OUP-16

OUP-16
Names

IUPAC name 1-cyano-3-[[(2R,5R)-5-(1H-imidazol-5-yl)oxolan-2-yl]methyl]-2-methylguanidine
Identifiers
CAS Number	1038917-11-1 ^☒N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL321860 ^checkY
ChemSpider	24817698 ^checkY
PubChem CID	10106063
InChI InChI=1S/C11H16N6O/c1-13-11(16-6-12)15-4-8-2-3-10(18-8)9-5-14-7-17-9/h5,7-8,10H,2-4H2,1H3,(H,14,17)(H2,13,15,16)/t8-,10-/m1/s1 Key: CCOQWVUQXNRKKP-PSASIEDQSA-N
SMILES CN=C(NC[C@H]1CC[C@@H](O1)C2=CN=CN2)NC#N
Properties
Chemical formula	C₁₁H₁₆N₆O
Molar mass	248.290 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N (what is ^checkY☒N ?) Infobox references

Chemical compound

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OUP-16 is a histamine agonist selective for the H₄ subtype.^[1]

References

[edit ]

^ Hashimoto, T; Harusawa, S; Araki, L; Zuiderveld, OP; Smit, MJ; Imazu, T; Takashima, S; Yamamoto, Y; Sakamoto, Y; Kurihara, T; Leurs, R; Bakker, RA; Yamatodani, A (July 2003). "A Selective Human H₄-Receptor Agonist: (−)-2-Cyano-1-methyl-3-{(2R,5R)-5- [1H-imidazol-4(5)-yl]tetrahydrofuran-2-yl}methylguanidine". Journal of Medicinal Chemistry. 46 (14): 3162–5. doi:10.1021/jm0300025. PMID 12825954.

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Histamine receptor modulators

H₁

Agonists

Antagonists

Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, brilaroxazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine)
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)

H₂

Agonists	Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49
Antagonists	Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

H₃

Agonists	α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L-Histidine Methimepip Proxyfan
Antagonists	A-349821 A-423579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄

Agonists	4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430
Antagonists	JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002

See also: Receptor/signaling modulators; Monoamine metabolism modulators; Monoamine reuptake inhibitors

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