(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-(2H3)methylcarbamate

• ChemBase ID: 176712
• Molecular Formular: C15H21N3O2
• Molecular Mass: 275.34614
• Monoisotopic Mass: 275.16337693
• SMILES: [C@@H]12N(c3c([C@@]1(CCN2C)C)cc(cc3)OC(=O)NC)C
• Canonical SMILES: CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
• InChI: InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
• InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-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-(^2H₃)methylcarbamate
• IUPAC Traditional name: (3aS,8aR)-1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-yl N-(^2H₃)methylcarbamate
• Synonyms: (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol Methylcarbamate Ester-d3; Eserine-d3; Synapton-d3; Physostigmine-d3

Database IDs

• PubChem SID: 164232622
• PubChem CID: 45040248

CALCULATED PROPERTIES

• Acid pKa: 14.772489
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.1139581
• LogD (pH = 7.4): 2.170551
• Log P: 2.232533
• Molar Refractivity: 78.3968 cm^3
• Polarizability: 29.907719 Å^3
• Polar Surface Area: 44.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Benzene; Chloroform,
• Apperance: Crystalline Solid
• Melting Point: 105-106°C

DETAILS

Toronto Research Chemicals - P398502

It is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor obtained from the Calabar bean, used to treat glaucoma and delayed gastric emptying.

REFERENCES

• Engelhart, L., et al.: Arch. Exp. Pathol. Pharmakol., 150, 1 (1930)
• Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 18, 289 (1930)