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Compound

SU-11739

Also called N-Methyl-N-2-propynylindanamine

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Overview

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

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. It is less selective for MAO-B inhibition than AGN-1135 (racemic rasagiline) or rasagiline. In addition to its MAOI activity, SU-11739 has been reported to have strong activity as a catecholamine releasing agent. Similarly to rasagiline, but unlike selegiline and desmethylselegiline, SU-11739 is not a monoaminergic activity enhancer (MAE).[3–7] WP

The drug is the racemic N-methylated analogue of rasagiline. It is also a ring-cyclized analogue of pargyline with about 20 times the MAOI potency of pargyline.[2][3][4][8] WP

SU-11739 was discovered before rasagiline and was patented in 1965. WP

Chemistry

Formula
C13H15N PC
CAS number
1875-49-6 PC
Molar mass (g/mol)
185.26 PC
IUPAC name (computed by PubChem)
N-methyl-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine PC
SMILES
CN(CC#C)C1CCC2=CC=CC=C12 PC
InChIKey
CSVGVHNFFZWQJU-UHFFFAOYSA-N PC
PubChem CID
15179
IUPAC name
N-methyl-N-prop-2-ynyl-2,3-dihydro-1H-inden-1-amine WP

Harm reduction information

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Sources

  1. Journal / agency Tipton KF, Fowler CJ, McCrodden JM, Strolin Benedetti M. 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. January 1983. doi:10.1042/bj2090235 · PMID 6847610 · PMC1154077
  2. Journal / agency Finberg JP. The discovery and development of rasagiline as a new anti-Parkinson medication. Journal of Neural Transmission. February 2020. doi:10.1007/s00702-020-02142-w · PMID 31974721
  3. Journal / agency Weinreb O, Amit T, Bar-Am O, Youdim MB. Rasagiline: a novel anti-Parkinsonian monoamine oxidase-B inhibitor with neuroprotective activity. Progress in Neurobiology. November 2010. doi:10.1016/j.pneurobio.2010.06.008 · PMID 20600573
  4. Journal / agency Youdim MB, Bakhle YS. Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness. British Journal of Pharmacology. January 2006. doi:10.1038/sj.bjp.0706464 · PMID 16402116 · PMC1760741
  5. Journal / agency Miklya I. Essential difference between the pharmacological spectrum of (-)-deprenyl and rasagiline. Pharmacol Rep. June 2014. doi:10.1016/j.pharep.2013.11.003 · PMID 24905523
  6. Journal / agency Miklya I. (-)-deprenil, az N-metilprogargilamin-1-aminoindan (J-508) és a J-508 dezmetil analógjának (rasagilin) összehasonlító farmakológiai analízise. Neuropsychopharmacol Hung. March 2008. PMID 18771016
  7. Journal / agency Yen TT, Dalló J, Knoll J. The aphrodisiac effect of low doses of (-) deprenyl in male rats. Pol J Pharmacol Pharm. 1982. PMID 6821215
  8. Journal / agency Huebner CF, Donoghue EM, Plummer AJ, Furness PA. N-methyl-n-2-propynyl-l-indanamine. A protent monoamine oxidase inhibitor. Journal of Medicinal Chemistry. November 1966. doi:10.1021/jm00324a009 · PMID 5972038

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