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

Modify Date: 2024-01-04 18:43:30

3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one Structure
3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one structure
Common Name 3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one
CAS Number 468-53-1 Molecular Weight 289.36900
Density N/A Boiling Point N/A
Molecular Formula C17H23NO3 Melting Point N/A
MSDS N/A Flash Point N/A

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


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].

 Names

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

  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
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

 Synonyms

mesembrine
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