ORG-25935

ORG-25935
Identifiers
	IUPAC name 2-([(1R,2S)-6-Methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]methyl-methylamino)acetic acid;
CAS Number	949588-40-3;
PubChem CID	11717074;
ChemSpider	9891795;
UNII	55L20667O4;
Chemical and physical data
Formula	C21H25NO3
Molar mass	339.427 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(O)CN(C)C[C@@H]2[C@@H](c1c(cc(OC)cc1)CC2)c3ccccc3;
	InChI InChI=1S/C21H25NO3/c1-22(14-20(23)24)13-17-9-8-16-12-18(25-2)10-11-19(16)21(17)15-6-4-3-5-7-15/h3-7,10-12,17,21H,8-9,13-14H2,1-2H3,(H,23,24)/t17-,21+/m1/s1; Key:UEBBYLJZCHTLEG-UTKZUKDTSA-N;

ORG-25935, also known as SCH-900435 is a synthetic drug developed by Organon International, which acts as a selective inhibitor of the glycine transporter GlyT-1. In animal tests it reduces alcohol consumption and has analgesic and anticonvulsant effects, but it has mainly been studied for its antipsychotic properties, and in human trials it was shown to effectively counteract the effects of the dissociative drug ketamine.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]

References[edit]

^ Molander A, Lidö HH, Löf E, Ericson M, Söderpalm B. The glycine reuptake inhibitor Org 25935 decreases ethanol intake and preference in male wistar rats. Alcohol and Alcoholism. 2007 Jan-Feb;42(1):11-8. PMID 17098748
^ Morita K, Motoyama N, Kitayama T, Morioka N, Dohi T. Antinociceptive effects of glycine transporter inhibitors in neuropathic pain models in mice. Nihon Yakurigaku Zasshi. 2007 Dec;130(6):458-63. PMID 18079595
^ Lidö HH, Stomberg R, Fagerberg A, Ericson M, Söderpalm B. The glycine reuptake inhibitor org 25935 interacts with basal and ethanol-induced dopamine release in rat nucleus accumbens. Alcoholism: Clinical and Experimental Research. 2009 Jul;33(7):1151-7. PMID 19389199
^ Kalinichev M, Starr KR, Teague S, Bradford AM, Porter RA, Herdon HJ. Glycine transporter 1 (GlyT1) inhibitors exhibit anticonvulsant properties in the rat maximal electroshock threshold (MEST) test. Brain Research. 2010 May 17;1331:105-13. PMID 20303337
^ Vengeliene V, Leonardi-Essmann F, Sommer WH, Marston HM, Spanagel R. Glycine transporter-1 blockade leads to persistently reduced relapse-like alcohol drinking in rats. Biological Psychiatry. 2010 Oct 15;68(8):704-11. PMID 20655511
^ Musante V, Summa M, Cunha RA, Raiteri M, Pittaluga A. Pre-synaptic glycine GlyT1 transporter--NMDA receptor interaction: relevance to NMDA autoreceptor activation in the presence of Mg2+ ions. Journal of Neurochemistry. 2011 May;117(3):516-27. DOI 10.1111/j.1471-4159.2011.07223.x. PMID 21348870
^ Jardemark K, Marcus MM, Malmerfelt A, Shahid M, Svensson TH. Differential effects of AMPA receptor potentiators and glycine reuptake inhibitors on antipsychotic efficacy and prefrontal glutamatergic transmission. Psychopharmacology. 2011 Nov 9. PMID 22068461
^ D'Souza DC, Singh N, Elander J, Carbuto M, Pittman B, de Haes JU, Sjogren M, Peeters P, Ranganathan M, Schipper J. Glycine Transporter Inhibitor Attenuates the Psychotomimetic Effects of Ketamine in Healthy Males: Preliminary Evidence. Neuropsychopharmacology. 2011 Nov 23. DOI 10.1038/npp.2011.295. PMID 22113087

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[1] Molander A, Lidö HH, Löf E, Ericson M, Söderpalm B. The glycine reuptake inhibitor Org 25935 decreases ethanol intake and preference in male wistar rats. Alcohol and Alcoholism. 2007 Jan-Feb;42(1):11-8. PMID 17098748

[2] Morita K, Motoyama N, Kitayama T, Morioka N, Dohi T. Antinociceptive effects of glycine transporter inhibitors in neuropathic pain models in mice. Nihon Yakurigaku Zasshi. 2007 Dec;130(6):458-63. PMID 18079595

[3] Lidö HH, Stomberg R, Fagerberg A, Ericson M, Söderpalm B. The glycine reuptake inhibitor org 25935 interacts with basal and ethanol-induced dopamine release in rat nucleus accumbens. Alcoholism: Clinical and Experimental Research. 2009 Jul;33(7):1151-7. PMID 19389199

[4] Kalinichev M, Starr KR, Teague S, Bradford AM, Porter RA, Herdon HJ. Glycine transporter 1 (GlyT1) inhibitors exhibit anticonvulsant properties in the rat maximal electroshock threshold (MEST) test. Brain Research. 2010 May 17;1331:105-13. PMID 20303337

[5] Vengeliene V, Leonardi-Essmann F, Sommer WH, Marston HM, Spanagel R. Glycine transporter-1 blockade leads to persistently reduced relapse-like alcohol drinking in rats. Biological Psychiatry. 2010 Oct 15;68(8):704-11. PMID 20655511

[6] Musante V, Summa M, Cunha RA, Raiteri M, Pittaluga A. Pre-synaptic glycine GlyT1 transporter--NMDA receptor interaction: relevance to NMDA autoreceptor activation in the presence of Mg2+ ions. Journal of Neurochemistry. 2011 May;117(3):516-27. DOI 10.1111/j.1471-4159.2011.07223.x. PMID 21348870

[7] Jardemark K, Marcus MM, Malmerfelt A, Shahid M, Svensson TH. Differential effects of AMPA receptor potentiators and glycine reuptake inhibitors on antipsychotic efficacy and prefrontal glutamatergic transmission. Psychopharmacology. 2011 Nov 9. PMID 22068461

[8] D'Souza DC, Singh N, Elander J, Carbuto M, Pittman B, de Haes JU, Sjogren M, Peeters P, Ranganathan M, Schipper J. Glycine Transporter Inhibitor Attenuates the Psychotomimetic Effects of Ketamine in Healthy Males: Preliminary Evidence. Neuropsychopharmacology. 2011 Nov 23. DOI 10.1038/npp.2011.295. PMID 22113087

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ORG-25935

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Identifiers

IUPAC name 2-([(1R,2S)-6-Methoxy-1-phenyl-1,2,3,4-tetrahydronaphthalen-2-yl]methyl-methylamino)acetic acid
CAS Number	949588-40-3
PubChem CID	11717074
ChemSpider	9891795
UNII	55L20667O4
Chemical and physical data
Formula	C₂₁H₂₅NO₃
Molar mass	339.427 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(O)CN(C)C[C@@H]2[C@@H](c1c(cc(OC)cc1)CC2)c3ccccc3
InChI InChI=1S/C21H25NO3/c1-22(14-20(23)24)13-17-9-8-16-12-18(25-2)10-11-19(16)21(17)15-6-4-3-5-7-15/h3-7,10-12,17,21H,8-9,13-14H2,1-2H3,(H,23,24)/t17-,21+/m1/s1 Key:UEBBYLJZCHTLEG-UTKZUKDTSA-N