Home Indole and Oxindoles 101246-66-6
101246-66-6,MFCD00672748
Catalog No.:AA0003Z2
101246-66-6 | Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
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5mg
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10mg
≥98%
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$123.00   $86.00
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25mg
≥98%
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50mg
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Technical Information
Catalog Number:
AA0003Z2
Chemical Name:
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-
CAS Number:
101246-66-6
Molecular Formula:
C20H23N3O2
Molecular Weight:
337.4155
MDL Number:
MFCD00672748
IUPAC Name:
[(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate
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
InChI Key:
PBHFNBQPZCRWQP-QUCCMNQESA-N
SMILES:
O=C(Nc1ccccc1)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
UNII:
SUE285UG3S
Properties
Computed Properties
 
Complexity:
507  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
337.179g/mol
Formal Charge:
0
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
337.423g/mol
Monoisotopic Mass:
337.179g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
44.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3  

Synonyms
 
N-phenylcarbamoyl eseroline 
N-phenylcarbamoyleseroline 
SUE285UG3S 
CHEMBL74926 
(-)-N-Phenylcarbamoyleseroline 
MFCD00672748 
phenserine.tartaric acid 
1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester) 
Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, phenylcarbamate (ester), (3aS-cis)- 
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aR,8aS)- 
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-, (2R,3R)-2,3-dihydroxybutanedioate (1:1);Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)-, (2R,3R)-2,3-dihydroxybutanedioate (1:1) 
(+/-)-Phenserine 
phenserine 
Phenserine, (+/-)- 
Phenserine (racemate) [MI] 
116839-68-0 
AC1L4USL 
(3as,8ar)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl phenylcarbamate 
AC1Q60X9 
SCHEMBL1537384 
BDBM10958 
CTK3J9631 
PBHFNBQPZCRWQP-QUCCMNQESA-N 
posiphen 
HMS3261J07 
Pyrrolo[2,3-b]indol-5-ol,1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)- 
Tox21_500523 
ZINC52968892 
AKOS015967321 
Phenserine, >=98% (HPLC), solid 
CCG-221827 
DB04892 
LP00523 
NCGC00163250-01 
Phenserine 
NCGC00163250-02 
NCGC00261208-01 
159652-53-6 
Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aR,8aS)-rel- 
Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, phenylcarbamate (ester), cis-(+/-)- 
LS-139390 
RT-015025 
B7235 
96623-EP2287163A1 
96623-EP2305678A1 
101246-66-6 
J-000348 
BRD-K46580984-001-01-0 
UNII-N8142NV8UM component PBHFNBQPZCRWQP-QUCCMNQESA-N 
[(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-phenylcarbamate 
(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol 5-(N-phenylcarbamate) 
(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl 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)- 
Phenserine tartrate 
Phenserine (racemate) 
N-phenylcarbamoyleseroline 
UNII-SUE285UG3S 
UNII-N8142NV8UM 
N-phenylcarbamoyl eseroline 
D0SR4T 
N8142NV8UM 
KST-1A0500 
AR-1A4082 
CID192706 
C20-H23-N3-O2 
(-)-5-O-(N-Phenylcarbamoyl)eseroline L-tartrate 
C092280 
posiphen 
109349-04-4 
(3aS,8aR)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyr-rolo[2,3-b]indol-5-ol phenylcarbamate (ester) 
N-Phenylcarbamic acid (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl ester L-tartrate 
pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-phenylcarbamate), (3aS,8aR)- 
(-)-Eseroline phenylcarbamate 
(-)-Phenserine 
Literature

Title: Posiphen as a candidate drug to lower CSF amyloid precursor protein, amyloid-β peptide and τ levels: target engagement, tolerability and pharmacokinetics in humans.

Journal: Journal of neurology, neurosurgery, and psychiatry 20120901

Title: Acetylcholinesterase deficiency contributes to neuromuscular junction dysfunction in type 1 diabetic neuropathy.

Journal: American journal of physiology. Endocrinology and metabolism 20120815

Title: Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities.

Journal: Bioorganic & medicinal chemistry 20120815

Title: Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction.

Journal: The Journal of organic chemistry 20120106

Title: Acetylcholinesterase inhibition ameliorates deficits in motivational drive.

Journal: Behavioral and brain functions : BBF 20120101

Title: Lithium, phenserine, memantine and pioglitazone reverse memory deficit and restore phospho-GSK3β decreased in hippocampus in intracerebroventricular streptozotocin induced memory deficit model.

Journal: Brain research 20111202

Title: Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: reaction development and applications.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20110301

Title: Cholinesterase inhibitors improve both memory and complex learning in aged beagle dogs.

