A-84,543

A-84,543
Identifiers
IUPAC name
  • 3-{[(2S)-1-Methyl-2-pyrrolidinyl]methoxy}pyridine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H16N2O
Molar mass192.257 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCC[C@H]1COc2cccnc2
InChI
  • InChI=1S/C11H16N2O/c1-13-7-3-4-10(13)9-14-11-5-2-6-12-8-11/h2,5-6,8,10H,3-4,7,9H2,1H3/t10-/m0/s1 ☒N
  • Key:MVLJPWPLDPHKST-JTQLQIEISA-N ☒N
 ☒NcheckY (what is this?)  (verify)

A-84543 is a drug developed by Abbott, which acts as an agonist at neural nicotinic acetylcholine receptors with high selectivity for the α4β2 subtype. It is widely used in scientific research into the structure and function of this receptor subtype and has been the lead compound for the development of a large family of related derivatives.[1][2][3][4]

References

  1. ↑ Abreo MA, Lin NH, Garvey DS, Gunn DE, Hettinger AM, Wasicak JT, et al. (February 1996). "Novel 3-Pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors". Journal of Medicinal Chemistry. 39 (4): 817–25. doi:10.1021/jm9506884. PMID 8632405.
  2. ↑ Lin NH, Gunn DE, Li Y, He Y, Bai H, Ryther KB, et al. (February 1998). "Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist". Bioorganic & Medicinal Chemistry Letters. 8 (3): 249–54. doi:10.1016/S0960-894X(98)00019-5. PMID 9871663.
  3. ↑ Wei ZL, Xiao Y, Yuan H, Baydyuk M, Petukhov PA, Musachio JL, et al. (March 2005). "Novel pyridyl ring C5 substituted analogues of epibatidine and 3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine (A-84543) as highly selective agents for neuronal nicotinic acetylcholine receptors containing beta2 subunits". Journal of Medicinal Chemistry. 48 (6): 1721–4. doi:10.1021/jm0492406. PMID 15771418.
  4. ↑ Carreras J, Avenoza A, Busto JH, Peregrina JM (April 2007). "Synthesis of azabicyclo[2.2.n]alkane systems as analogues of 3-[1-methyl-2-(S)-pyrrolidinyl- methoxy]pyridine (A-84543)". The Journal of Organic Chemistry. 72 (8): 3112–5. doi:10.1021/jo0700732. PMID 17371077.
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