A-349821

Chemical compound

Pharmaceutical compound

A-349821
Identifiers

IUPAC name [4-[4-[3-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]propoxy]phenyl]phenyl]-morpholin-4-ylmethanone
CAS Number	372513-99-0 ^☒N 556835-30-4 (trifluoroacetate salt)
PubChem CID	9954017
IUPHAR/BPS	1217
ChemSpider	8129627 ^checkY
UNII	67WL275ISI
ChEMBL	ChEMBL179702 ^checkY
CompTox Dashboard (EPA)	DTXSID701116601 Edit this at Wikidata
Chemical and physical data
Formula	C₂₆H₃₄N₂O₃
Molar mass	422.569 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H]1CC[C@H](N1CCCOC2=CC=C(C=C2)C3=CC=C(C=C3)C(=O)N4CCOCC4)C
InChI InChI=1S/C26H34N2O3/c1-20-4-5-21(2)28(20)14-3-17-31-25-12-10-23(11-13-25)22-6-8-24(9-7-22)26(29)27-15-18-30-19-16-27/h6-13,20-21H,3-5,14-19H2,1-2H3/t20-,21-/m1/s1^checkY Key:CFUHKRLMDNFZED-NHCUHLMSSA-N^checkY
^☒NcheckY (what is this?) (verify)

A-349,821 is a potent and selective histamine H₃ receptor antagonist ^[1] (or possibly an inverse agonist).^[2] It has nootropic effects in animal studies,^[3] although there do not appear to be any plans for clinical development at present and it is currently only used in laboratory research.^{[citation needed ]}

References

^ Faghih R, Dwight W, Pan JB, Fox GB, Krueger KM, Esbenshade TA, et al. (April 2003). "Synthesis and SAR of aminoalkoxy-biaryl-4-carboxamides: novel and selective histamine H3 receptor antagonists". Bioorganic & Medicinal Chemistry Letters. 13 (7): 1325–8. doi:10.1016/S0960-894X(03)00118-5. PMID 12657274.
^ Witte DG, Yao BB, Miller TR, Carr TL, Cassar S, Sharma R, et al. (July 2006). "Detection of multiple H3 receptor affinity states utilizing [3H]A-349821, a novel, selective, non-imidazole histamine H3 receptor inverse agonist radioligand". British Journal of Pharmacology. 148 (5): 657–70. doi:10.1038/sj.bjp.0706752. PMC 1751875 . PMID 16715122.
^ Esbenshade TA, Fox GB, Krueger KM, Baranowski JL, Miller TR, Kang CH, et al. (September 2004). "Pharmacological and behavioral properties of A-349821, a selective and potent human histamine H3 receptor antagonist". Biochemical Pharmacology. 68 (5): 933–45. doi:10.1016/j.bcp.2004年05月04日8. PMID 15294456.

H₁

Agonists

Antagonists

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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