Home > Compound List > Compound details
57-47-6 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:856 http://www.chembase.cn/molecule-856.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
57-47-6
EC Number
200-332-8
MDL Number
MFCD00151090
Beilstein Number
91230
PubChem SID
160964319
24869283
46506998
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.772489  H Acceptors
H Donor LogD (pH = 5.5) 1.1139581 
LogD (pH = 7.4) 2.170551  Log P 2.232533 
Molar Refractivity 78.3968 cm3 Polarizability 29.907698 Å3
Polar Surface Area 44.81 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.8  LOG S -2.44 
Solubility (Water) 9.92e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
7760 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
102-104 °C(lit.) expand Show data source
102-106 °C expand Show data source
105-107°C expand Show data source
96-98°C expand Show data source
Flash Point
>100 °C expand Show data source
>212 °F expand Show data source
Optical Rotation
[α]20/D -77±1°, c = 1.7% in chloroform expand Show data source
[α]25/D -116°, c = 1 in benzene expand Show data source
Hydrophobicity(logP)
1.7 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
TJ2100000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
UN Number
1544 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
I expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
26/28 expand Show data source
R:26/28 expand Show data source
Safety Statements
25-45 expand Show data source
S:25-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
151 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H330 expand Show data source
GHS Precautionary statements
P260-P264-P284-P310 expand Show data source
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 expand Show data source
RID/ADR
UN 1544 6.1/PG 1 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
intravenous, intramuscular, ophthalmic expand Show data source
Metabolism
Major metabolite: Eseroline expand Show data source
Legal Status
rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source
Gene Information
human ... ACHE(43), APP(351), BCHE(590)mouse ... Ache(11423), Bche(12038), Chrm1(12669)rat ... Ache(83817), Bche(65036), Chrm2(81645) expand Show data source
Purity
≥98.0% (N) expand Show data source
≥99% (HPLC) expand Show data source
99% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C15H21N3O2 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02151075 external link
Free Base
Crystalline
MP Biomedicals - 05211751 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00981 external link
Item Information
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 external link
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 external link
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 external link
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 external link
It is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor obtained from the Calabar bean, used to treat glaucoma and delayed gastric emptying.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Engelhart, L., et al.: Arch. Exp. Pathol. Pharmakol., 150, 1 (1930)
  • • Muhtadi, F.J., et al.: Anal. Profiles Drug Subs., 18, 289 (1930)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle