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

• ChemBase ID: 856
• Molecular Formular: C15H21N3O2
• Molecular Mass: 275.34614
• Monoisotopic Mass: 275.16337693
• SMILES: O(c1cc2[C@]3([C@H](N(CC3)C)N(c2cc1)C)C)C(=O)NC
• 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-methylcarbamate
• IUPAC Traditional name: physostigmine
• Brand Name: Antilirium; Esromiotin; Ezerin; Fysostigmin; Physostol
• Synonyms: Eserolein, Methylcarbamate; Erserine; Eserine; Eserine Salicylate; Eserine Sulfate; Isopto Eserine; Physostigmine; Physostigmine; ESERINE; Eserine; (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol Methylcarbamate Ester; Synapton; Cogmine; Esromiotin; MCV 4484; NIH 10421; NSC 30782; 伊色林; 毒扁豆碱

Database IDs

• CAS Number: 57-47-6
• EC Number: 200-332-8
• MDL Number: MFCD00151090
• Beilstein Number: 91230
• PubChem SID: 46506998; 160964319; 24869283; 24277867
• PubChem CID: 5983
• CHEBI ID: 27953
• ATC CODE: V03AB19; S01EB05
• CHEMBL: 94
• Chemspider ID: 5763
• DrugBank ID: DB00981
• KEGG ID: D00196
• Unique Ingredient Identifier: 9U1VM840SP
• Wikipedia Title: Physostigmine

CALCULATED PROPERTIES

JChem

• 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: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.8
• LOG S: -2.44
• Solubility (Water): 9.92e-01 g/l

PROPERTIES

Physical Property

• Solubility: 7760 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 102-104 °C(lit.); 102-106 °C; 105-107°C; 96-98°C
• Flash Point: >100 °C; >212 °F
• Optical Rotation: [α]20/D -77±1°, c = 1.7% in chloroform; [α]25/D -116°, c = 1 in benzene
• Hydrophobicity(logP): 1.7

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TJ2100000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Australian Hazchem: 2X
• Risk Statements: 26/28; R:26/28
• Safety Statements: 25-45; S:25-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H330
• GHS Precautionary statements: P260-P264-P284-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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: intravenous, intramuscular, ophthalmic
• Metabolism: Major metabolite: Eseroline
• Legal Status: rx-only (US)
• Pregnancy Category: C (US)
• Gene Information: human ... ACHE(43), APP(351), BCHE(590)mouse ... Ache(11423), Bche(12038), Chrm1(12669)rat ... Ache(83817), Bche(65036), Chrm2(81645)

Product Information

• Purity: ≥98.0% (N); ≥99% (HPLC); 99%
• Empirical Formula (Hill Notation): C15H21N3O2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02151075

Free Base
Crystalline

MP Biomedicals - 05211751

MP Biomedicals Rare Chemical collection

DrugBank - DB00981

• Drug Groups: approved
• Description: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. [PubChem]
• Indication: For the treatment of glaucoma, and in the treatment of severe anticholinergic toxicity.
• Pharmacology: Physostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor which effectively increases the concentration of acetylcholine at the sites of cholinergic transmission. Physostigmine is used to treat glaucoma. Because it crosses the blood-brain barrier, it is also used to treat the central nervous system effects of atropine overdose and other anticholinergic drug overdoses. Physostigmine can reverse both central and peripheral anticholinergia.
• Toxicity: Side effects include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth, blurred vision or change in near or distant vision, and eye pain.
• Affected Organisms: Humans and other mammals
• Biotransformation: Quickly hydrolyzed by cholinesterases
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - E8375

包装
1, 5 g in glass bottle
250 mg in glass bottle
Biochem/physiol Actions
乙酰胆碱酯酶抑制剂越过血脑屏障并与乙酰胆碱酯酶形成缓慢降解的氨基甲酰酶络合物。

Sigma Aldrich - 219312

Biochem/physiol Actions
Acetylcholinesterase inhibitor that crosses the blood-brain barrier and forms a carbamylated enzyme complex with acetyl cholinesterase that degrades slowly.

Sigma Aldrich - 45710

Biochem/physiol Actions
Acetylcholinesterase inhibitor that crosses the blood-brain barrier and forms a carbamylated enzyme complex with acetyl cholinesterase that degrades slowly.

Toronto Research Chemicals - P398500

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)