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468-53-1

Basic Information
CAS No.: 468-53-1
Name: Mesembrine
Article Data: 26
Molecular Structure:
Molecular Structure of 468-53-1 (Mesembrine)
Formula: C17H23NO3
Molecular Weight: 289.375
Synonyms: 3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one;(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one;
Density: 1.133 g/cm3
Boiling Point: 419.2 °C at 760 mmHg
Flash Point: 207.3 °C
PSA: 38.77000
LogP: 2.33660
Synthetic route

t-butyl 2-((S)-1-(3,4-dimethoxyphenyl)-4-oxocyclohex-2-enyl)ethylmethylcarbamate

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1.33333h;81%

(R)-3a-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,3a,4,5-hexahydro-6H-indol-6-one

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With ammonium hydroxide; lithium In tetrahydrofuran; tert-butyl alcohol for 0.5h; Birch Reduction; Inert atmosphere;77%
With ammonia; lithium In tetrahydrofuran; tert-butyl alcohol at -78℃; for 0.75h;77%
911847-34-2

(3aR,8bS)-3a-(3,4-dimethoxyphenyl)-1,6-dimethyl-1,2,3,3a,4,5,6,8b-octahydro-8H-isoxazolo[3,4-g]indol-8-one

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile for 12h; Heating;75%
1427472-33-0

(3aR,6S,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With dipyridinium dichromate In dichloromethane at 20℃; for 2h; Inert atmosphere;48%
99548-21-7

(R)-2-(3,4-Dimethoxy-phenyl)-2-(2-methylamino-ethyl)-5-oxo-hexanal

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;

C19H27NO4

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
With acid Yield given;
911847-30-8

[(S)-1-(3,4-Dimethoxy-phenyl)-3-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-oxo-cyclohex-2-enyl]-acetaldehyde

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
2: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
3: 60 percent / ethanol / 6 h / Heating
4: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme

(S)-4-(3,4-Dimethoxy-phenyl)-2-((S)-2-methoxymethyl-pyrrolidine-1-carbonyl)-4-{2-[(E)-methylimino]-ethyl}-cyclohex-2-enone

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
2: 60 percent / ethanol / 6 h / Heating
3: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
911847-24-0

((R)-1-allyl-5-(3,4-dimethoxyphenyl)-2-methoxycyclohexa-2,5-dienyl)((S)-2-(methoxymethyl)pyrrolidin-1-yl)methanone

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 95 percent / HCl / methanol / 15 h / 20 °C
2.1: 80 percent / 1,2-dichloro-benzene / 10 h / Heating
3.1: O3; Sudan III / methanol / 0.03 h / -78 °C
3.2: dimethyl sulfide / methanol / 7 h / 20 °C
4.1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
5.1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
6.1: 60 percent / ethanol / 6 h / Heating
7.1: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
911847-28-4

(S)-4-allyl-4-(3,4-dimethoxyphenyl)-2-((S)-2-(methoxymethyl)pyrrolidin-1-carbonyl)cyclohex-2-en-1-one

468-53-1

(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: O3; Sudan III / methanol / 0.03 h / -78 °C
1.2: dimethyl sulfide / methanol / 7 h / 20 °C
2.1: triethylamine / 1,2-dichloro-ethane / 0.08 h / 20 °C
3.1: 190 mg / NaBH3CN / 1,2-dichloro-ethane / 6 h / 20 °C
4.1: 60 percent / ethanol / 6 h / Heating
5.1: 75 percent / Mo(CO)6 / acetonitrile; H2O / 12 h / Heating
View Scheme
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  • 6H-Indol-6-one,3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aR,7aR)-

  • Casno:

    468-53-1

    6H-Indol-6-one,3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aR,7aR)-

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  • 6H-Indol-6-one,3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-, (3aR,7aR)-

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  • Mesembrine cas  468-53-1

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Specification

The Mesembrine, with the CAS registry number 468-53-1, is also known as 3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one. The molecular formula of this chemical is C17H23NO3 and molecular weight is 289.3694. What's more, its IUPAC name is (3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one. In addition, it should be stored in condition of cold and dry. It has been shown to act as a serotonin reuptake inhibitor, and more recently, has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4).

Physical properties about Mesembrine are: (1)ACD/LogP: 1.952; (2)ACD/LogD (pH 5.5): -0.93; (3)ACD/LogD (pH 7.4): 0.56; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 11.21; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 3; (10)Index of Refraction: 1.548; (11)Molar Refractivity: 81.053 cm3; (12)Molar Volume: 255.188 cm3; (13)Polarizability: 32.132 10-24cm3; (14)Surface Tension: 41.6389999389648 dyne/cm; (15)Density: 1.134 g/cm3; (16)Flash Point: 207.329 °C; (17)Enthalpy of Vaporization: 67.287 kJ/mol; (18)Boiling Point: 419.206 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1) SMILES: O=C3CC[C@@]2(c1ccc(OC)c(OC)c1)[C@H](N(CC2)C)C3
(2) InChI: InChI=1/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1
(3) InChIKey: DAHIQPJTGIHDGO-IAGOWNOFBH