Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H17N3 |
Molecular Weight | 227.3049 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC1)C2=NC3=CC=CC=C3C=C2
InChI
InChIKey=HOMWNUXPSJQSSU-UHFFFAOYSA-N
InChI=1S/C14H17N3/c1-16-8-10-17(11-9-16)14-7-6-12-4-2-3-5-13(12)15-14/h2-7H,8-11H2,1H3
N-Methylquipazine is a tertiary amine analog of quipazine. It binds at 5-HT3 sites with an affinity similar to that of quipazine. N-methylquipazine has a low affinity for 5-HT1A, 5-HT1B, 5-HT2, a1, a2 and muscarinic receptors. It produces a concentration-dependent increase in extracellular dopamine levels in the anterior medial prefrontal cortex. This action is dependent on the presence of Ca+2, is impulse-dependent, and depends on newly synthesized dopamine stores. The increase in the anterior medial prefrontal cortex dopamine levels by n-methylquipazine is probably, not mediated by its interaction with the 5-HT3 receptor. It might be an be an attractive candidate as a radioligand for the PET studies of 5-HT3 receptors in man.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9290075
Curator's Comment: Known to be CNS penetrant in rat and monkey. Human data not available.
Originator
Sources: https://patents.google.com/patent/US3737540/
Curator's Comment: # Bayer Corp.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094116 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2583244 |
4.7 nM [IC50] | ||
Target ID: CHEMBL2093870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2583244 |
550.0 nM [IC50] | ||
Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2583244 |
1.7 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Binding of arylpiperazines to 5-HT3 serotonin receptors: results of a structure-affinity study. | 1989 Sep 22 |
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The characterization of the effect of locally applied N-methylquipazine, a 5-HT3 receptor agonist, on extracellular dopamine levels in the anterior medial prefrontal cortex in the rat: an in vivo microdialysis study. | 1996 Dec |
|
Arylpiperazines with serotonin-3 antagonist activity: a comparative molecular field analysis. | 1998 Jun 4 |
|
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. | 2009 Oct 23 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10638822
Rat: 10-1000 uM
Route of Administration:
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5013
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0YV1ZIR6S0
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DTXSID8043731
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28614-26-8
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SALT/SOLVATE (PARENT)
SUBSTANCE RECORD