Stereochemistry | RACEMIC |
Molecular Formula | C22H31NO3.ClH |
Molecular Weight | 393.947 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 2 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1C[C@@H]2CCC[C@H](C1)[C@@H]2OC(=O)C(O)(C3CCCC3)C4=CC=CC=C4
InChI
InChIKey=AUKYHFFECJXLHI-UHFFFAOYSA-N
InChI=1S/C22H31NO3.ClH/c1-23-14-16-8-7-9-17(15-23)20(16)26-21(24)22(25,19-12-5-6-13-19)18-10-3-2-4-11-18;/h2-4,10-11,16-17,19-20,25H,5-9,12-15H2,1H3;1H
Phencynonate (PHH) is a novel anticholinergic compound. It is structurally similar to scopolamine, possesses both muscarinic and nicotinic antagonistic properties as well as anti-NMDA properties. It has been developed as a safe and effective drug for the prevention of motion sickness in tablet form, it also demonstrates clear anticonvulsant effectiveness after soman poisoning in a rat model. S-isomer was more effective against motion sickness and had not anxiogenic action at therapeutic doses. S-isomer has the higher affinity and activity for mAChR in cerebral cortex and acted as a competitive mAChR antagonist. PHH was able to suppress chronic unpredictable mild stress (CUMS)-induced oxidative stress and enhance the antioxidant capacity and antioxidant proteins activity, such as superoxide dismutase 2 (SOD2) and peroxiredoxin 6 (Prdx6). PHH ameliorated CUMS-induced depressive phenotypes by up-regulating SIRT6 deacetylation activity. PHH-mediating SIRT6 pathway is required for antidepressant response and PHH can be used as a novel therapeutic to effectively treat depression. Phencynonate is in phase III clinical trials for the treatment of vertigo.