Journal: Journal of Alzheimer's disease : JAD 20110101

Title: Novel carbamates as orally active acetylcholinesterase inhibitors found to improve scopolamine-induced cognition impairment: pharmacophore-based virtual screening, synthesis, and pharmacology.

Journal: Journal of medicinal chemistry 20100909

Title: Synthesis of physostigmine analogues and evaluation of their anticholinesterase activities.

Journal: Bioorganic & medicinal chemistry letters 20100301

Title: Phenserine efficacy in Alzheimer's disease.

Journal: Journal of Alzheimer's disease : JAD 20100101

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: The perils of Alzheimer's drug development.

Journal: Current Alzheimer research 20090201

Title: Accommodation of physostigmine and its analogues by acetylcholinesterase is dominated by hydrophobic interactions.

Journal: The Biochemical journal 20090101

Title: How to approach Alzheimer's disease therapy using stem cell technologies.

Journal: Journal of Alzheimer's disease : JAD 20081001

Title: Effect of phenserine treatment on brain functional activity and amyloid in Alzheimer's disease.

Journal: Annals of neurology 20080501

Title: Phenserine.

Journal: Expert opinion on investigational drugs 20070701

Title: Preclinical investigation of the topical administration of phenserine: transdermal flux, cholinesterase inhibition, and cognitive efficacy.

Journal: The Journal of pharmacology and experimental therapeutics 20070401

Title: Total synthesis of (+/-) -phenserine via [4+1] cyclization of a bis(alkylthio)carbene and an indole isocyanate.

Journal: Organic letters 20070329

Title: The experimental Alzheimer's disease drug posiphen [(+)-phenserine] lowers amyloid-beta peptide levels in cell culture and mice.

Journal: The Journal of pharmacology and experimental therapeutics 20070101

Title: Differential effects of two hexahydropyrroloindole carbamate-based anticholinesterase drugs on the amyloid beta protein pathway involved in Alzheimer's disease.

Journal: Neuromolecular medicine 20070101

Title: Kinetics of human serum butyrylcholinesterase and its inhibition by a novel experimental Alzheimer therapeutic, bisnorcymserine.

Journal: Journal of Alzheimer's disease : JAD 20060901

Title: Identification of novel small molecule inhibitors of amyloid precursor protein synthesis as a route to lower Alzheimer's disease amyloid-beta peptide.

Journal: The Journal of pharmacology and experimental therapeutics 20060801

Title: Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H-indoles using trialkylboranes.

Journal: Journal of the American Chemical Society 20060517

Title: Novel cholinesterase inhibitors as future effective drugs for the treatment of Alzheimer's disease.

Journal: Expert opinion on investigational drugs 20060101

Title: Anticholinesterase and pharmacokinetic profile of phenserine in healthy elderly human subjects.

Journal: Current Alzheimer research 20051001

Title: An overview of phenserine tartrate, a novel acetylcholinesterase inhibitor for the treatment of Alzheimer's disease.

Journal: Current Alzheimer research 20050701

Title: Phenserine Axonyx.

Journal: Current opinion in investigational drugs (London, England : 2000) 20050701

Title: Further evidence for the cholinergic hypothesis of aging and dementia from the canine model of aging.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20050301

Title: Novel anticholinesterases based on the molecular skeletons of furobenzofuran and methanobenzodioxepine.

Journal: Journal of medicinal chemistry 20050224

Title: The cholinesterase inhibitor, phenserine, improves Morris water maze performance of scopolamine-treated rats.

Journal: Life sciences 20050121

Title: The integrated role of desferrioxamine and phenserine targeted to an iron-responsive element in the APP-mRNA 5'-untranslated region.

Journal: Annals of the New York Academy of Sciences 20041201

Title: Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine.

Journal: Journal of the American Chemical Society 20041103

Title: Sensitivity of [11C]N-methylpyrrolidinyl benzilate ([11C]NMPYB) to endogenous acetylcholine: PET imaging vs tissue sampling methods.

Journal: Nuclear medicine and biology 20040501

Title: (R)-N-[11C]methyl-3-pyrrolidyl benzilate, a high-affinity reversible radioligand for PET studies of the muscarinic acetylcholine receptor.

Journal: Synapse (New York, N.Y.) 20020701

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Methyl analogues of the experimental Alzheimer drug phenserine: synthesis and structure/activity relationships for acetyl- and butyrylcholinesterase inhibitory action.

Journal: Journal of medicinal chemistry 20011122

Title: Acetylcholinesterase inhibition increases in vivo N-(2-[18F]fluoroethyl)-4-piperidyl benzilate binding to muscarinic acetylcholine receptors.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20010201

Title: Phenserine (Axonyx/NIH).

Journal: IDrugs : the investigational drugs journal 20001001

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