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PHENSERINE

Product Name
PHENSERINE
CAS No.
101246-66-6
Chemical Name
PHENSERINE
Synonyms
PHENSERINE;(-)-Phenserine;(3as-cis)-amate(ester;(-)-Eseroline phenylcarbamate;(-)-Eseroline phenylcarbamate;(-)-N-PHENYLCARBAMOYLESEROLINE;3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb;1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester);(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate);Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
CBNumber
CB5731231
Molecular Formula
C20H23N3O2
Formula Weight
337.42
MOL File
101246-66-6.mol
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PHENSERINE Property

Melting point:
151-152 °C
Boiling point:
468.7±45.0 °C(Predicted)
Density 
1.228±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
H2O: <2mg/mL
form 
solid
pka
13.05±0.70(Predicted)
color 
off-white
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
UY8586000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P0111
Product name
Phenserine
Purity
≥98% (HPLC), solid
Packaging
25mg
Price
$144
Updated
2024/03/01
Sigma-Aldrich
Product number
P0111
Product name
Phenserine
Purity
≥98% (HPLC), solid
Packaging
100mg
Price
$565
Updated
2024/03/01
Cayman Chemical
Product number
21060
Product name
Phenserine
Purity
≥98%
Packaging
5mg
Price
$36
Updated
2024/03/01
Cayman Chemical
Product number
21060
Product name
Phenserine
Purity
≥98%
Packaging
10mg
Price
$65
Updated
2024/03/01
Cayman Chemical
Product number
21060
Product name
Phenserine
Purity
≥98%
Packaging
25mg
Price
$134
Updated
2024/03/01
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PHENSERINE Chemical Properties,Usage,Production

Uses

Phenserine is inhibitor of amyloid precursor protein (APP). Used in Alzheimer’s treatments.

Biological Activity

Physostigmine analog that inhibits acetylcholinesterase. Inhibits production of amyloid precursor protein (APP) and A β . Improves morris water maze performance of scopolamine-treated rats.

Enzyme inhibitor

This long-acting AChE inhibitor and A?42-lowering agent (FW = 337,42 g/mol; CAS 101246-66-6), also known as (–) -N-phenylcarbamoyl eseroline, is a carbamate analogue of eserine (or physostigmine) that inhibits acetylcholinesterase and is under active investigation for its potential in cholinomimetic therapy to reduce cognitive impairments associated with aging and Alzheimer's Disease. Phenserine is a potent and highly selective AChE inhibitor (IC50 = 22 nM), displaying 70x greater inhibitory action than observed with butyrylcholinesterase, or BChE (IC50 = 1560 nM), both in vitro and in clinical trials for treatment of Alzheimer's disease (1-5). Compared to physostigmine and tacrine, phenserine appears to be less toxic and robustly enhances cognition in animal models. In rats, phenserine achieves maximum acetylcholinesterase inhibition of 73.5% at 5 min, maintaining high and relatively constant inhibition for >8 hours. Phenserine decreased the levels of secreted b-amyloid precursor protein (b- APP) in the cerebrospinal fluid (CSF) of forebrain cholinergic system- lesioned rats, whereas DFP, a relatively non-specific cholinesterase inhibitor, failed to affect CSF levels of secreted b-APP. Such findings suggest that phenserine alters the induction of cortical b-APP mRNAs and increased levels of secreted b-APP in the CSF. Phenserine reduces Ab levels by regulating b-APP translation via a recently described iron regulatory element in the 5'-untranslated region of b-APP mRNA that was previously shown to be up-regulated in the presence of interleukin-1. Other dual AChE/A?42 inhibitors include: rivastigmine, ladostigil, asenapine, phenserine, amitriptyline, clomipramine, doxepin and desipramine. Posiphen, the better-tolerated (+) -enantiomer of phenserine, is devoid of anticholinesterase action, but represses translation of neural α- synuclein, a druggable target in the treatment of Parkinson Disease.

PHENSERINE Preparation Products And Raw materials

Raw materials

Preparation Products

101246-66-6, PHENSERINERelated Search:


  • (3as-cis)-amate(ester
  • 3-b)indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo(phenylcarb
  • (-)-N-PHENYLCARBAMOYLESEROLINE
  • PHENSERINE
  • (3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate)
  • 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester)
  • (-)-Eseroline phenylcarbamate
  • Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
  • (-)-Phenserine
  • (-)-Eseroline phenylcarbamate
  • 101246-66-6