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ChemicalBook--->CAS DataBase List--->546-06-5

546-06-5

546-06-5 Structure

546-06-5 Structure
IdentificationBack 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 PropertiesBack 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 activity]

+25.320 (c 0.7, ethanol)
[LogP]

6.060 (est)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
[RTECS ]

GK7621000
[HS Code ]

2939799090
Hazard InformationBack 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.]
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