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
| 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 |
| 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 |
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 |
|
| 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 |
|
| Cholinergic receptor system as a target for treating alcohol abuse and dependence. | 2012 Aug |
|
| 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 |
|
| Effects of chronic sazetidine-A, a selective α4β2 neuronal nicotinic acetylcholine receptors desensitizing agent on pharmacologically-induced impaired attention in rats. | 2013 Mar |
|
| Effects of the sazetidine-a family of compounds on the body temperature in wildtype, nicotinic receptor β2-/- and α7-/- mice. | 2013 Oct 15 |
|
| Nicotinic receptor modulation to treat alcohol and drug dependence. | 2014 |
|
| 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 |
|
| Synthesis and pharmacological characterization of new neuronal nicotinic acetylcholine receptor ligands derived from Sazetidine-A. | 2014 Jul 1 |
|
| 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 |
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 19:27:33 GMT 2023
by
admin
on
Sat Dec 16 19:27:33 GMT 2023
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| Record UNII |
38SPN92UCW
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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2455450-63-0
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56972183
Created by
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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38SPN92UCW
Created by
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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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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