(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

• ChemBase ID: 153858
• Molecular Formular: C20H23N3O2
• Molecular Mass: 337.41552
• Monoisotopic Mass: 337.17902699
• SMILES: C[C@@]12CCN([C@@H]1N(c1c2cc(cc1)OC(=O)Nc1ccccc1)C)C
• Canonical SMILES: O=C(Nc1ccccc1)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate
• IUPAC Traditional name: (3aS,8aR)-1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate
• Synonyms: (-)-N-Phenylcarbamoyleseroline; 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-pyrrolo[2,3-b]indol-5-ol phenylcarbamate (ester); Phenserine

Database IDs

• CAS Number: 101246-66-6
• MDL Number: MFCD00672748
• PubChem SID: 162247997
• PubChem CID: 192706

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 3.1347353
• LogD (pH = 7.4): 4.18858
• Log P: 4.2501016
• Molar Refractivity: 99.9552 cm^3
• Polarizability: 37.64495 Å^3
• Polar Surface Area: 44.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 12.859102
• H Acceptors: 4

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL; H2O: <2 mg/mL
• Apperance: off-white solid

Safety Information

• RTECS: UY8586000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H23N3O2

DETAILS

Sigma Aldrich - P0111

Biochem/physiol Actions
(-)-Phenserine, a phenylcarbamate derivative, is a selective, non-competitive inhibitor of acetylcholinesterase (AChE). (-)-Phenserine produces rapid, potent, and long-lasting AChE inhibition, in vivo. It is significantly less toxic than (-)-physostigmine. (-)-Phenserine improves cognitive performance in both young learning-impaired and elderly rats. Reduced secretion of β-amyloid (Abeta) has been observed in cell lines exposed to (-)-phenserine, occurring through translational regulation of β-amyloid precursor protein (beta-APP) mRNA via a non-cholinergic mechanism. These in vitro findings appear to translate in vivo into animal models and humans.