| Identification | Back Directory | [Name]
Mahanimbine | [CAS]
21104-28-9 | [Synonyms]
Mahanimbin
Mahanimbine
(+)-3,11-Dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)pyrano[3,2-a]carbazole
Pyrano[3,2-a]carbazole, 3,11-dihydro-3,5-dimethyl-3-(4-methyl-3-penten-1-yl)-, (3S)- | [Molecular Formula]
C23H25NO | [MDL Number]
MFCD20731071 | [MOL File]
21104-28-9.mol | [Molecular Weight]
331.45 |
| Chemical Properties | Back Directory | [Melting point ]
94-95 °C | [Boiling point ]
502.6±39.0 °C(Predicted) | [density ]
1.109 | [solubility ]
DMSO: 10 mM | [form ]
neat | [pka]
17.31±0.40(Predicted) | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C23H25NO/c1-15(2)8-7-12-23(4)13-11-18-21-19(14-16(3)22(18)25-23)17-9-5-6-10-20(17)24-21/h5-6,8-11,13-14,24H,7,12H2,1-4H3/t23-/m0/s1 | [InChIKey]
HTNVFUBCWIYPJN-QHCPKHFHSA-N | [SMILES]
N1C2=C(C=CC=C2)C2=C1C1C=C[C@](C)(CC/C=C(\C)/C)OC=1C(C)=C2 |
| Hazard Information | Back Directory | [Description]
The leaves of Murraya koenigii Spreng. also furnish this crystalline alkaloid
which is dextrorotatory with [α]D + 52° (CHCI3). The ultraviolet spectrum
exhibits several absorption maxima occurring at 227, 288,300,315,328,343
and 357 mil. It furnishes a crystalline picrate as pale yellow needles, m.p. 142°C
and on catalytic reduction gives the dihydro derivative, m.p. 101°C and finally
the tetrahydro compound, m.p. 108°C. Spectroscopic and chemical data support
the structure given above. | [Uses]
Mahanimbine is an orally active alkaloid from Murraya koenigii. Mahanimbine inhibits progression of high-fat diet (HFD)-induced metabolic complications in mice[1]. | [Definition]
ChEBI: Mahanimbine is a member of carbazoles. | [in vivo]
Mahanimbine (2-4 mg/kg; p.o.; daily for 12 weeks) prevents HFD-induced weight gain in mice (male and female)[1].
Mahanimbine prevented HFD-induced hyperlipidemia and fat accumulation in adipose tissue and liver along with the restricted progression of systemic inflammation and oxidative stress[1].
Mahanimbine treatment improves glucose clearance and upregulates the expression of insulin responsive genes in liver and adipose tissue[1]. | Animal Model: | Swiss albino mice (7-8 weeks old, both sex)[1] | | Dosage: | HFD+LD (2 mg/kg of body weight of mahanimbine), HFD+HD (4 mg/kg of body weight of mahanimbine); | | Administration: | Oral suspension; daily for 12 weeks | | Result: | Male HFD+LD and HFD+HD groups showed 51.70±6 3.59% and 47.37±3.73% weight gain, respectively, as compared with 71.02±6 6.04% in HFD fed mice whereas female HFD+LD and HFD+HD groups showed 24.31±1.68% and 25.10±2.61% weight gain as compared with HFD group with 36.69±3.60% of weight gain.
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| [References]
Chakraborty, Das, Bose., Sci. Cult. (Calcutta), 32, 83 (1966)
Structure:
Narasimhan, Paradkar, Chitguppi., Tetrahedron Lett., 5501 (1968) |
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