Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H20N2O2.ClH |
| Molecular Weight | 296.792 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.OCCCCC#CC1=CC(OC[C@@H]2CCN2)=CN=C1
InChI
InChIKey=KWQOEGGWZHGKHO-UQKRIMTDSA-N
InChI=1S/C15H20N2O2.ClH/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;1H/t14-;/m0./s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16857741 | https://www.ncbi.nlm.nih.gov/pubmed/18367540Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27444741 | https://www.ncbi.nlm.nih.gov/pubmed/22297831 | https://www.ncbi.nlm.nih.gov/pubmed/20535453 | https://www.ncbi.nlm.nih.gov/pubmed/18719450 | https://www.ncbi.nlm.nih.gov/pubmed/20435920 | https://www.ncbi.nlm.nih.gov/pubmed/24422997
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16857741 | https://www.ncbi.nlm.nih.gov/pubmed/18367540
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/27444741 | https://www.ncbi.nlm.nih.gov/pubmed/22297831 | https://www.ncbi.nlm.nih.gov/pubmed/20535453 | https://www.ncbi.nlm.nih.gov/pubmed/18719450 | https://www.ncbi.nlm.nih.gov/pubmed/20435920 | https://www.ncbi.nlm.nih.gov/pubmed/24422997
Sazetidine-A (6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol or AMOP-H-OH) is a "silent desensitizer" of neuronal nicotinic acetylcholine receptors (nAChRs), meaning that it desensitizes the receptor without first activating it. Later it was shown that Sazetidine-A is an agonist of native and recombinant alpha4beta2 nAChRs but shows differential efficacy on alpha4beta2 nAChRs subtypes. In animal models it is able to regulate the gain in body weight, alcohol and nicotine dependence. Sazetidine-A exerts analgesic, antidepressant and anxiolytic properties.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 0.64 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them. | 2006 Oct |
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| Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors. | 2008 Jun |
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| Nicotinic partial agonists varenicline and sazetidine-A have differential effects on affective behavior. | 2010 Aug |
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| Effects of sazetidine-A, a selective alpha4beta2 nicotinic acetylcholine receptor desensitizing agent on alcohol and nicotine self-administration in selectively bred alcohol-preferring (P) rats. | 2010 Aug |
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| The high-affinity nAChR partial agonists varenicline and sazetidine-A exhibit reinforcing properties in rats. | 2010 Dec 1 |
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| Chemistry and pharmacological characterization of novel nitrogen analogues of AMOP-H-OH (Sazetidine-A, 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol) as α4β2-nicotinic acetylcholine receptor-selective partial agonists. | 2010 Oct 14 |
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| Dissociation between duration of action in the forced swim test in mice and nicotinic acetylcholine receptor occupancy with sazetidine, varenicline, and 5-I-A85380. | 2011 Sep |
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| Chronic sazetidine-A at behaviorally active doses does not increase nicotinic cholinergic receptors in rodent brain. | 2012 Nov |
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| Chemistry and pharmacological studies of 3-alkoxy-2,5-disubstituted-pyridinyl compounds as novel selective α4β2 nicotinic acetylcholine receptor ligands that reduce alcohol intake in rats. | 2013 Apr 11 |
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| Effects of the sazetidine-a family of compounds on the body temperature in wildtype, nicotinic receptor β2-/- and α7-/- mice. | 2013 Oct 15 |
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| Divergent functional effects of sazetidine-a and varenicline during nicotine withdrawal. | 2013 Sep |
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| Nicotinic receptor modulation to treat alcohol and drug dependence. | 2014 |
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| The unique α4+/-α4 agonist binding site in (α4)3(β2)2 subtype nicotinic acetylcholine receptors permits differential agonist desensitization pharmacology versus the (α4)2(β2)3 subtype. | 2014 Jan |
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| Synthesis and pharmacological characterization of new neuronal nicotinic acetylcholine receptor ligands derived from Sazetidine-A. | 2014 Jul 1 |
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| Selective ligand behaviors provide new insights into agonist activation of nicotinic acetylcholine receptors. | 2014 May 16 |
Sample Use Guides
In the absence of PNU-120596, sazetidine-A elicited mecamylamine-sensitive increases in fluorescence in SH-SY5Y cells (EC50 4.2 µM) but no responses from primary cortical neurons. In the presence on PNU-120596, an additional response to sazetidine-A was observed in SH-SY5Y cells (EC50 0.4 µM) and robust responses were recorded in 14 % of cortical neurons.
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77108155
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1197329-42-2
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YUU6E4XT44
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DTXSID701010180
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admin on Sat Dec 16 19:33:01 GMT 2023 , Edited by admin on Sat Dec 16 19:33:01 GMT 2023
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
