:Sazetidine A

{{Short description|Pharmaceutical drug}}

{{Drugbox

| verifiedrevid = 451222236

| IUPAC_name = 6-[5-[(2S)-2-Azetidinylmethoxy]-3-pyridinyl]-5-hexyn-1-ol

| image = Sazetidine A.svg

| width = 240

| tradename =

| routes_of_administration =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 820231-95-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = LH23S35NSM

| ATC_suffix =

| PubChem = 11983356

| DrugBank =

| ChemSpiderID = 10155861

| C=15 | H=20 | N=2 | O=2

| smiles = OCCCCC#Cc1cc(cnc1)OCC2CCN2

| StdInChI = 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

| StdInChIKey = WONBUILDJNKYCB-AWEZNQCLSA-N

}}

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.{{cite journal | vauthors = Xiao Y, Fan H, Musachio JL, Wei ZL, Chellappan SK, Kozikowski AP, Kellar KJ | title = Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them | journal = Molecular Pharmacology | volume = 70 | issue = 4 | pages = 1454–60 | date = October 2006 | pmid = 16857741 | doi = 10.1124/mol.106.027318 | s2cid = 6599272 }}{{cite journal | vauthors = Zwart R, Carbone AL, Moroni M, Bermudez I, Mogg AJ, Folly EA, Broad LM, Williams AC, Zhang D, Ding C, Heinz BA, Sher E | display-authors = 6 | title = Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors | journal = Molecular Pharmacology | volume = 73 | issue = 6 | pages = 1838–43 | date = June 2008 | pmid = 18367540 | doi = 10.1124/mol.108.045104 | s2cid = 24632914 }} It has potent analgesic effects in animal studies comparable to those of epibatidine, but with less toxicity,{{cite journal | vauthors = Cucchiaro G, Xiao Y, Gonzalez-Sulser A, Kellar KJ | title = Analgesic effects of Sazetidine-A, a new nicotinic cholinergic drug | journal = Anesthesiology | volume = 109 | issue = 3 | pages = 512–9 | date = September 2008 | pmid = 18719450 | doi = 10.1097/ALN.0b013e3181834490 | s2cid = 22185882 | doi-access = free }} and also has antidepressant action.{{cite journal | vauthors = Kozikowski AP, Eaton JB, Bajjuri KM, Chellappan SK, Chen Y, Karadi S, He R, Caldarone B, Manzano M, Yuen PW, Lukas RJ | display-authors = 6 | title = 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 | journal = ChemMedChem | volume = 4 | issue = 8 | pages = 1279–91 | date = August 2009 | pmid = 19569163 | pmc = 2955514 | doi = 10.1002/cmdc.200900079 }}