| Identification | Back Directory | [Name]
CONESSINE | [CAS]
546-06-5 | [Synonyms]
NERVINE
NERIINE
CONESSIN
Konessin
CONESSINE
WRIGHTINE
ROGUESSINE
ROQUESSINE
NSC 119994
Conessinum
CONESSINE(P)
CONESSINE(RG)
5-CONENIN-3BETA-DIMETHYLAMINE
N,N-Dimethyl-con-5-enin-3-amine
n,18-dihydrotrimethyl-conkurchin
Conessine (Wrightine Roguessine)
3-beta-(dimethylamino)-con-5-enin
3-beta-(dimethylamino)con-5-enine
(3β)-N,N-dimethyl-con-5-enin-3-amine
n-dimethyl-(3-beta)-con-5-enin-3-amin
Con-5-enin-3-amine,N,N-dimethyl-, (3b)-
Con-5-enin-3-amine, N,N-dimethyl-, (3β)-
(3-BETA)-N,N-DIMETHYL-CON-5-ENIN-3-AMINE | [EINECS(EC#)]
208-897-2 | [Molecular Formula]
C24H40N2 | [MDL Number]
MFCD00016752 | [MOL File]
546-06-5.mol | [Molecular Weight]
356.59 |
| Chemical Properties | Back Directory | [Melting point ]
126-127°C | [alpha ]
D20 +25.3° (c = 0.7 in abs alc) | [Boiling point ]
479.38°C (rough estimate) | [density ]
0.9492 (rough estimate) | [refractive index ]
1.5640 (estimate) | [storage temp. ]
Store at RT | [solubility ]
ethanol: ≥2mg/mL | [form ]
powder | [pka]
10.20±0.70(Predicted) | [color ]
white to tan | [Optical Rotation]
+25.320 (c 0.7, ethanol) | [LogP]
6.060 (est) |
| Hazard Information | Back Directory | [Description]
Conessine is a naturally occurring steroid alkaloid found in a number of plant species from the Apocynaceae family, which have been used in traditional herbal medicine as a treatment for amoebic dysentery. In a radioligand-based high-throughput screen, conessine demonstrated high affinity for both rat and human histamine H3 receptors (Kis = 5.2 and 24.5 nM, respectively) and high selectivity against histamine receptors H1, H2, and H4. Though conessine potently blocks H3 agonist-stimulated GTPγS binding in cell- and tissue-based functional assays and efficiently crosses the blood-brain barrier, it has a poor rate of CNS clearance. | [Uses]
antiamebic, antibacterial, antineoplastic, anesthetic (local) | [Uses]
Conessine is a steroidal dibasic alkaloid with a rigid steroid-based skeleton. Conessine is a potent and selective histamine H3 receptor antagonist. | [Definition]
ChEBI: A steroid alkaloid that is con-5-enine substituted by a N,N-dimethylamino group at position 3. It has been isolated from the plant species of the family Apocynaceae. | [Biological Activity]
Potent and selective histamine H 3 receptor antagonist (pK i values are 7.61 and 8.27 at rat and human H 3 receptors respectively). A steroidal alkaloid that displays in vitro antiplasmodial activity (IC 50 = 1.04 μ M). Also has high affinity for α 2C adrenoceptors (pK i = 7.98). | [Purification Methods]
It crystallises from acetone, sublimes at 95o/0.01mm and boils at 0.1mm with bath temperature at 220o. The dihydrochloride has m >340o (browns at 235o and decomposes at 338-240o) and has [] D +9.3o (c 2, H2O). [Marshall & Johnson J Am Chem Soc 84 1458 1962, Beilstein 22 III/IV 4382.] | [References]
[1] BINA S SIDDIQUI. Antimicrobial activity of the methanolic bark extract of Holarrhena pubescens (Buch. Ham), its fractions and the pure compound conessine.[J]. Natural Product Research, 2012, 26 11: 987-992. DOI: 10.1080/14786419.2010.537268
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] VIRENDRA K DUA. Anti-malarial property of steroidal alkaloid conessine isolated from the bark of Holarrhena antidysenterica.[J]. Malaria Journal, 2013, 12: 194. DOI: 10.1186/1475-2875-12-194
[4] LIANG SHEN. High-Throughput Screening and Identification of Potent Broad-Spectrum Inhibitors of Coronaviruses.[J]. Journal of Virology, 2019, 93 12. DOI: 10.1128/jvi.00023-19
[5] CHEN ZHAO*. The Alkaloid Conessine and Analogues as Potent Histamine H3 Receptor Antagonists[J]. Journal of Medicinal Chemistry, 2008, 51 17: 5423-5430. DOI: 10.1021/jm8003625 |
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