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RS-127445

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Chemical compound

Pharmaceutical compound

RS-127445
Clinical data

Other names	RS-127,445; MT500; MT-500
Identifiers
IUPAC name 4-(4-fluoro-1-naphthyl)-6-isopropylpyrimidin-2-amine
CAS Number	199864-87-4
PubChemCID	196968
IUPHAR/BPS	188
ChemSpider	170590
UNII	0JAU3P8OBM
ChEMBL	ChEMBL473186
CompTox Dashboard(EPA)	DTXSID60941960
Chemical and physical data
Formula	C₁₇H₁₆FN₃
Molar mass	281.334 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Nc3nc(C(C)C)cc(n3)-c(cc2)c1ccccc1c2F
InChI InChI=1S/C17H16FN3/c1-10(2)15-9-16(21-17(19)20-15)13-7-8-14(18)12-6-4-3-5-11(12)13/h3-10H,1-2H3,(H2,19,20,21) Key:ZZZQXCUPAJFVBN-UHFFFAOYSA-N
(verify)

RS-127445, also known asMT-500, is a drug which acts as a potent and selectiveantagonist at theserotonin 5-HT_2B receptor, with around 1,000-foldselectivity over the closely related5-HT_2A and5-HT_2C receptors.^[1] The role of the 5-HT_2B receptor in the body is still poorly understood, and RS-127445 has been a useful tool in unravelling the function of the various systems in which this receptor is expressed.^[2]^[3]^[4] The drug was under development for potential use as apharmaceutical drug byRoche and reachedphase 1 clinical trials but was discontinued for unknown reasons.^[5]^[6]

RS-127445 has been found to diminish thehead-twitch response, a behavioral proxy ofpsychedelic effects, induced by the psychedelic drugLSD in rats but not in mice.^[7] It also blocked the persistentantidepressant-like effects produced by LSD in rats.^[7]

References

[edit]

^Bonhaus DW, Flippin LA, Greenhouse RJ, Jaime S, Rocha C, Dawson M, et al. (July 1999)."RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist".British Journal of Pharmacology.127 (5):1075–82.doi:10.1038/sj.bjp.0702632.PMC 1566110.PMID 10455251.
^Launay JM, Hervé P, Peoc'h K, Tournois C, Callebert J, Nebigil CG, et al. (October 2002)."Function of the serotonin 5-hydroxytryptamine 2B receptor in pulmonary hypertension"(PDF).Nature Medicine.8 (10):1129–35.doi:10.1038/nm764.PMID 12244304.S2CID 20736218.
^Kelly CR, Sharif NA (June 2006). "Pharmacological evidence for a functional serotonin-2B receptor in a human uterine smooth muscle cell line".The Journal of Pharmacology and Experimental Therapeutics.317 (3):1254–61.doi:10.1124/jpet.105.100172.PMID 16517693.S2CID 6604193.
^Mbaki Y, Ramage AG (October 2008)."Investigation of the role of 5-HT2 receptor subtypes in the control of the bladder and the urethra in the anaesthetized female rat".British Journal of Pharmacology.155 (3):343–56.doi:10.1038/bjp.2008.273.PMC 2567885.PMID 18604238.
^"Delving into the Latest Updates on MT-500 with Synapse".Synapse. 21 November 2024. Retrieved30 November 2024.
^Wang Q, Zhou Y, Huang J, Huang N (January 2021)."Structure, Function, and Pharmaceutical Ligands of 5-Hydroxytryptamine 2B Receptor".Pharmaceuticals (Basel).14 (2): 76.doi:10.3390/ph14020076.PMC 7909583.PMID 33498477.
^^a ^bBouloufa A, Delcourte S, Rovera R, Mouledous L, Guiard B, Haddjeri N (18 August 2025)."327. 5-HT2B Receptors Modulate the Antidepressant-like Response of the Psychedelic LSD in Rat But Not in Mice".International Journal of Neuropsychopharmacology.28 (Supplement_2):ii117 –ii118.doi:10.1093/ijnp/pyaf052.234.ISSN 1461-1457.PMC 12359452.

