P0111

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: 101246-66-6
• Molecular Weight: 337.42
• MDL number: MFCD00672748
• UNSPSC Code: 12352200
• PubChem Substance ID: 329820018
• NACRES: NA.77

Properties

• 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

Description

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 featured on the Acetylcholine Synthesis and Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves