3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one

Names

[ CAS No. ]:
468-53-1

[ Name ]:
3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one

[Synonym ]:
mesembrine

Biological Activity

[Description]:

Mesembrine ((+)-Mesembrine) a main alkaloid that features an aryloctahydroindole skeleton. Mesembrine is a 5-HT transporter inhibitor with a Ki of 1.4 nM. Mesembrine also inhibits phosphodiesterase 4B (PDE4B) with an IC50 of 7.8 μM[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

PDE4B:7.8 μM (IC50)

serotonin:1.4 nM (Ki)

[In Vitro]

Mesembrine can bind to cloned human cannabinoid CB1 receptors in vitro[1].

[References]

[1]. John L Krstenansky. Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacology. J Ethnopharmacol. 2017 Jan 4;195:10-19.

[2]. Golo M J Meyer, et al. GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high "Kanna" isolated from Sceletium tortuosum. Anal Bioanal Chem. 2015 Jan;407(3):761-78.

Chemical & Physical Properties

[ Molecular Formula ]:
C₁₇H₂₃NO₃

[ Molecular Weight ]:
289.36900

[ Exact Mass ]:
289.16800

[ PSA ]:
38.77000

[ LogP ]:
2.33660

[ Vapour Pressure ]:
3.09E-07mmHg at 25°C

Safety Information

[ Hazard Codes ]:
Xi