468-36-0

Basic information

• Product Name: N-Methylconanin-5-en-3β-amine
• Synonyms: Isoconessimine;Kurchine;N-Methylconanin-5-en-3β-amine;Norconessine
• CAS NO: 468-36-0
• Molecular Formula: C₂₃H₃₈N₂
• Molecular Weight: 342.56122
• Mol File: 468-36-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Methylconanin-5-en-3β-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylconanin-5-en-3β-amine(468-36-0)
• EPA Substance Registry System: N-Methylconanin-5-en-3β-amine(468-36-0)

Safety Data

• Hazardous Substances Data: 468-36-0(Hazardous Substances Data)

Usage

Uses

Unfortunately, the provided materials do not mention any specific applications or uses for N-Methylconanin-5-en-3β-amine.

References

Siddiqui.,J. Ind. Chern. Soc., 11,283 (1934) Siddiqui, Siddiqui., ibid, 11,787 (1934) Haworth, McKenna, Whitfield.,J. Chern. Soc., 1102 (1953)

Upstream product

• 510-73-6 conessine 

Relevant articles and documents

Synthesis, biological activity evaluation and molecular modeling study on the new isoconessimine derivatives as acetylcholinesterase inhibitors

New isoconessimine derivatives were synthesized from conessine (1) and evaluated as acetylcholinesterase (AChE) inhibitors. The derivatives were prepared via two reaction steps, N-demethylation and nucleophilic substitution. All of the synthesized derivatives exhibited more potential anti- acetylcholinesterase activities than conessine (1) (IC50=16 μmol·L-1) and isoconessimine (2) (IC50>300 μmol·L-1). Compound 7b (3β-[methyl-[2-(4-nitrophenoxy) ethyl]amino]con-5-enine) showed the most potent inhibitory activity with an IC50 of 110 nmol/L which is close to that of reference compound huperzine A (IC50=70 nmol/L). The mode of AChE inhibition by 7b was reversible and non-competitive. In addition, molecular modeling was performed to explore the binding mode of inhibitor 7b at the active site of AChE and the results showed that 7b could be docked into the acetylcholinesterase active site and compound 7b had hydrophobic interactions with Trp279 and Leu282. A series of 3-N-aryloxyethyl substitutional isoconessimine derivatives were synthesized and evaluated as acetylcholinesterase (AChE) inhibitors. All of the synthesized derivatives exhibited potential anti-acetylcholinesterase activities with IC50 values at micromolar to sub-micromolar range. 7b showed the most potent inhibitory activity with an IC50of 110 nmol/L. The molecular docking results showed that 7b can be well docked into the active site of acetylcholinesterase. Copyright

The alkaloid conessine and analogues as potent histamine H3 receptor antagonists

The naturally occurring alkaloid, conessine (6), was discovered to bind to histamine H3 receptors in a radioligand-based high-throughput screen. Conessine displayed high affinity at both rat and human H3 receptors (pKi = 7.61 and 8.27) and generally high selectivity against other sites, including histamine receptors H1, H2, and H 4. Conessine was found to efficiently penetrate the CNS and reach very high brain concentrations. Although the very slow CNS clearance and strong binding to adrenergic receptors discouraged focus on conessine itself for further development, its potency and novel steroid-based skeleton motivated further chemical investigation. Modification based on introducing diversity at the 3-nitrogen position generated a new series of H3 antagonists with higher in vitro potency, improved target selectivity, and more favorable drug-like properties. One optimized analogue (13c) was examined in detail and was found to be efficacious in animal behavioral model of cognition.

Azacyclosteroid histamine-3 receptor ligands

Azacyclosteroid histamine-3 receptor ligands, pharmaceutical compositions comprising such compounds, and methods for using such compounds and compositions are described herein.

AZACYCLOSTEROID HISTAMINE-3 RECEPTOR LIGANDS

Azacyclosteroid histamine-3 receptor ligands, pharmaceutical compositions comprising such compounds, and methods for using such compounds and compositions are described herein.