Phenserine

Names

[ Name ]:
Phenserine

Biological Activity

[Description]:

Phenserine ((-)-Eseroline phenylcarbamate) is a derivative of Physostigmine and is a potent, noncompetitive, long-acting and selective AChE inhibitor. Phenserine reduces β-amyloid precursor protein (APP) and β-amyloid peptide (Aβ) formation. Phenserine improves cognitive performance and attenuates the progression of Alzheimer's disease[1][2][3].

[Related Catalog]:

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> AChE

[Target]

AChE; β-amyloid precursor protein; β-amyloid peptide[1]

[In Vitro]

Phenserine (1-25 μM; 48 hours; CHO APP751SW cells) treatment CHO APP751SW cell shows 18.6% reduction in cells treated with 10 μM of Phenserine, while 25 μM concentration of Phenserine reduces APP level by 51.4%[2]. Western Blot Analysis[2] Cell Line: CHO APP751SW cells Concentration: 1 μM, 2.5 μM, 5 μM, 10 μM, 25 μM Incubation Time: 48 hours Result: 8.6% reduction in cells treated with 10 μM, while 25 μM concentration reduces APP level by 51.4%.

[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..

[References]

[1]. Klein J. Phenserine. Expert Opin Investig Drugs. 2007 Jul;16(7):1087-97.

[2]. Asuni AA, et al. Modulation of amyloid precursor protein expression reduces β-amyloid deposition in a mouse model. Ann Neurol. 2014 May;75(5):684-99.

[3]. Janas AM, et al. The cholinesterase inhibitor, phenserine, improves Morris water maze performance of scopolamine-treated rats. Life Sci. 2005 Jan 21;76(10):1073-81.

Chemical & Physical Properties

[ Density]:
1.228g/cm3

[ Boiling Point ]:
468.7ºC at 760mmHg

[ Molecular Formula ]:
C₂₀H₂₃N₃O₂

[ Molecular Weight ]:
337.41600

[ Flash Point ]:
237.3ºC

[ Exact Mass ]:
337.17900

[ PSA ]:
44.81000

[ LogP ]:
3.74250

[ Vapour Pressure ]:
5.85E-09mmHg at 25°C

[ Index of Refraction ]:
1.633

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY8586000

CHEMICAL NAME :: Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, phenylcarbamate (ester), (3aS-cis)-

CAS REGISTRY NUMBER :: 101246-66-6

LAST UPDATED :: 199703

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C20-H23-N3-O2

MOLECULAR WEIGHT :: 337.46

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: >20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5409948

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
UY8586000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Modulation of amyloid precursor protein expression reduces β-amyloid deposition in a mouse model.

Ann. Neurol. 75(5) , 684-99, (2014)

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 reg...

Related Compounds

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