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Physostigmine information


Physostigmine
Clinical data
Trade namesAntilirium
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: C
Routes of
administration
intravenous, intramuscular, ophthalmic
ATC code
  • S01EB05 (WHO) V03AB19 (WHO)
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
MetabolismMajor metabolite: Eseroline
Identifiers
IUPAC name
  • (3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
CAS Number
  • 57-47-6 checkY
PubChem CID
  • 5983
IUPHAR/BPS
  • 6598
DrugBank
  • DB00981 checkY
ChemSpider
  • 5763 checkY
UNII
  • 9U1VM840SP
KEGG
  • D00196 checkY
ChEBI
  • CHEBI:27953 checkY
ChEMBL
  • ChEMBL94 checkY
CompTox Dashboard (EPA)
  • DTXSID3023471 Edit this at Wikidata
ECHA InfoCard100.000.302 Edit this at Wikidata
Chemical and physical data
FormulaC15H21N3O2
Molar mass275.352 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C(Oc1cc2c(cc1)N([C@H]3N(CC[C@@]23C)C)C)NC
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 checkY
  • Key:PIJVFDBKTWXHHD-HIFRSBDPSA-N checkY
  (verify)

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.

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.[1]

  1. ^ Doyle D (January 2009). "Sir Thomas Richard Fraser (1841–1920)" (PDF). JR Coll Physicians Edinb. 39: 283.

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Physostigmine

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Physostigmine (also known as eserine from éséré, the West African name for the Calabar bean) is a highly toxic parasympathomimetic alkaloid, specifically...

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Anticholinergic

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been reported after the rapid administration of physostigmine. Asystole has occurred after physostigmine administration for tricyclic antidepressant overdose...

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Neostigmine

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meaning "new", and "-stigmine", in reference to its parent molecule, physostigmine, on which it is based. It is available as a generic medication. It is...

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Physostigma venenosum

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color. Calabar bean contains physostigmine, a reversible cholinesterase inhibitor alkaloid. The alkaloid physostigmine acts in effect like nerve gas...

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Aminal

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synthesis. Several examples exist in nature. Naturally occurring aminals Physostigmine,a highly toxic cholinesterase inhibitor found in the Calabar bean. Hodgkinsine...

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Atropa belladonna

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has unpredictable effects. The antidote for belladonna poisoning is physostigmine or pilocarpine, the same as for atropine. The potentially deadly ripe...

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Rostral ventrolateral medulla

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nucleus of the spinal cord via reticulospinal tract.[citation needed] Physostigmine, a choline-esterase inhibitor, elevates endogenous levels of acetylcholine...

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Autonomic drug

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the dose can cause side effects like nausea, diarrhea and headache. Physostigmine is an anticholinesterase drug and it is used in treating glaucoma. For...

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Eseroline

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It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline...

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Indole alkaloid

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sign of innocence, otherwise, the person was killed via the action of physostigmine, which is present in the plant and which causes paralysis of the heart...

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Percy Lavon Julian

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drugs from plants. He was the first to synthesize the natural product physostigmine and was a pioneer in the industrial large-scale chemical synthesis of...

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Dimenhydrinate

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needed] An antidote that can be used for dimenhydrinate poisoning is physostigmine. Dimenhydrinate (then known as Compound 1694) was being tested as a...

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Cholinergic

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the elderly. The memory impairments were reversed when treated with physostigmine, a cholinergic agonist. However, reversing memory impairments in AD...

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EPA list of extremely hazardous substances

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oxychloride Phosphorus pentachloride Phosphorus trichloride Physostigmine Physostigmine, salicylate (1:1) Picrotoxin Piperidine Pirimifos-ethyl Plutonium...

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Xerostomia

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lozenges. Physostigmine Gel: A study by Knosravini in 2009 showed a reduction in the oral dryness and a 5 times increase in saliva following physostigmine treatment...

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Rivastigmine

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Yissum for commercial development. It is a semi-synthetic derivative of physostigmine. "Prescription medicines: registration of new generic medicines and...

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Cholinergic crisis

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drugs and mechanical ventilation until the crisis resolves on its own. Physostigmine Asensio JA, Trunkey DD (Apr 20, 2015). Current Therapy of Trauma and...

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Manchineel

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4-dimethylether is present in the leaves, while the fruits possess physostigmine. A poultice of arrowroot (Maranta arundinacea) was used by the Arawak...

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Cholinergic blocking drug

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ingestion. Physostigmine is given only if presenting both peripheral and central signs and symptoms of anticholinergic poisoning. Physostigmine is a central...

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Tricyclic antidepressant overdose

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due to increased risk of respiratory depression. There is no role for physostigmine in the treatment of tricyclic toxicity as it may increase cardiac toxicity...

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Curare

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acetylcholinesterase (AChE) inhibitor (anti-cholinesterase), such as physostigmine or neostigmine. By blocking ACh degradation, AChE inhibitors raise the...

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Parasympathomimetic drug

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Reversible cholinesterase inhibitors Donepezil Edrophonium Neostigmine Physostigmine Pyridostigmine Rivastigmine Tacrine Caffeine (non-competitive) Huperzine...

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Choline

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Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide...

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Eserethole

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Two research groups were independently trying to synthesize the drug physostigmine. One group, led by Percy Julian at Howard University aimed to create...

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Tetrahydrocannabinol

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Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide...

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Caffeine

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Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide...

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Bungarus

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have been successfully treated with cholinesterase inhibitors, such as physostigmine or neostigmine, but success is variable and may be species-dependent...

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