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MedKoo Cat#: 525986 | Name: Physostigmine salicylate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Physostigmine salicylate is a reversible cholinesterase inhibitor, a parasympathomimetic alkaloid. 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.

Chemical Structure

Physostigmine salicylate
Physostigmine salicylate
CAS#57-64-7 (salicylate)

Theoretical Analysis

MedKoo Cat#: 525986

Name: Physostigmine salicylate

CAS#: 57-64-7 (salicylate)

Chemical Formula: C22H27N3O5

Exact Mass: 0.0000

Molecular Weight: 413.47

Elemental Analysis: C, 63.91; H, 6.58; N, 10.16; O, 19.35

Price and Availability

Size Price Availability Quantity
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
200mg USD 2,250.00 2 Weeks
500mg USD 3,450.00 2 Weeks
1g USD 4,950.00 2 Weeks
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Related CAS #
64-47-1 (sulfate) 57-47-6 (free base) 6091-12-9 (HCl) 6091-13-0 (HBr) 57-64-7 (salicylate) 6091-11-8 (HI)
Synonym
Physostigmine salicylate; Antilirium; AR-44; CCRIS 3405; EINECS 200-343-8; Isopto Eserine; Physostigmine monosalicylate.
IUPAC/Chemical Name
Benzoic acid, 2-hydroxy-, compd. with (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl methylcarbamate (1:1)
InChi Key
HZOTZTANVBDFOF-PBCQUBLHSA-N
InChi Code
InChI=1S/C15H21N3O2.C7H6O3/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2;8-6-4-2-1-3-5(6)7(9)10/h5-6,9,13H,7-8H2,1-4H3,(H,16,19);1-4,8H,(H,9,10)/t13-,15+;/m1./s1
SMILES Code
O=C(O)C1=CC=CC=C1O.O=C(OC2=CC3=C(N(C)[C@]4([H])[C@@]3(C)CCN4C)C=C2)NC
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Physostigmine salicylate (Eserine salicylate) is a reversible acetylcholinesterase (AChE) inhibitor.
In vitro activity:
The present study was performed to investigate a possible pre- and post-treatment effect of physostigmine on soman-inhibited human AChE given at different time intervals before or after perfusion with soman by using a well-established dynamically working in vitro model for real-time analysis of erythrocyte and muscle AChE. The major findings were that prophylactic physostigmine prevented complete inhibition of AChE by soman and resulted in partial spontaneous recovery of the enzyme by de-carbamylation. Physostigmine given as post-treatment resulted in a time-dependent reduction of the protection from soman inhibition and recovery of AChE. Reference: Toxicol Appl Pharmacol. 2011 May 15;253(1):7-13. https://pubmed.ncbi.nlm.nih.gov/21402092/
In vivo activity:
Administration of physostigmine and donepezil improved deficits in contextual and cued memory in Tg(+) mice so that their behaviors became more similar to Tg(-) mice. However, administration of physostigmine and donepezil tended to improve cued memory and deficits in spatial learning in both Tg(+) and Tg(-) mice. Physostigmine administration demonstrated more prominent effects in improving contextual memory than donepezil, while donepezil was more effective than physostigmine in improving deficits in the acquisition of the spatial memory paradigm. Reference: Psychopharmacology (Berl). 2005 Aug;181(1):145-52. https://pubmed.ncbi.nlm.nih.gov/15778881/
Solvent mg/mL mM comments
Solubility
DMF 30.0 72.56
DMSO 10.0 24.19
Ethanol 1.0 2.42
