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Nuciferine 475-83-2 Lotus Leaf Extract
Nuciferine
CAS: 475-83-2
Molecular Formula: C19H21NO2
Name | Nuciferine |
Synonyms | 6a Nuciferin Nuciferine (-)-nucipherine (r)-1,2-dimethoxyaporphine Lotus Leaf Extract Nuciferin satis indigotica fort Extract 1,2-dimethoxy-6a-beta-aporphin 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (6aR)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline 4H-Dibenzo[de,g]quinoline,5,6,6a,7-tetrahydro-1,2-diMethoxy-6-Methyl-, (6aR)- Nuciferine 1,2-Dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline |
CAS | 475-83-2 |
InChI | InChI=1/C19H21NO2/c1-20-9-8-13-11-16(21-2)19(22-3)18-14-7-5-4-6-12(14)10-15(20)17(13)18/h4-7,11,15H,8-10H2,1-3H3 |
Molecular Formula | C19H21NO2 |
Molar Mass | 295.38 |
Density | 1.1156 (rough estimate) |
Melting Point | 165.5°C |
Boling Point | 437.06°C (rough estimate) |
Specific Rotation(α) | (c, 1 in EtOH)-164 |
Flash Point | 151.9°C |
Solubility | Easily soluble in low-polarity organic solvents such as benzene, ether, chloroform, haloalkanes, etc., and have better solubility in hydrophilic organic solvents such as acetone and ethanol, but less soluble or almost insoluble in water |
Vapor Presure | 1.27E-07mmHg at 25°C |
Appearance | White powder |
Color | white to beige |
pKa | 7.87±0.20(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.5000 (estimate) |
MDL | MFCD01664592 |
Physical and Chemical Properties | Soluble in benzene, ether, chloroform, halogenated alkanes and other organic solvents with low polarity, in acetone, ethanol and other hydrophilic organic solvents also have better solubility, the solubility in water is small or almost insoluble from the dried leaves of the Lotus |
In vitro study | Nuciferine is a partial agonist at DD 2 receptor with an activity (E max =67% of dopamine) similar to aripiprazole (E max =50% of dopamine). In line with its partial agonist activity, Nuciferine inhibited dopamine-induced activation of G i with a potency similar to clozapine (Nuciferine K B =62 nM; Clozapine K B =20 nM) as determined via Schild regression analysis. The natural product Nuciferine acts as an effective inhibitor of adult worm motility. Nuciferine is effective at inhibiting both basal and 5-HT evoked motility of adult schistosomes. Nuciferine inhibits Sm.5HTR L and schistosomule with 0.24±0.04 and 0.62±0.22 μM, respectively. |
In vivo study | In rodent models relevant to antipsychotic drug action, Nuciferine blocks head-twitch responses and discriminative stimulus effects of a 5-HT 2A agonist, substituted for clozapine discriminative stimulus, enhanced amphetamine induced locomotor activity, inhibited phencyclidine (PCP)-induced locomotor activity, and rescued PCP-induced disruption of prepulse inhibition without induction of catalepsy. In the presence of 1 or 3 mg/kg Nuciferine, cumulative PCP doses produce similar substitution to PCP alone. In the clozapine-trained animals, a dose-dependent substitution for 1.25 mg/kg clozapine is seen at 10 mg/kg Nuciferine (80.63% drug lever responding), with an ED 50 value of 5.42 mg/kg (95% CI 3.09-9.48 mg/kg) while the lower doses tested (0.1 mg/kg-3 mg/kg) fails to produce substitution for clozapine’s discriminative cue. In addition to a high percentage of responding on the clozapine-appropriate lever, 10 mg/kg Nuciferine also produces significant rate suppression as compared to vehicle control points (p<0.001). |
Plant source: | Lotus leaf |
alkaloid | nuciferine is an aporphine alkaloid extracted from the dried leaves of the Nymphaeaceae plant lotus. It is the main lipid-lowering active ingredient in lotus leaves. It is extracted from dried and crushed lotus leaves by a series of methods such as cellulase pretreatment, dilute hydrochloric acid extraction, ultrasonic-assisted extraction, and chloroform extraction. Traditional Chinese medicine believes that the lotus leaf is bitter and astringent in nature, flat, and belongs to the liver, spleen, stomach, and heart meridian. It has the effects of clearing heat and dampness, raising hair and clearing yang, cooling blood and stopping bleeding. The main chemical components of lotus leaves are nuciferine, citric acid, oxalic acid, etc. The main weight loss effect is nuciferine. Pharmacological studies have shown that lotus leaves have diuresis and laxative, intestinal toxicity, lipid-lowering and oil-removing, heat-clearing and antipyretic, etc. It can significantly reduce the content of triglyceride and cholesterol in serum, and has the health effect of regulating blood lipids. The use of lotus leaves to lose weight does not require deliberate dieting and has no side effects on the human body. |
Biological activity | Nuciferine is a 5-HT2A,5-HT2C and 5-HT2B antagonist, IC50 is 478 nM,131 nM and 1 μM respectively; It is also an inverse agonist of 5-HT7, IC50 is 150 nM. |
use | for content determination/identification/pharmacological experiments and other pharmacological effects: it has the effect of reducing weight and lipid. Clear heat and relieve heat, raise the hair and clear yang, cool the blood and stop bleeding |
CAS:
475-83-2
MF:
C19H21NO2
MW:
295.38
EINECS:
618-170-5
MDL No.:
MFCD01664592
Melting point:
165.5°C
Boiling point:
437.06°C (rough estimate)
Density
1.1156 (rough estimate)
refractive index
1.5000 (estimate)
storage temp.
2-8°C
solubility
DMSO : 11.11 mg/mL (37.61 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
form
powder
pka
7.87±0.20(Predicted)
color
white to beige
optical activity
[α]/D -145 to -165°, c = 0.5 in ethanol
LogP
2.357 (est)
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