P0111

Sigma-Aldrich

Phenserine

≥98% (HPLC), solid

Synonym(s):
(−)-N-Phenylcarbamoyleseroline, 1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester)
Empirical Formula (Hill Notation):
C20H23N3O2
CAS Number:
Molecular Weight:
337.42
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

color

off-white

solubility

H2O: <2 mg/mL
DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

[H][C@]12N(C)CC[C@@]1(C)c3cc(OC(=O)Nc4ccccc4)ccc3N2C

InChI

1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)/t18-,20+/m1/s1

InChI key

PBHFNBQPZCRWQP-QUCCMNQESA-N

Packaging

25, 100 mg in glass bottle

Biochem/physiol Actions

(-)-Phenserine, a phenylcarbamate derivative, is a selective, non-competitive inhibitor of acetylcholinesterase (AChE). (-)-Phenserine produces rapid, potent, and long-lasting AChE inhibition, in vivo. It is significantly less toxic than (-)-physostigmine. (-)-Phenserine improves cognitive performance in both young learning-impaired and elderly rats. Reduced secretion of β-amyloid (Abeta) has been observed in cell lines exposed to (-)-phenserine, occurring through translational regulation of β-amyloid precursor protein (beta-APP) mRNA via a non-cholinergic mechanism. These in vitro findings appear to translate in vivo into animal models and humans.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Ayodeji A Asuni et al.
Annals of neurology, 75(5), 684-699 (2014-04-02)
Proteolytic cleavage of the amyloid precursor protein (APP) generates β-amyloid (Aβ) peptides. Prolonged accumulation of Aβ in the brain underlies the pathogenesis of Alzheimer disease (AD) and is regarded as a principal target for development of disease-modifying therapeutics. Using Chinese...
Articles
Acetylcholine is synthesized from acetyl coenzyme A and choline by the enzyme choline acetyltransferase. In addition to its synthesis in the liver, choline employed in acetylcholine production is derived from dietary sources.
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