PBS (pH 7.2) 1.0 2.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 413.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Herkert NM, Schulz S, Wille T, Thiermann H, Hatz RA, Worek F. Pre- and post-treatment effect of physostigmine on soman-inhibited human erythrocyte and muscle acetylcholinesterase in vitro. Toxicol Appl Pharmacol. 2011 May 15;253(1):7-13. doi: 10.1016/j.taap.2011.03.005. Epub 2011 Mar 11. PMID: 21402092. 2. Svobodová L, Krůsek J, Hendrych T, Vyskocil F. Physostigmine modulation of acetylcholine currents in COS cells transfected with mouse muscle nicotinic receptor. Neurosci Lett. 2006 Jun 19;401(1-2):20-4. doi: 10.1016/j.neulet.2006.02.065. Epub 2006 Mar 13. PMID: 16530961. 3. Kenny JD, Chemali JJ, Cotten JF, Van Dort CJ, Kim SE, Ba D, Taylor NE, Brown EN, Solt K. Physostigmine and Methylphenidate Induce Distinct Arousal States During Isoflurane General Anesthesia in Rats. Anesth Analg. 2016 Nov;123(5):1210-1219. doi: 10.1213/ANE.0000000000001234. PMID: 26991753; PMCID: PMC5026857. 4. Dong H, Csernansky CA, Martin MV, Bertchume A, Vallera D, Csernansky JG. Acetylcholinesterase inhibitors ameliorate behavioral deficits in the Tg2576 mouse model of Alzheimer's disease. Psychopharmacology (Berl). 2005 Aug;181(1):145-52. doi: 10.1007/s00213-005-2230-6. Epub 2005 Oct 15. PMID: 15778881; PMCID: PMC1361685.
In vitro protocol:
1. Herkert NM, Schulz S, Wille T, Thiermann H, Hatz RA, Worek F. Pre- and post-treatment effect of physostigmine on soman-inhibited human erythrocyte and muscle acetylcholinesterase in vitro. Toxicol Appl Pharmacol. 2011 May 15;253(1):7-13. doi: 10.1016/j.taap.2011.03.005. Epub 2011 Mar 11. PMID: 21402092. 2. Svobodová L, Krůsek J, Hendrych T, Vyskocil F. Physostigmine modulation of acetylcholine currents in COS cells transfected with mouse muscle nicotinic receptor. Neurosci Lett. 2006 Jun 19;401(1-2):20-4. doi: 10.1016/j.neulet.2006.02.065. Epub 2006 Mar 13. PMID: 16530961.
In vivo protocol:
1. Kenny JD, Chemali JJ, Cotten JF, Van Dort CJ, Kim SE, Ba D, Taylor NE, Brown EN, Solt K. Physostigmine and Methylphenidate Induce Distinct Arousal States During Isoflurane General Anesthesia in Rats. Anesth Analg. 2016 Nov;123(5):1210-1219. doi: 10.1213/ANE.0000000000001234. PMID: 26991753; PMCID: PMC5026857. 2. Dong H, Csernansky CA, Martin MV, Bertchume A, Vallera D, Csernansky JG. Acetylcholinesterase inhibitors ameliorate behavioral deficits in the Tg2576 mouse model of Alzheimer's disease. Psychopharmacology (Berl). 2005 Aug;181(1):145-52. doi: 10.1007/s00213-005-2230-6. Epub 2005 Oct 15. PMID: 15778881; PMCID: PMC1361685.
1: Ferreira J, Tkacz K, Turkiewicz IP, Santos I, Camoesas E Silva M, Lima A, Sousa I. Exploring the Bioactive Properties and Therapeutic Benefits of Pear Pomace. Antioxidants (Basel). 2024 Jun 28;13(7):784. doi: 10.3390/antiox13070784. PMID: 39061853; PMCID: PMC11273397. 2: Yakey B, Vohra V, Martin A, King AM. Treatment of pediatric antimuscarinic delirium with oral rivastigmine. Oxf Med Case Reports. 2023 Sep 25;2023(9):omad096. doi: 10.1093/omcr/omad096. PMID: 37771682; PMCID: PMC10530290. 3: Pinder N, Zimmermann JB, Gastine S, Würthwein G, Hempel G, Bruckner T, Hoppe- Tichy T, Weigand MA, Swoboda S. Continuous infusion of physostigmine in patients with perioperative septic shock: A pharmacokinetic/pharmacodynamic study with population pharmacokinetic modeling. Biomed Pharmacother. 2019 Oct;118:109318. doi: 10.1016/j.biopha.2019.109318. Epub 2019 Aug 6. PMID: 31398669. 4: Pinder N, Bruckner T, Lehmann M, Motsch J, Brenner T, Larmann J, Knebel P, Hoppe-Tichy T, Swoboda S, Weigand MA, Hofer S, Zimmermann JB. Effect of physostigmine on recovery from septic shock following intra-abdominal infection - Results from a randomized, double-blind, placebo-controlled, monocentric pilot trial (Anticholium® per Se). J Crit Care. 2019 Aug;52:126-135. doi: 10.1016/j.jcrc.2019.04.012. Epub 2019 Apr 9. PMID: 31035187. 5: Dhingra D, Soni K. Behavioral and biochemical evidences for nootropic activity of boldine in young and aged mice. Biomed Pharmacother. 2018 Jan;97:895-904. doi: 10.1016/j.biopha.2017.11.011. Epub 2017 Nov 7. PMID: 29136766. 