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Isocorynoxeine

Names

[ CAS No. ]:
51014-29-0

[ Name ]:
Isocorynoxeine

[Synonym ]:
Methyl (16E,20α)-16-(methoxymethylene)-2-oxocorynox-18-en-17-oate
Y0112
17-methoxy-2-oxo-corynoxa-16,18-diene-16-carboxylic acid methyl ester
Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid, 6'-ethenyl-1,2,2',3',6',7',8',8'a-octahydro-α-(methoxymethylene)-2-oxo-, methyl ester, (αE,3S,6'R,7'S,8'aS)-
Isocorynoxeine
cisocorynoxeine

Biological Activity

[Description]:

Isocorynoxeine, an isorhynchophylline-related alkaloid, exhibits a dose-dependent inhibition of 5-HT2A receptor-mediated current response with an IC50 of 72.4 μM.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor
Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Natural Products >> Alkaloid
Research Areas >> Neurological Disease

[Target]

5-HT2A Receptor:72.4 μM (IC50)


[In Vitro]

Isocorynoxeine inhibits 5-HT2A receptor-mediated 5-HT currents. Isocorynoxeine prefer to interact with 5-HT2A receptors rather than with 5-HT2C receptors in the brain.Isocorynoxeine exhibits less potent inhibitory activity (with IC50 values of > 100 μM) against the 5-HT2C receptor-mediated response than the 5-HT2A receptor-mediated response in oocytes. Isocorynoxeine dose-dependently and competitively inhibits 5-HT-evoked currents in Xenopus oocytes expressing 5-HT2A receptors, but has less of a suppressive effect on those in oocytes expressing 5-HT2C receptors[1].

[In Vivo]

The effects of Rhynchophylline, Corynoxeine, and Isocorynoxeine, isorhynchophylline-related alkaloids present are tested in Uncaria species, on 5-MeO-DMT-induced head-twitch behaviour in reserpinized mice. Neither Rhynchophylline [H=1.369, P=0.504] nor Corynoxeine [H=0.242, P=0.886] affects the behaviour, while Isocorynoxeine significantly attenuates it at 30 mg/kg (i.p.) [H=7.582, P<0.01][1].

[Animal admin]

Mice[1] Male ICR mice are pretreated with Reserpine (5 mg/kg, i.p.) 3 h before the start of the experiments. Rhynchophylline (RHY), Corynoxeine (COX), Isocorynoxeine (ICOX, 10 and 30 mg/kg) or vehicle is injected i.p. 30 min before 5-MeO-DMT[1].

[References]

[1]. Matsumoto K, et al. Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies. Eur J Pharmacol. 2005 Jul 11;517(3):191-9.


[Related Small Molecules]

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Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
562.7±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C22H26N2O4

[ Molecular Weight ]:
382.453

[ Flash Point ]:
294.1±30.1 °C

[ Exact Mass ]:
382.189270

[ PSA ]:
71.36000

[ LogP ]:
3.07

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.606

[ Storage condition ]:
-20°C

Related Compounds