Serotonin receptor modulators

5-HT₁

5-HT_1A

Agonists:4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g.,etoperidone,hydroxynefazodone,nefazodone,trazodone,triazoledione,vilazodone,vortioxetine) Atypical antipsychotics (e.g.,aripiprazole,asenapine,brexpiprazole,cariprazine,clozapine,lurasidone,quetiapine,ziprasidone) Azapirones (e.g.,buspirone,eptapirone,gepirone,perospirone,tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine,cabergoline,dihydroergotamine,ergotamine,lisuride,LSD,methylergometrine (methylergonovine),methysergide,pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT,5-MeO-DMT,5-MT,bufotenin,DMT,indorenate,N-Me-5-HT,psilocin,psilocybin) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine
Positive allosteric modulators:Oleamide
Antagonists:Atypical antipsychotics (e.g.,iloperidone,risperidone,sertindole) AV965 Beta blockers (e.g.,alprenolol,carteolol,cyanopindolol,iodocyanopindolol,isamoltane,oxprenolol,penbutolol,pindobind,pindolol,propranolol,tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g.,metergoline) FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
Unknown/unsorted:Acetryptine Carvedilol Ergolines (e.g.,ergometrine (ergonovine))

5-HT_1B

Agonists:Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB,6-MAPB,BK-5-MAPB,BK-6-MAPB) Benzothiophenes (e.g.,5-MAPBT,6-MAPBT,BK-5-MAPBT) CGS-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) mCPP Methylenedioxyphenethylamines (e.g.,MDMA,methylone) PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan,donitriptan,eletriptan,sumatriptan,zolmitriptan) TFMPP Tryptamines (e.g.,5-BT,5-CT,5-MT,DMT) Vortioxetine
Antagonists:AR-A000002 Beta blockers (e.g.,alprenolol,carteolol,isamoltane,oxprenolol,penbutolol,propranolol,tertatolol) Elzasonan Ergolines (e.g.,metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine
Unknown/unsorted:Ergolines (e.g.,cabergoline,ergometrine (ergonovine),lisuride)

5-HT_1D

Agonists:CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine,cabergoline,dihydroergotamine,ergotamine,LSD,methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan,avitriptan,donitriptan,eletriptan,frovatriptan,naratriptan,rizatriptan,sumatriptan,zolmitriptan) Tryptamines (e.g.,5-BT,5-CT,5-Et-DMT,5-MT,5-(nonyloxy)tryptamine,DMT)
Antagonists:Alniditan BRL-15572 Elzasonan Ergolines (e.g.,metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone
Unknown/unsorted:Acetryptine Ergolines (e.g.,lisuride,lysergol,pergolide)

5-HT_1E

Agonists:BRL-54443 Ergolines (e.g.,methysergide) Serotonin (5-HT) Triptans (e.g.,eletriptan) Tryptamines (e.g.,tryptamine)
Antagonists:Metitepine (methiothepin)
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine),lysergol,methylergometrine (methylergonovine)

5-HT_1F

Agonists:BRL-54443 CP-122288 Ergolines (e.g.,bromocriptine,lysergol,methylergometrine (methylergonovine)methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g.,eletriptan,naratriptan,sumatriptan) Tryptamines (e.g.,5-MT)
Antagonists:Metitepine (methiothepin) Mianserin

