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
• Article Data: 4

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

Description

A pregnene type alkaloid found in the bark and seeds of Holarrhena antidysenterica Wall., the base yields a hydrate, m.p. 88-92°C and has [α]25D + 30.0° (aqueous EtOH). It is freely soluble in most organic solvents. It yields a series of crystalline salts and derivatives, e.g. the hydrochloride, m.p. 334-335°C (dec.); hydrobromide, m.p. 344°C; hydriodide, m.p. 316°C; platinichloride, m.p. 285°C (dec.); methiodide, m.p. 290°C (dec.) and the picrate, m.p. 198-200°C. The N-acetyl derivative has also been prepared, m.p. 161°C yielding a hydrochloride, m.p. 325-6°C, as has the benzoyl compound, m.p. l59-l60°C, also forming a hydrochloride, m.p. 325-6°C (dec.). On methylation, the alkaloid yields conessine and heating with dilute H2S04 isomerizes the base to isonorisoconessine, [0:]5S + 101 ° (EtOH), furnishing a hydriodide, m.p. 289°C (dec.) and a picrate, m.p. 166°C.

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

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