Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H20N2O2 |
| Molecular Weight | 260.3315 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OCCCCC#CC1=CC(OC[C@@H]2CCN2)=CN=C1
InChI
InChIKey=WONBUILDJNKYCB-AWEZNQCLSA-N
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
| 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 |
|---|---|---|
| Novel medication targets for the treatment of alcoholism: preclinical studies. | 2012 Aug |
|
| Chronic sazetidine-A at behaviorally active doses does not increase nicotinic cholinergic receptors in rodent brain. | 2012 Nov |
|
| 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 |
|
| 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 |
|
| Decreasing nicotinic receptor activity and the spatial learning impairment caused by the NMDA glutamate antagonist dizocilpine in rats. | 2014 Oct 15 |
|
| PKCε phosphorylates α4β2 nicotinic ACh receptors and promotes recovery from desensitization. | 2015 Sep |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:20:12 GMT 2023
by
admin
on
Sat Dec 16 15:20:12 GMT 2023
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| Record UNII |
LH23S35NSM
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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DTXSID401010179
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11983356
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820231-95-6
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LH23S35NSM
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Sazetidine A
Created by
admin on Sat Dec 16 15:20:12 GMT 2023 , Edited by admin on Sat Dec 16 15:20:12 GMT 2023
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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