View source for SU-11739

{{Technical|date=September 2024}}
{{Short description|Monoamine oxidase inhibitor}}
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| CAS_number = 1875-49-6
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| PubChem = 15179
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| ChemSpiderID = 14447
| UNII = 37N2TO074R
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| synonyms = AGN-1133; J-508; ''N''-Methyl-''N''-propargyl-1-aminoindane; (±)-''N''-Methylrasagiline; (''RS'')-''N''-Methylrasagiline
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| IUPAC_name = ''N''-methyl-''N''-prop-2-ynyl-2,3-dihydro-1''H''-inden-1-amine
| C=13 | H=15 | N=1
| SMILES = CN(CC#C)C1CCC2=CC=CC=C12
| StdInChI = 1S/C13H15N/c1-3-10-14(2)13-9-8-11-6-4-5-7-12(11)13/h1,4-7,13H,8-10H2,2H3
| StdInChIKey = CSVGVHNFFZWQJU-UHFFFAOYSA-N
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'''SU-11739''' (other developmental code names '''AGN-1133''', '''J-508'''; also known as '''''N''-methyl-''N''-propargyl-1-aminoindane''')<ref name="TiptonFowlerMcCrodden1983">{{cite journal | vauthors = Tipton KF, Fowler CJ, McCrodden JM, Strolin Benedetti M | title = The enzyme-activated irreversible inhibition of type-B monoamine oxidase by 3-(4-[(3-chlorophenyl)methoxy]phenyl)-5-[(methylamino) methyl]-2-oxazolidinone methanesulphonate (compound MD 780236) and the enzyme-catalysed oxidation of this compound as competing reactions | journal = Biochem J | volume = 209 | issue = 1 | pages = 235–242 | date = January 1983 | pmid = 6847610 | pmc = 1154077 | doi = 10.1042/bj2090235 | url = | quote = Clorgyline hydrochloride was a gift from May and Baker, Dagenham, Essex, U.K. L-Deprenyl hydrochloride and compound J-508 [N-methyl-N-propargyl-L-aminoindane hydrochloride (compound AGN 1133; compound Su-11739)] were gifts from Professor J. Knoll, Department of Pharmacology, Semmelweis University of Medicine, Budapest, Hungary.}}</ref> is an [[experimental drug|experimental]] [[monoamine oxidase inhibitor]] (MAOI) that was never marketed.<ref name="Finberg2020">{{cite journal | vauthors = Finberg JP | title = The discovery and development of rasagiline as a new anti-Parkinson medication | journal = Journal of Neural Transmission | volume = 127 | issue = 2 | pages = 125–130 | date = February 2020 | pmid = 31974721 | doi = 10.1007/s00702-020-02142-w }}</ref><ref name="WeinrebAmitBar-Am2010">{{cite journal | vauthors = Weinreb O, Amit T, Bar-Am O, Youdim MB | title = Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity | journal = Progress in Neurobiology | volume = 92 | issue = 3 | pages = 330–344 | date = November 2010 | pmid = 20600573 | doi = 10.1016/j.pneurobio.2010.06.008 }}</ref><ref name="YoudimBakhle2006">{{cite journal | vauthors = Youdim MB, Bakhle YS | title = Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness | journal = British Journal of Pharmacology | volume = 147 | issue = Suppl 1 | pages = S287–S296 | date = January 2006 | pmid = 16402116 | pmc = 1760741 | doi = 10.1038/sj.bjp.0706464 }}</ref><ref name="Miklya2014">{{cite journal | vauthors = Miklya I | title = Essential difference between the pharmacological spectrum of (-)-deprenyl and rasagiline | journal = Pharmacol Rep | volume = 66 | issue = 3 | pages = 453–458 | date = June 2014 | pmid = 24905523 | doi = 10.1016/j.pharep.2013.11.003 | url = }}</ref>
It is a dual or [[binding selectivity|non-selective]] [[irreversible inhibitor|irreversible]] [[monoamine oxidase A]] (MAO-A) and [[monoamine oxidase B]] (MAO-B) [[enzyme inhibitor|inhibitor]], with preference for inhibition of MAO-B over MAO-A.<ref name="WeinrebAmitBar-Am2010" /><ref name="YoudimBakhle2006" /> It is less selective for MAO-B inhibition than [[AGN-1135]] (racemic rasagiline) or [[rasagiline]].<ref name="WeinrebAmitBar-Am2010" /> In addition to its MAOI activity, SU-11739 has been reported to have strong activity as a [[monoamine releasing agent|catecholamine releasing agent]].<ref name="Miklya2008">{{cite journal | vauthors = Miklya I | title = (-)-deprenil, az N-metilprogargilamin-1-aminoindan (J-508) és a J-508 dezmetil analógjának (rasagilin) összehasonlító farmakológiai analízise | trans-title = A comparison of the pharmacology of (-)-deprenyl to N-methylpropargylamine-1-aminoindane (J-508) and rasagiline, the desmethyl-analogue of J-508 | language = Hungarian | journal = Neuropsychopharmacol Hung | volume = 10 | issue = 1 | pages = 15–22 | date = March 2008 | pmid = 18771016 | doi = | url = https://mppt.hu/magazin/pdf/x-evfevfolyam-1-szam/a---deprenil-az-n.pdf}}</ref> Similarly to rasagiline, but unlike [[selegiline]] and [[desmethylselegiline]], SU-11739 is not a [[monoaminergic activity enhancer]] (MAE).<ref name="Miklya2014" /><ref name="YenDallóKnoll1982">{{cite journal | vauthors = Yen TT, Dalló J, Knoll J | title = The aphrodisiac effect of low doses of (-) deprenyl in male rats | journal = Pol J Pharmacol Pharm | volume = 34 | issue = 5–6 | pages = 303–308 | date = 1982 | pmid = 6821215 | doi = | url = }}</ref>
The drug is the [[racemic mixture|racemic]] ''N''-[[methyl group|methyl]]ated [[structural analog|analogue]] of [[rasagiline]].<ref name="Finberg2020" /><ref name="WeinrebAmitBar-Am2010" /><ref name="YoudimBakhle2006" /> It is also a [[ring (chemistry)|ring-cyclized]] analogue of [[pargyline]] with about 20{{nbsp}}times the MAOI [[potency (pharmacology)|potency]] of pargyline.<ref name="HuebnerDonoghuePlummer1966">{{cite journal | vauthors = Huebner CF, Donoghue EM, Plummer AJ, Furness PA | title = N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor | journal = Journal of Medicinal Chemistry | volume = 9 | issue = 6 | pages = 830–832 | date = November 1966 | pmid = 5972038 | doi = 10.1021/jm00324a009 }}</ref>
SU-11739 was discovered before rasagiline and was [[patent]]ed in 1965.<ref name="US3201470">{{cite patent | inventor = Huebner CF | country = US | number = 3201470 | title = | gdate = 17 August 1965 | assign = CIBA }}</ref>
==References==
{{Reflist}}
{{Monoamine metabolism modulators}}
{{Monoamine releasing agents}}
[[Category:1-Aminoindanes]]
[[Category:Abandoned drugs]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Monoamine releasing agents]]
[[Category:Propargyl compounds]]
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