiser Z, Levy R, Cohen S 1998 978-3-211-83037-6 Journal of Neural Transmission. Supplement 52 287–300 Effects of N-propargyl-1-(R)aminoindan (Rasagiline) in models of motor and cognition disorders 10.1007/978-3-7091-6499-0_29 9564629 Supplement: MAO — the Mother of all Amine OxidasesHorn AS, Snyder SH March 1972 Steric requirements for catecholamine uptake by rat brain synaptosomes: studies with rigid analogs of amphetamine The Journal of Pharmacology and Experimental Therapeutics 180 3 523–530 10.1016/S0022-3565(25)29135-2 5012779 In contrast to 2-aminoindan, which increased locomotor activity in rodents (+49%), 1-aminoindane suppressed locomotor activity (–69%). On the other hand however, 1-aminoindane has been found to enhance the psychostimulant-like effects of amphetamine in rodents. Chemistry (R)-1-Aminoindane is a 1-aminoindane derivative. It is specifically the (R)-enantiomer of 1-aminoindane, which is a racemic mixture of (R)- and (S)-enantiomers.1-Aminoindan https://pubchem.ncbi.nlm.nih.gov/compound/123445 1 September 2024 PubChem 1-Aminoindane is structurally related to 2-aminoindan. A number of derivatives of 1- and 2-aminoindane are known. References Category:1-Aminoindanes Category:Drugs with unknown mechanisms of action Category:Enantiopure drugs Category:Human drug metabolites Category:Neuroprotective agents