(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-ol; but-2-enedioic acid

• ChemBase ID: 157729
• Molecular Formular: C17H22N2O5
• Molecular Mass: 334.36698
• Monoisotopic Mass: 334.15287181
• SMILES: C[C@@]12CCN([C@@H]1N(c1c2cc(cc1)O)C)C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: CN1CC[C@@]2([C@H]1N(C)c1c2cc(cc1)O)C.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C13H18N2O.C4H4O4/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13;5-3(6)1-2-4(7)8/h4-5,8,12,16H,6-7H2,1-3H3;1-2H,(H,5,6)(H,7,8)/t12-,13+;/m1./s1
• InChIKey: PBZRRADJWNBPNY-KZCZEQIWSA-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-ol; but-2-enedioic acid
• IUPAC Traditional name: butenedioic acid; eseroline
• Synonyms: (-)-Eseroline fumarate salt; (-)-氧化毒扁豆碱 富马酸盐

Database IDs

• CAS Number: 70310-73-5
• MDL Number: MFCD00055202
• PubChem SID: 162251866; 24277834
• PubChem CID: 16219298

CALCULATED PROPERTIES

• Acid pKa: 10.241504
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.205977
• LogD (pH = 7.4): 2.3517056
• Log P: 2.4315763
• Molar Refractivity: 65.6719 cm^3
• Polarizability: 24.95001 Å^3
• Polar Surface Area: 26.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble (Solutions should be freshly prepared.); 0.1 M NaOH: soluble (Solutions should be freshly prepared.); H2O: soluble (Solutions should be freshly prepared.); methanol: slightly soluble (Solutions should be freshly prepared.)
• Apperance: white solid
• Optical Rotation: [α]23/D -107.9°, c = 0.5 in methanol(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ACHE(43)

Product Information

• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C13H18N2O · C4H4O4

DETAILS

Sigma Aldrich - E100

Biochem/physiol Actions
Metabolite of physostigmine (eserine) that is cytotoxic in several neuronal cell lines; it displays both anti-acetylcholinesterase and opiate agonist activities; potent analgesic.
Caution
Hygroscopic, photosensitive