Sazetidine A

Sazetidine A (AMOP-H-OH) is a drug which acts as a subtype selective partial agonist at α4β2 neural nicotinic acetylcholine receptors, acting as an agonist at (α4)2(β2)3 pentamers, but as an antagonist at (α4)3(β2)2 pentamers.[1][2] It has potent analgesic effects in animal studies comparable to those of epibatidine, but with less toxicity,[3] and also has antidepressant action.[4]

Sazetidine A
Identifiers
IUPAC name
  • 6-[5-[(2S)-2-Azetidinylmethoxy]-3-pyridinyl]-5-hexyn-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H20N2O2
Molar mass260.331 g·mol−1
3D model (JSmol)
SMILES
  • OCCCCC#Cc1cc(cnc1)OCC2CCN2
InChI
  • InChI=1S/C15H20N2O2/c18-8-4-2-1-3-5-13-9-15(11-16-10-13)19-12-14-6-7-17-14/h9-11,14,17-18H,1-2,4,6-8,12H2/t14-/m0/s1
  • Key:WONBUILDJNKYCB-AWEZNQCLSA-N
  (verify)

References
  1. Xiao Y, Fan H, Musachio JL, Wei ZL, Chellappan SK, Kozikowski AP, Kellar KJ (October 2006). "Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them". Molecular Pharmacology. 70 (4): 1454–60. doi:10.1124/mol.106.027318. PMID 16857741. S2CID 6599272.
  2. Zwart R, Carbone AL, Moroni M, Bermudez I, Mogg AJ, Folly EA, et al. (June 2008). "Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors". Molecular Pharmacology. 73 (6): 1838–43. doi:10.1124/mol.108.045104. PMID 18367540. S2CID 24632914.
  3. Cucchiaro G, Xiao Y, Gonzalez-Sulser A, Kellar KJ (September 2008). "Analgesic effects of Sazetidine-A, a new nicotinic cholinergic drug". Anesthesiology. 109 (3): 512–9. doi:10.1097/ALN.0b013e3181834490. PMID 18719450. S2CID 22185882.
  4. Kozikowski AP, Eaton JB, Bajjuri KM, Chellappan SK, Chen Y, Karadi S, et al. (August 2009). "Chemistry and pharmacology of nicotinic ligands based on 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol (AMOP-H-OH) for possible use in depression". ChemMedChem. 4 (8): 1279–91. doi:10.1002/cmdc.200900079. PMC 2955514. PMID 19569163.
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