101246-66-6

101246-66-6 structure

Name: Phenserine
Chemical Name: Phenserine,(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate)
CAS Number: 101246-66-6
Molecular Formula: C₂₀H₂₃N₃O₂
Molecular Weight: 337.41600
Catalog: Signaling Pathways Neuronal Signaling AChE
Create Date: 2018-06-27 19:11:53
Modify Date: 2024-01-02 21:30:36
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].

Name	Phenserine,(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol5-(N-phenylcarbamate)

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.

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

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

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

103-71-9

469-22-7

101246-66-6

Literature: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

153109-52-5

101246-66-6

Literature: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

65166-97-4

101246-66-6

Literature: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

799561-30-1

101246-66-6

Literature: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

799561-17-4

101246-66-6

Literature: Huang, Audris; Kodanko, Jeremy J.; Overman, Larry E. Journal of the American Chemical Society, 2004 , vol. 126, # 43 p. 14043 - 14053

Precursor 4
103-71-9 469-22-7 65166-97-4 799561-30-1
DownStream 0

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