Physostigmine

• CAT Number: R047280
• CAS Number: 57-47-6
• Molecular Formula: C15H21N3O2
• Molecular Weight: 275.352
• Purity: ≥95%
• Synonyms: (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-ol Methylcarbamate Ester; Eserine; Synapton; Cogmine; Eserine; Esromiotin; MCV 4484; NIH 10421; NSC 30782
• Target: Cholinesterase Inhibitor
• Storage: -20°C
• IUPAC Name: [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
• 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
• SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C

Physostigmine is an alkaloid and noted to act as a potent and reversible inhibitor of cholinesterase. Physostigmine is also reported to form a slowly degrading carbamylated enzyme complex with AChE (acetylcholinesterase). This compound has been used as a positive control in a study investigating acetylcholinesterase inhibitors for potential antihelminthic drug targets.

Reference

1:The impact of bilateral vagotomy on the physostigmine-induced airway constriction in ferrets. Neziri B, Daci A, Krasniqi S, Sopi R, Haxhiu MA.Respir Physiol Neurobiol. 2017 Apr 23;242:102-107. doi: 10.1016/j.resp.2017.04.005. [Epub ahead of print] PMID: 28445778 2:The E Loop of the Transmitter Binding Site Is a Key Determinant of the Modulatory Effects of Physostigmine on Neuronal Nicotinic α4β2 Receptors. Jin X, McCollum MM, Germann AL, Akk G, Steinbach JH.Mol Pharmacol. 2017 Feb;91(2):100-109. doi: 10.1124/mol.116.106484. Epub 2016 Nov 28. PMID: 27895161 3:Reversal of cardiac vagal effects of physostigmine by adjunctive muscarinic blockade. Winter J, Cook AR, Patient DH, Emmett SR, Tattersall J, Shattock MJ.Neurotoxicology. 2016 Dec;57:174-182. doi: 10.1016/j.neuro.2016.09.020. Epub 2016 Sep 28. PMID: 27693445 4:Physostigmine and Methylphenidate Induce Distinct Arousal States During Isoflurane General Anesthesia in Rats. Kenny JD, Chemali JJ, Cotten JF, Van Dort CJ, Kim SE, Ba D, Taylor NE, Brown EN, Solt K.Anesth Analg. 2016 Nov;123(5):1210-1219. PMID: 26991753 5:Donepezil: It is time to replace physostigmine in Anesthesiology. Mellios G.Med Hypotheses. 2016 Sep;94:23-4. doi: 10.1016/j.mehy.2016.06.015. Epub 2016 Jun 11. No abstract available. PMID: 27515193 6:Increased cell proliferation and neural activity by physostigmine in the telencephalon of adult zebrafish. Lee Y, Lee B, Jeong S, Park JW, Han IO, Lee CJ.Neurosci Lett. 2016 Aug 26;629:189-95. doi: 10.1016/j.neulet.2016.07.001. Epub 2016 Jul 1. PMID: 27378362 7:Neuroinflammation: effect of surgical stress compared to anaesthesia and effect of physostigmine. Plaschke K, Weigand MA, Fricke F, Kopitz J.Neurol Res. 2016 May;38(5):397-405. doi: 10.1080/01616412.2016.1173889. Epub 2016 Apr 20. PMID: 27095151 8:Species- and concentration-dependent differences of acetyl- and butyrylcholinesterase sensitivity to physostigmine and neostigmine. Bitzinger DI, Gruber M, Tümmler S, Michels B, Bundscherer A, Hopf S, Trabold B, Graf BM, Zausig YA.Neuropharmacology. 2016 Oct;109:1-6. doi: 10.1016/j.neuropharm.2016.01.005. Epub 2016 Jan 6. PMID: 26772968 9:Delirium Accompanied by Cholinergic Deficiency and Organ Failure in a 73-Year-Old Critically Ill Patient: Physostigmine as a Therapeutic Option. Zujalovic B, Barth E.Case Rep Crit Care. 2015;2015:793015. doi: 10.1155/2015/793015. Epub 2015 Oct 13. PMID: 26550498 Free PMC Article10:Prolonged Antimuscarinic Delirium in a Child Due to Benztropine Exposure Treated With Multiple Doses of Physostigmine. Thornton SL, Farnaes L, Minns A.Pediatr Emerg Care. 2016 Apr;32(4):243-5. doi: 10.1097/PEC.0000000000000503. PMID: 26383155