Structure via PubChem · Public domain (PubChem)
cymserine
Sign in to saveCymserine is a drug related to physostigmine, which acts as a reversible cholinesterase inhibitor, with moderate selectivity (15 times) for the plasma cholinesterase enzyme butyrylcholinesterase, and relatively weaker inhibition of the better-known acetylcholinesterase enzyme. This gives it a much more specific profile of effects that may be useful for treating Alzheimer's disease without producing side effects such as tremors, lacrimation, and salivation that are seen with the older nonselective cholinesterase inhibitors currently used for this application, such as donepezil.
Chemical data
- Formula
- C23H29N3O2
- Molecular weight
- 379.5 g/mol
- IUPAC name
- [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-(4-propan-2-ylphenyl)carbamate
- SMILES
- CC(C)C1=CC=C(C=C1)NC(=O)OC2=CC3=C(C=C2)N([C@@H]4[C@]3(CCN4C)C)C
- InChIKey
- NKJRRVBTMYRXRB-GGAORHGYSA-N
- XLogP
- 3.4
- Polar surface area
- 44.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 379.22597716800004
Show 3 more facts
- chemical formula
- C₂₃H₂₉N₃O₂
- canonical SMILES
- CC(C)C1=CC=C(C=C1)NC(=O)OC2=CC3=C(C=C2)N(C4C3(CCN4C)C)C
- isomeric SMILES
- CC(C)c1ccc(NC(=O)Oc2ccc3c(c2)[C@]2(C)CCN(C)[C@@H]2N3C)cc1
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Derivatives
- Metabolism
- References
Cymserine is a drug related to physostigmine, which acts as a reversible cholinesterase inhibitor, with moderate selectivity (15 times) for the plasma cholinesterase enzyme butyrylcholinesterase, and relatively weaker inhibition of the better-known acetylcholinesterase enzyme. This gives it a much more specific profile of effects that may be useful for treating Alzheimer's disease without producing side effects such as tremors, lacrimation, and salivation that are seen with the older nonselective cholinesterase inhibitors currently used for this application, such as donepezil.
==Derivatives== 250px|thumb|left|Derivatives of cymserine A number of cymserine derivatives have been developed with much greater selectivity for butyrylcholinesterase, and both cymserine and several of its analogues have been tested in animals, and found to increase brain acetylcholine levels and produce nootropic effects, as well as reducing levels of amyloid precursor protein and amyloid beta, which are commonly used biomarkers for the development of Alzheimer's disease (potentially indicating the drugs as candidates to be the first medicine capable of stopping, and even reversing, the progression of the disease).
Excerpted from Wikipedia’s “cymserine” article, available under the CC BY-SA 4.0 licence.