5-HT₂

5-HT_2A

Agonists: 25H/NB series (e.g.,25I-NBF,25I-NBMD,25I-NBOH,25I-NBOMe,25B-NBOMe,25C-NBOMe,25TFM-NBOMe,2CBCB-NBOMe,25CN-NBOH,2CBFly-NBOMe) 2Cs (e.g.,2C-B,2C-E,2C-I,2C-T-2,2C-T-7,2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET,5-MeO-DiPT,5-MeO-DMT,5-MeO-DPT,5-MT) α-Alkyltryptamines (e.g.,5-Cl-αMT,5-Fl-αMT,5-MeO-αET,5-MeO-αMT,α-Me-5-HT,αET,αMT) AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g.,DOB,DOC,DOI,DOM) Efavirenz Ergolines (e.g.,1P-LSD,ALD-52,bromocriptine,cabergoline,ergine (LSA),ergometrine (ergonovine),ergotamine,lisuride,LA-SS-Az,LSB,LSD,LSD-Pip,LSH,LSP,methylergometrine (methylergonovine),pergolide) Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g.,lophophine,mescaline) Piperazines (e.g.,BZP,quipazine,TFMPP) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g.,5-BT,5-CT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine)
Positive allosteric modulators:CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide
Antagonists:5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g.,cyproheptadine,hydroxyzine,ketotifen,perlapine) AMDA Atypical antipsychotics (e.g.,amperozide,aripiprazole,asenapine,blonanserin,brexpiprazole,carpipramine,clocapramine,clorotepine,clozapine,fluperlapine,gevotroline,iloperidone,lurasidone,melperone,mosapramine,ocaperidone,olanzapine,paliperidone,quetiapine,risperidone,sertindole,zicronapine,ziprasidone,zotepine) Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone,hydroxynefazodone,lubazodone,mepiprazole,nefazodone,triazoledione,trazodone) SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine,aptazapine,esmirtazapine,maprotiline,mianserin,mirtazapine) Tricyclic antidepressants (e.g.,amitriptyline) Typical antipsychotics (e.g.,chlorpromazine,fluphenazine,haloperidol,loxapine,perphenazine,pimozide,pipamperone,prochlorperazine,setoperone,spiperone,spiramide,thioridazine,thiothixene,trifluoperazine) Volinanserin Xylamidine Yohimbine
Unknown/unsorted:Ergolines (e.g.,dihydroergotamine,nicergoline)

5-HT_2B

Agonists:4-Methylaminorex Aminorex Amphetamines (e.g.,chlorphentermine,cloforex,dexfenfluramine,fenfluramine,levofenfluramine,norfenfluramine) BW-723C86 DOx (e.g.,DOB,DOC,DOI,DOM) Ergolines (e.g.,cabergoline,dihydroergocryptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) Piperazines (e.g.,TFMPP) PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g.,5-BT,5-CT,5-MT,α-Me-5-HT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine)
Antagonists:Agomelatine Atypical antipsychotics (e.g.,amisulpride,aripiprazole,asenapine,brexpiprazole,cariprazine,clozapine,N-desalkylquetiapine (norquetiapine),N-desmethylclozapine (norclozapine),olanzapine,pipamperone,quetiapine,risperidone,ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g.,amesergide,bromocriptine,lisuride,LY-53857,LY-272015,mesulergine) Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g.,amoxapine,mianserin,mirtazapine) Trazodone Typical antipsychotics (e.g.,chlorpromazine) TIK-301 Yohimbine
Unknown/unsorted:Ergolines (e.g.,ergometrine (ergonovine))

5-HT_2C

Agonists:2Cs (e.g.,2C-B,2C-E,2C-I,2C-T-2,2C-T-7,2C-T-21) 5-Methoxytryptamines (5-MeO-DET,5-MeO-DiPT,5-MeO-DMT,5-MeO-DPT,5-MT) α-Alkyltryptamines (e.g.,5-Cl-αMT,5-Fl-αMT,5-MeO-αET,5-MeO-αMT,α-Me-5-HT,αET,αMT) A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g.,DOB,DOC,DOI,DOM) Ergolines (e.g.,ALD-52,cabergoline,dihydroergotamine,ergine (LSA),ergotamine,lisuride,LA-SS-Az,LSB,LSD,LSD-Pip,LSH,LSP,pergolide) Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine),MDMA (midomafetamine),MDOH,MMDA) MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine,mescaline) Piperazines (e.g.,aripiprazole,BZP,mCPP,quipazine,TFMPP) PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT,5-CT,bufotenin,DET,DiPT,DMT,DPT,psilocin,psilocybin,tryptamine) Vabicaserin WAY-629 WAY-161503 YM-348
Positive allosteric modulators:CTW0415 CYD-1-79 JPC0323 Oleamide PNU-69176E VA012 VA240
Antagonists:Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine,clorotepine,clozapine,fluperlapine,iloperidone,melperone,olanzapine,paliperidone,quetiapine,risperidone,sertindole,ziprasidone,zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide,bromocriptine,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine,aptazapine,esmirtazapine,maprotiline,mianserin,mirtazapine) TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline,nortriptyline) Typical antipsychotics (e.g.,chlorpromazine,loxapine,pimozide,pipamperone,thioridazine) Xylamidine
Unknown/unsorted:Efavirenz Ergolines (e.g.,ergometrine (ergonovine),methylergometrine (methylergonovine))

