Name: Mesembrine
SKU: 468-53-1

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Basic Information

Molecular Structure:
CAS No.:	468-53-1
Name:	Mesembrine
Article Data:	26

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide Ambient temperature;

: C19H27NO4

: 468-53-1
(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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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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

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Specification