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
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C15H20N2O2 |
| Molecular Weight | 260.3315 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|
| Sazetidine-A is a potent and selective agonist at native and recombinant alpha 4 beta 2 nicotinic acetylcholine receptors. | 2008 Jun |
|
| Nicotinic partial agonists varenicline and sazetidine-A have differential effects on affective behavior. | 2010 Aug |
|
| 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 |
|
| 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 |
|
| Sazetidine-A, a selective α4β2 nicotinic acetylcholine receptor ligand: effects on dizocilpine and scopolamine-induced attentional impairments in female Sprague-Dawley rats. | 2011 Jun |
|
| Discovery of isoxazole analogues of sazetidine-A as selective α4β2-nicotinic acetylcholine receptor partial agonists for the treatment of depression. | 2011 Oct 27 |
|
| 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 |
|
| Assessing the effects of chronic sazetidine-A delivery on nicotine self-administration in both male and female rats. | 2012 Jul |
|
| Effects of sazetidine-A, a selective α4β2* nicotinic receptor desensitizing agent, on body temperature regulation in mice and rats. | 2012 May 5 |
|
| Acute activation, desensitization and smoldering activation of human acetylcholine receptors. | 2013 |
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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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| Nicotinic receptor modulation to treat alcohol and drug dependence. | 2014 |
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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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| Chronic sazetidine-A maintains anxiolytic effects and slower weight gain following chronic nicotine without maintaining increased density of nicotinic receptors in rodent brain. | 2014 May |
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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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| Sazetidine-A Activates and Desensitizes Native α7 Nicotinic Acetylcholine Receptors. | 2015 Oct |
|
| Evidence for the role of β2* nAChR desensitization in regulating body weight in obese mice. | 2016 Nov |
|
| The effect of sazetidine-A and other nicotinic ligands on nicotine controlled goal-tracking in female and male rats. | 2017 Feb |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 19:33:01 GMT 2023
by
admin
on
Sat Dec 16 19:33:01 GMT 2023
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| Record UNII |
YUU6E4XT44
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID701010180
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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