ChemicalBook CAS DataBase List 21104-28-9

21104-28-9

Name	Mahanimbine
CAS	21104-28-9
Molecular Formula	C23H25NO
MDL Number	MFCD20731071
Molecular Weight	331.45
MOL File	21104-28-9.mol

Chemical Properties

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

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H319-H413
Precautionary statements	P264-P270-P273-P280-P301+P312-P305+P351+P338
Risk Statements	53 less more
WGK Germany	3

Hazard Information

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.

References

Chakraborty, Das, Bose., Sci. Cult. (Calcutta), 32, 83 (1966) Structure: Narasimhan, Paradkar, Chitguppi., Tetrahedron Lett., 5501 (1968)

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