physostigmine

Also known as Antilirium®, eserine, physostigmine salicylate, Physostol, Antilirium, Eserine, esromiotin

Physostigmine (also known as eserine from éséré, the West African name for the Calabar bean) is a highly toxic parasympathomimetic alkaloid, specifically, a reversible cholinesterase inhibitor. It occurs naturally in the Calabar bean and the fruit of the Manchineel tree.

Key facts

Drug.Watchedfields: changed
Drug.class: Cholinesterase inhibitor
Drug.verifiedrevid: 464206065
Drug.IUPAC_name: (3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
Drug.image: Physostigmin.svg
Drug.image_class: skin-invert-image
Drug.image2: Physostigmine ball-and-stick model from xtal 2002.png
Drug.image_class2: bg-transparent
Drug.tradename: Antilirium
Drug.pregnancy_AU: C
Drug.pregnancy_US: C
Drug.legal_US: Rx-only
Drug.routes_of_administration: Intravenous, intramuscular, ophthalmic
Drug.metabolism: Major metabolite: Eseroline
Drug.IUPHAR_ligand: 6598
Drug.CAS_number: 57-47-6
Drug.ATC_prefix: S01
Drug.ATC_suffix: EB05

via Wikipedia infobox

Chemical data

Formula: C15H21N3O2
Molecular weight: 275.35 g/mol
IUPAC name: [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-N
XLogP: 0.7
Polar surface area: 44.8 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

7,478 papers

Adverse Effects of Physostigmine.Journal of medical toxicology : official journal of the American College of Medical Toxicology · 2019
Physostigmine: is there a role for this antidote in pediatric poisonings?Current opinion in pediatrics · 2007
Physostigmine as a treatment for gamma-hydroxybutyrate toxicity: a review.Journal of toxicology. Clinical toxicology · 2002
Physostigmine antagonizes ketamine.Anesthesia and analgesia · 1980
Assessing physostigmine's contraindication in cyclic antidepressant ingestions.The Journal of emergency medicine · 2003

via PubMed

Wikidata facts

Mass: 275.163377

Show 5 more facts

chemical formula: C₁₅H₂₁N₃O₂
isomeric SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
Commons category: Physostigmine
defined daily dose: 0.4

Sources (4)

via Wikidata · CC0

~11 min read

Article

11 sections

Contents

Medical uses
Pharmacology
Bioactivity
Side effects
Synthesis
Biosynthesis
History
The Calabar bean
Western medicine's discovery
See also
References

The chemical was synthesized for the first time in 1935 by Percy Lavon Julian and Josef Pikl. It is available in the U.S. under the trade names Antilirium and Isopto Eserine, and as eserine salicylate and eserine sulfate. Today, physostigmine is most commonly used for its medicinal value. However, before its discovery by Sir Robert Christison in 1846, it was much more prevalent as an ordeal poison. The positive medical applications of the drug were first suggested in the gold medal-winning final thesis of Thomas Richard Fraser at the University of Edinburgh in 1862.