MRS8209

Pharmaceutical compound

MRS8209
Identifiers

IUPAC name 4-[6-(cyclopentylamino)-2-iodopurin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carbonitrile
Chemical and physical data
Formula	C₁₇H₁₉IN₆O₂
Molar mass	466.283g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O[C@H]1[C@@H](O)[C@@H]([C@H]2C[C@]21C#N)n1cnc2c1nc(I)nc2NC1CCCC1

MRS8209 is an experimental drug which acts as a potent, peripherally selective 5-HT_2B receptor antagonist with high selectivity over other serotonin receptor subtypes. It has been investigated for possible applications in the treatment of heart and lung fibrosis and intestinal or vascular conditions mediated by 5-HT_2B, while sparing 5-HT_2B mediated activity in the brain.^[1]

References

[edit ]

↑ Tosh DK, Pavan M, Clark AA, Lammers J, Villano S, Marri S, et al. (December 2024). "Potent and Selective Human 5-HT2B Serotonin Receptor Antagonists: 4'-Cyano-(N)-methanocarba-adenosines by Synthetic Serendipity". Journal of Medicinal Chemistry. 67 (23): 21264–21291. doi:10.1021/acs.jmedchem.4c02174. PMC 11715225 . PMID 39589936.

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Serotonin receptor modulators

5-HT₁

5-HT_1A	Agonists: Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) AP-521 Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, elopiprazole, lurasidone, perospirone, quetiapine, tiospirone, umespirone, ziprasidone) Azapirones (e.g., alnespirone, binospirone, BMY-7378, buspirone, enilospirone, eptapirone (F-11440), gepirone, ipsapirone, perospirone, revospirone, tandospirone, tiospirone, umespirone, zalospirone) Befiradol (NLX-112; F-13640) Bifeprunox BMY-14802 (BMS-181100) Cannabidiol Dimemebfe Dopamine DSP-0038 DSP-1181 Ebalzotan Eltoprazine Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-8910-RS F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 (NLX-101) F-17464 FKW00GA (TGW00AA) Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-315712 mCPP Naftopidil Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) Oxaflozane Pardoprunox Partial ergolines (e.g., 6-MeO-RU-28306, 8-OH-DPAT, LY-178210 (LY-228729), Bay R 1531 (LY-197206), FHATHBIN, LY-293284, LY-301317, RU-28306, U-92016A (U92016A)) Piclozotan Piromelatine Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SKL-PSY (FZ-016) SSR-181507 SUN-8399 Sunepitron Tryptamines (e.g., 4-F-5-MeO-pyr-T, 5-CT, 5-MeO-DMT, 5-MeO-pip-T, 5-MeO-pyr-T, 5-MT, bufotenin, DMT, GR-46611, indorenate, N-Me-5-HT, psilocin, psilocybin) TGBA01AD (FKB01MD) TGFK-09SD (TGFK09SD) TMU4142 TZB-30878 Ulotaront Urapidil VML-670 (CEB-1555) Xaliproden Yohimbine Positive allosteric modulators: Cannabicyclol (CBL) Oleamide Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione GSK-958108 Lecozotan LY-206130 LY-297996 ((–)-LY206130) LY-426965 Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-272183 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 ((S)-5-FHDPAT) WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Acetryptine Carvedilol Ergolines (e.g., ergometrine (ergonovine))
5-HT_1B	Agonists: (S)-DCPT Alniditan 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-12066 (CGS-12066A, CGS-12066B) CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) GR-46611 mCPP Methylenedioxyphenethylamines (e.g., MDMA, methylone) PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, IS-159, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine Antagonists: AOP-208 (LB-208) AR-A000002 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 SB-272183 SB-616234 Trelanserin Yohimbine Negative allosteric modulators: 5-HT-moduline Miscellaneous: HG1 (5-HT-moduline antagonist) Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)
5-HT_1D	Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) CP-122288 CP-135807 CP-286601 Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) GR-46611 L-694247 L-772405 mCPP Piromelatine PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD (FKB01MD) Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, IS-159, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) Antagonists: BRL-15572 Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin SB-272183 Yohimbine Ziprasidone Negative allosteric modulators: 5-HT-moduline 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 Unknown/unsorted: LY-53857 LY-86057

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, BMB-202) 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 Aporphines and noraporphines (e.g., (S)-glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine) BMB-201 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 IHCH-8110 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, VCU-1012) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) UH-232 Positive allosteric modulators: AB0124 CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide Antagonists: 4F-4PP 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) Barettin Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane DLX-2270 Dotarizine DSP-0038 DSP-6745 Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin FCE-24379 FKW00GA (TGW00AA) Flibanserin Glemanserin Irindalone KB-128 Ketanserin KML-010 Landipirdine LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin R-96544 R-102444 Rauwolscine Ritanserin Roluperidone S-14671 SpAMDA Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) Temanogrel Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TGBA01AD (FKB01MD) Trelanserin 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: 1-Methylmedmain 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) IHCH-8110 KB-128 Ketanserin LY-393558 mCPP Medmain Metadoxine Metitepine (methiothepin) Minaprine MRS8209 MW073 Pirenperone Piromelatine 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 Aporphines and noraporphines (e.g., MQ02-439, (S)-glaucine, nornuciferine, asimilobine, 11-chloroasimilobine, 11-methoxyasimilobine) ATHX-105 Bexicaserin BMB-101 BMB-105 BMB-201 Centhaquine CP-809101 Dimemebfe DLX-2270 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 IHCH-8110 KB-128 Lorcaserin Lumocaserin LY03020 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 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine, CPI-CG-8) Vabicaserin VR-1065 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 DSP-6745 Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin 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 Itasetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g., loxapine) TZB-30878 Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) Vortioxetine Zacopride Zatosetron Negative allosteric modulators: Bupropion Colchicine Hydroxybupropion Unknown/unsorted: 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 DSP-6745 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 and releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

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