PHENSERINE

Product Name: PHENSERINE
CAS No.: 101246-66-6
Chemical Name: PHENSERINE
Synonyms: PHENSERINE;(-)-Phenserine;(3as-cis)-amate(ester;(-)-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
pka: 13.05±0.70(Predicted)
form: solid
color: off-white
Water Solubility: H2O: <2mg/mL
DMSO: >5mg/mL
InChI: 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
InChIKey: PBHFNBQPZCRWQP-QUCCMNQESA-N
SMILES: N1(C)C2=C(C=C(OC(=O)NC3=CC=CC=C3)C=C2)[C@]2(C)CCN(C)[C@]12[H]

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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: $148
Updated: 2025/07/31

Sigma-Aldrich

Product number: P0111
Product name: Phenserine
Purity: ≥98% (HPLC), solid
Packaging: 100mg
Price: $581
Updated: 2025/07/31

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.

in vivo

Phenserine (1-4 mg/kg; intraperitoneal injection; for 4 days; male Fischer-344 rats) treatment improves learning when cholinergic function has been impaired in a spatial memory task^[3].

Animal Model:	Male Fischer-344 rats (5 months old) induced by scopolamine^[3]
Dosage:	1 mg/kg, 2 mg/kg, 4 mg/kg
Administration:	Intraperitoneal injection; for 4 days
Result:	Improved morris water maze performance of scopolamine-treated rats..

IC 50

AChE

PHENSERINE Preparation Products And Raw materials

Raw materials

Preparation Products

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PHENSERINE Suppliers

China 33 Switzerland 1 The Netherlands 1 United Kingdom 1 United States 13 USA 1 Global 50

3B Pharmachem (Wuhan) International Co.,Ltd.

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EMMX Biotechnology LLC

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Alfa Chemistry

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TargetMol Chemicals Inc.

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Nextpeptide Inc

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Jiangsu Hongmin Pharmaceutical Co., Ltd.

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101246-66-6, PHENSERINERelated Search:

PHYSOSTIGMINE AMINOCARB 1H-Indol-2-amine 3-(3-METHOXYPHENYL)PYRROLIDINE PHENSERINE

(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

101246-66-6