A-349821

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 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.

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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