5-HT₃_–7

5-HT₃

Agonists:Alcohols (e.g.,butanol,ethanol (alcohol),trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g.,BZP,mCPP,quipazine) RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g.,2-Me-5-HT,5-CT,bufotenidine (5-HTQ)) Volatiles/gases (e.g.,halothane,isoflurane,toluene,trichloroethane) YM-31636
Positive allosteric modulators:5-Aminoindole 5-Chloroindole 5-Hydroxyindole Catechol Chloroform meta-Chlorophenylbiguanide (mCPBG) Colchicine Ethanol (alcohol) Halothane Indole Isoflurane TMPPAA
Antagonists:Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g.,clozapine,olanzapine,quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine,mianserin,mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g.,loxapine) Volatiles/gases (e.g.,nitrous oxide,sevoflurane,xenon) Vortioxetine Zacopride Zatosetron
Negative allosteric modulators:Bupropion Colchicine Hydroxybupropion
Unknown/unsorted:LY-53857 Piperazines (e.g.,naphthylpiperazine)

5-HT₄

Agonists:5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride
Antagonists:GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A

Agonists:Ergolines (e.g.,2-Br-LSD (BOL-148),ergotamine,LSD) Serotonin (5-HT) Tryptamines (e.g.,5-CT) UCSF648 Valerenic acid
Antagonists:Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted:Ergolines (e.g.,metergoline,methysergide) Piperazines (e.g.,naphthylpiperazine)

5-HT₆

Agonists:Ergolines (e.g.,dihydroergocryptine,dihydroergotamine,ergotamine,lisuride,LSD,mesulergine,metergoline,methysergide) Hypidone Serotonin (5-HT) Tryptamines (e.g.,2-Me-5-HT,5-BT,5-CT,5-MT,Bufotenin,E-6801,E-6837,EMD-386088,EMDT,LY-586713,N-Me-5-HT,ST-1936,tryptamine) WAY-181187 WAY-208466
Antagonists:ABT-354 Atypical antipsychotics (e.g.,aripiprazole,asenapine,clorotepine,clozapine,fluperlapine,iloperidone,olanzapine,tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g.,amoxapine,mianserin) Tricyclic antidepressants (e.g.,amitriptyline,clomipramine,doxepin,nortriptyline) Typical antipsychotics (e.g.,chlorpromazine,loxapine)
Unknown/unsorted:Ergolines (e.g.,2-Br-LSD (BOL-148),bromocriptine,lergotrile,pergolide) Piperazines (e.g.,naphthylpiperazine)

5-HT₇

Agonists:8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g.,LSD) LP-12 LP-44 LP-211 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g.,frovatriptan) Tryptamines (e.g.,5-CT,5-MT,bufotenin,N-Me-5-HT)
Antagonists:Atypical antipsychotics (e.g.,amisulpride,aripiprazole,asenapine,brexpiprazole,clorotepine,clozapine,fluperlapine,olanzapine,risperidone,sertindole,tiospirone,ziprasidone,zotepine) Butaclamol DR-4485 EGIS-12233 Ergolines (e.g.,2-Br-LSD (BOL-148),amesergide,bromocriptine,cabergoline,dihydroergotamine,ergotamine,LY-53857,LY-215840,mesulergine,metergoline,methysergide,sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g.,amoxapine,maprotiline,mianserin,mirtazapine) Tricyclic antidepressants (e.g.,amitriptyline,clomipramine,imipramine) Typical antipsychotics (e.g.,acetophenazine,chlorpromazine,chlorprothixene,fluphenazine,loxapine,pimozide) Vortioxetine
Negative allosteric modulators:Oleamide
Unknown/unsorted:Ergolines (e.g.,lisuride,pergolide) Piperazines (e.g.,naphthylpiperazine)

See also:Receptor/signaling modulators
Adrenergics
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors andreleasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

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