Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H20N2O2.2ClH |
| Molecular Weight | 333.253 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.Cl.OCCCCC#CC1=CC(OC[C@@H]2CCN2)=CN=C1
InChI
InChIKey=WRSKKJWUXISFFU-UTLKBRERSA-N
InChI=1S/C15H20N2O2.2ClH/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;2*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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| Sazetidine-A, a selective α4β2 nicotinic acetylcholine receptor ligand: effects on dizocilpine and scopolamine-induced attentional impairments in female Sprague-Dawley rats. | 2011 Jun |
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| Cholinergic receptor system as a target for treating alcohol abuse and dependence. | 2012 Aug |
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| Novel medication targets for the treatment of alcoholism: preclinical studies. | 2012 Aug |
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| Assessing the effects of chronic sazetidine-A delivery on nicotine self-administration in both male and female rats. | 2012 Jul |
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| A new radioligand binding assay to measure the concentration of drugs in rodent brain ex vivo. | 2012 Nov |
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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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| Acute activation, desensitization and smoldering activation of human acetylcholine receptors. | 2013 |
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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 chronic sazetidine-A, a selective α4β2 neuronal nicotinic acetylcholine receptors desensitizing agent on pharmacologically-induced impaired attention in rats. | 2013 Mar |
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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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| Selective ligand behaviors provide new insights into agonist activation of nicotinic acetylcholine receptors. | 2014 May 16 |
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| Decreasing nicotinic receptor activity and the spatial learning impairment caused by the NMDA glutamate antagonist dizocilpine in rats. | 2014 Oct 15 |
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| Pharmacologically distinct nicotinic acetylcholine receptors drive efferent-mediated excitation in calyx-bearing vestibular afferents. | 2015 Feb 25 |
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| Evidence for the role of β2* nAChR desensitization in regulating body weight in obese mice. | 2016 Nov |
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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2455450-63-0
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56972183
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38SPN92UCW
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admin on Sat Dec 16 19:27:33 GMT 2023 , Edited by admin on Sat Dec 16 19:27:33 GMT 2023
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
