A-349821

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.

A-349821
Identifiers
IUPAC name
  • [4-[4-[3-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]propoxy]phenyl]phenyl]-morpholin-4-ylmethanone
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H34N2O3
Molar mass422.558 g·mol−1
3D model (JSmol)
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 Y
  • Key:CFUHKRLMDNFZED-NHCUHLMSSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. 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.
  2. 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.
  3. 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.2004.05.048. PMID 15294456.
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