SU-11739

SU-11739
Clinical data
Other names	AGN-1133; J-508; N-Methyl-N-propargyl-1-aminoindane; (±)-N-Methylrasagiline; (RS)-N-Methylrasagiline
Identifiers
	IUPAC name N-methyl-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine;
CAS Number	1875-49-6;
PubChem CID	15179;
ChemSpider	14447;
UNII	37N2TO074R;
CompTox Dashboard (EPA)	DTXSID40953900 ;
Chemical and physical data
Formula	C13H15N
Molar mass	185.270 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(CC#C)C1CCC2=CC=CC=C12;
	InChI InChI=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; Key:CSVGVHNFFZWQJU-UHFFFAOYSA-N;

SU-11739 (other developmental code names AGN-1133, J-508; also known as N-methyl-N-propargyl-1-aminoindane)^[1] is an experimental monoamine oxidase inhibitor (MAOI) that was never marketed.^[2]^[3]^[4]^[5]

It is a dual or non-selective irreversible monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) inhibitor, with preference for inhibition of MAO-B over MAO-A.^[3]^[4] It is less selective for MAO-B inhibition than AGN-1135 (racemic rasagiline) or rasagiline.^[3] In addition to its MAOI activity, SU-11739 has been reported to have strong activity as a catecholamine releasing agent.^[6] Similarly to rasagiline, but unlike selegiline and desmethylselegiline, SU-11739 is not a monoaminergic activity enhancer (MAE).^[5]

The drug is the racemic N-methylated analogue of rasagiline.^[2]^[3]^[4] It is also a ring-cyclized analogue of pargyline with about 20 times the MAOI potency of pargyline.^[7]

SU-11739 was discovered before rasagiline and was patented in 1965.^[8]

References

^ Tipton KF, Fowler CJ, McCrodden JM, Strolin Benedetti M (January 1983). "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". Biochem J. 209 (1): 235–242. doi:10.1042/bj2090235. PMC 1154077. PMID 6847610. 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.
^ ^a ^b 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.
^ ^a ^b ^c ^d Weinreb O, Amit T, Bar-Am O, Youdim MB (November 2010). "Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity". Progress in Neurobiology. 92 (3): 330–344. doi:10.1016/j.pneurobio.2010.06.008. PMID 20600573.
^ ^a ^b ^c 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.
^ ^a ^b Miklya I (June 2014). "Essential difference between the pharmacological spectrum of (-)-deprenyl and rasagiline". Pharmacol Rep. 66 (3): 453–458. doi:10.1016/j.pharep.2013.11.003. PMID 24905523.
^ 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.
^ 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.
^ US 3201470, Huebner CF, issued 17 August 1965, assigned to CIBA

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[TiptonFowlerMcCrodden1983-1] Tipton KF, Fowler CJ, McCrodden JM, Strolin Benedetti M (January 1983). "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". Biochem J. 209 (1): 235–242. doi:10.1042/bj2090235. PMC 1154077. PMID 6847610. 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.

[Finberg2020-2] 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.

[WeinrebAmitBar-Am2010-3] Weinreb O, Amit T, Bar-Am O, Youdim MB (November 2010). "Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity". Progress in Neurobiology. 92 (3): 330–344. doi:10.1016/j.pneurobio.2010.06.008. PMID 20600573.

[YoudimBakhle2006-4] 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.

[Miklya2014-5] Miklya I (June 2014). "Essential difference between the pharmacological spectrum of (-)-deprenyl and rasagiline". Pharmacol Rep. 66 (3): 453–458. doi:10.1016/j.pharep.2013.11.003. PMID 24905523.

[Miklya2008-6] 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.

[HuebnerDonoghuePlummer1966-7] 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.

[US3201470-8] US 3201470, Huebner CF, issued 17 August 1965, assigned to CIBA

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