Mesembrine

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Basic information

CAS: 24880-43-1
Standard SMILES: COc1ccc([C@@]23CCC(=O)C[C@@H]2N(C)CC3)cc1OC
InChIKey: DAHIQPJTGIHDGO-IRXDYDNUSA-N
Molecular formula: C17H23NO3
Average molar mass: 289.4 g/mol
Monoisotopic mass: 289.1677936

Overview

Mesembrine is a member of pyrrolidines.

Names & identifiers

Preferred name: Mesembrine
IUPAC: (3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one
English name: Mesembrine
Molecular formula: C17H23NO3
Molecular weight: 289.36942

Names & synonyms

Mesembrine(-)-Mesembrine24880-43-1MesembranoneMesembrin(-)-MesembranoneMesembrine, (-)-4alpha,9alpha-Mesembrine86E2ZU4ETYDTXSID509477746H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aS,7aS)-6H-Indol-6-one, 3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3as-cis)-

Show more names

(3aS,7aS)-3a-(3,4-Dimethoxyphenyl)-1-methyloctahydro-6H-indol-6-one4α,9α-MeseMbrine( ) Mesembrine,()Mesembrine(7aβ)-1-Methyl-3aβ-(3,4-dimethoxyphenyl)octahydro-6H-indole-6-one(3aS,7aS)-3a-(3,4-DiMethoxyphenyl)octahydro-1-Methyl-6H-indol-6-one(3aS-cis)-3a-(3,4-DiMethoxyphenyl)octahydro-1- Methyl-6H-Indol-6-one

RefChem:8111393a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-oneDTXCID601376026P5X28MLQ1ZDL-MesembrineMesembrine [MI](+/-)-Mesembrine(+/-)-Mesembranone

Database identifiers

CAS: 24880-43-1、6023-73-0
PubChem CID: 394162
DTXSID: DTXSID50947774
ChEMBL: CHEMBL2008762
ChEBI: CHEBI:6778
UNII: 423182RCI5、86E2ZU4ETY
EC Number: 972-717-5
Nikkaji: J17.690G

Properties

Computed structural properties

XLogP: 2
Topological polar surface area: 38.8 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 21
Formal charge: 0
Complexity: 399

Physicochemical properties

alpha: 20 · D20 -55.4° (CH3OH)
Boiling point: 0.3 · bp0.3 186-190°
Density: 1.133 · 1.133±0.06 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: 10 mg/ml,Ethanol: · Chloroform: 10 mg/ml,Ethanol: 10 mg/ml
pka: 8.78 · 8.78±0.40(Predicted)
form: Oil to Solid
color: Colourless to Light Yellow
FDA UNII: 86 E2ZU4ETY · 86E2ZU4ETY
Symbol(GHS): 7 · GHS07
Signal word: Warning

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

Signal word: Warning
Symbol(GHS): GHS07

Chemistry & industry

Applications

UsesMesembrine is an alkaloid used in preparing Channa, a drug of Southwest Africa. A serotonin-uptake inhibitor; occurs naturally as the (-)-form.

Additional notes

DefinitionChEBI: Mesembrine is a member of pyrrolidines.

Related reactions

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Compound notes

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