6: Zimmermann JB, Pinder N, Bruckner T, Lehmann M, Motsch J, Brenner T, Hoppe- Tichy T, Swoboda S, Weigand MA, Hofer S. Adjunctive use of physostigmine salicylate (Anticholium®) in perioperative sepsis and septic shock: study protocol for a randomized, double-blind, placebo-controlled, monocentric trial (Anticholium® per Se). Trials. 2017 Nov 10;18(1):530. doi: 10.1186/s13063-017-2231-x. PMID: 29126416; PMCID: PMC5681758. 7: Santillo MF, Liu Y. A fluorescence assay for measuring acetylcholinesterase activity in rat blood and a human neuroblastoma cell line (SH-SY5Y). J Pharmacol Toxicol Methods. 2015 Nov-Dec;76:15-22. doi: 10.1016/j.vascn.2015.07.002. Epub 2015 Jul 9. PMID: 26165232. 8: Ohta R, Takagi A, Ohmukai H, Marumo H, Ono A, Matsushima Y, Inoue T, Ono H, Kanno J. Ovariectomized mouse uterotrophic assay of 36 chemicals. J Toxicol Sci. 2012;37(5):879-89. doi: 10.2131/jts.37.879. PMID: 23037998. 9: Yousefi B, Nasehi M, Khakpai F, Zarrindast MR. Possible interaction of cholinergic and GABAergic systems between MS and CA1 upon memory acquisition in rats. Behav Brain Res. 2012 Dec 1;235(2):231-43. doi: 10.1016/j.bbr.2012.08.006. Epub 2012 Aug 13. PMID: 22909986. 10: Meloun M, Ferenčíková Z, Javůrek M. Reliability of dissociation constants and resolution capability of SQUAD(84) and SPECFIT/32 in the regression of multiwavelength spectrophotometric pH-titration data. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Feb;86:305-14. doi: 10.1016/j.saa.2011.10.041. Epub 2011 Oct 20. PMID: 22078078. 11: Bolourchian N, Hadidi N, Foroutan SM, Shafaghi B. Development and optimization of a sublingual tablet formulation for physostigmine salicylate. Acta Pharm. 2009 Sep;59(3):301-12. doi: 10.2478/v10007-009-0028-5. PMID: 19819826. 12: Manire CA, Byrd L, Rhinehart HL, Cunningham-Smith P, Smith DR. Subacute atropine toxicity in a pygmy sperm whale, Kogia breviceps. J Zoo Wildl Med. 2002 Mar;33(1):66-72. doi: 10.1638/1042-7260(2002)033[0066:SATIAP]2.0.CO;2. PMID: 12216796. 13: Hoffman RJ, Nelson LS, Hoffman RS. Use of ferric chloride to identify salicylate-containing poisons. J Toxicol Clin Toxicol. 2002;40(5):547-9. doi: 10.1081/clt-120014643. PMID: 12215048. 14: Tekol Y, Eminel S. Combined use of tertiary amine parasympathomimetics with a quaternary amine parasympatholitic--a new perspective to use parasympathomimetic drugs for systemic analgesia. Pharmazie. 2002 Jul;57(7):485-6. PMID: 12168532. 15: Meshulam Y, Cohen G, Chapman S, Alkalai D, Levy A. Prophylaxis against organophosphate poisoning by sustained release of scopolamine and physostigmine. J Appl Toxicol. 2001 Dec;21 Suppl 1:S75-8. doi: 10.1002/jat.815. PMID: 11920924. 16: Matschiner F, Berghaus A, Kober A, Henschel H, Kluge S. Anticholinerges Syndrom nach postoperativer Dimenhydrinatgabe [Anticholinergic syndrome after postoperative dimenhydrinate administration]. HNO. 2001 Dec;49(12):1026-8. German. doi: 10.1007/s001060170007. PMID: 11793918. 17: Coelho F, Birks J. Physostigmine for Alzheimer's disease. Cochrane Database Syst Rev. 2001;2001(2):CD001499. doi: 10.1002/14651858.CD001499. PMID: 11405996; PMCID: PMC8078195. 18: Parisi P, Francia A. A female with central anticholinergic syndrome responsive to neostigmine. Pediatr Neurol. 2000 Aug;23(2):185-7. doi: 10.1016/s0887-8994(00)00165-x. PMID: 11020649. 19: Kuhl DE, Minoshima S, Frey KA, Foster NL, Kilbourn MR, Koeppe RA. Limited donepezil inhibition of acetylcholinesterase measured with positron emission tomography in living Alzheimer cerebral cortex. Ann Neurol. 2000 Sep;48(3):391-5. PMID: 10976649. 20: van Dyck CH, Newhouse P, Falk WE, Mattes JA. Extended-release physostigmine in Alzheimer disease: a multicenter, double-blind, 12-week study with dose enrichment. Physostigmine Study Group. Arch Gen Psychiatry. 2000 Feb;57(2):157-64. doi: 10.1001/archpsyc.57.2.157. PMID: 10665618.