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

• ChemBase ID: 105904
• Molecular Formular: C22H27N3O5
• Molecular Mass: 413.46688
• Monoisotopic Mass: 413.19507098
• SMILES: OC(=O)c1ccccc1O.CNC(=O)Oc1cc2c(cc1)N(C)[C@H]1N(C)CC[C@@]21C
• Canonical SMILES: OC(=O)c1ccccc1O.CNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN([C@@H]1N2C)C
• InChI: InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1
• InChIKey: HZOTZTANVBDFOF-PBCQUBLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxybenzoic acid (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; 2-hydroxybenzoic acid
• IUPAC Traditional name: physostigmine; salicylic; physostigmine salicylate; physostigmine; salicyclic acid
• Synonyms: Eserine salicylate salt; Physostigmine salicylate salt; ESERINE SALICYLATE SALT; ESERINE SALICYLATE; Eserine Salicylate; physostigmine salicylate; 伊色林 水杨酸盐; 毒扁豆碱 水杨酸盐

Database IDs

• CAS Number: 57-64-7
• EC Number: 200-343-8
• MDL Number: MFCD00135659
• Beilstein Number: 3900576
• PubChem SID: 24869126; 162092847
• PubChem CID: 657348

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: 29.907698 Å^3
• Polar Surface Area: 44.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 181-183 °C; 185°C; 185-187
• Optical Rotation: [α]20/D -77±2°, c = 1% in ethanol

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Protect from light, Avoid excess heat
• RTECS: TJ2450000
• European Hazard Symbols: Nature polluting (N); Highly toxic (T+)
• UN Number: 1544; 3077
• German water hazard class: 3
• Hazard Class: 6.1; 9
• Packing Group: 1; III
• Australian Hazchem: 2X
• Risk Statements: 26/28; R:28
• Safety Statements: 25-45; S:28-29-36/37/39-45
• Emergency Response Guidebook(ERG) Number: 171
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H330
• GHS Precautionary statements: P260-P264-P284-P301 + P310-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 1

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥97.0% (N)
• Salt Data: salicylate
• Empirical Formula (Hill Notation): C15H21N3O2 · C7H6O3

DETAILS

MP Biomedicals - 02195049

Salicylate Salt

MP Biomedicals - 05213767

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 45720

Biochem/physiol Actions
Acetylcholinesterase inhibitor that crosses the blood-brain barrier and forms a carbamylated enzyme complex with acetyl cholinesterase that degrades slowly.
Packaging
1, 5 g in glass bottle