Physostigmine

Physostigmine

Clinical data
Trade names	Antilirium
AHFS/Drugs.com	Monograph
Pregnancy category	AU: C
Routes of administration	intravenous, intramuscular, ophthalmic
ATC code	S01EB05 (WHO) V03AB19 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Metabolism	Major 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 Y
PubChem CID	5983
IUPHAR/BPS	6598
DrugBank	DB00981 Y
ChemSpider	5763 Y
UNII	9U1VM840SP
KEGG	D00196 Y
ChEBI	CHEBI:27953 Y
ChEMBL	ChEMBL94 Y
CompTox Dashboard (EPA)	DTXSID3023471
ECHA InfoCard	100.000.302
Chemical and physical data
Formula	C15H21N3O2
Molar mass	275.352 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 Y Key:PIJVFDBKTWXHHD-HIFRSBDPSA-N Y
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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, 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]