Neostigmine methylsulfate | CAS#51-60-5 | 59-99-4

MedKoo Cat#: 318358 | Name: Neostigmine methylsulfate

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Description:

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

Neostigmine is a parasympathomimetic compound that acts as a reversible acetylcholinesterase inhibitor. Given that it is a quaternary amine (unlike physostigmine, which is a tertiary amine), it penetrates the central nervous system poorly and has lower propensity to cause side effects there.

Chemical Structure

Neostigmine methylsulfate

CAS#51-60-5 (methylsulfate)

Theoretical Analysis

MedKoo Cat#: 318358

Name: Neostigmine methylsulfate

CAS#: 51-60-5 (methylsulfate)

Chemical Formula: C13H22N2O6S

Exact Mass: 223.1441

Molecular Weight: 334.39

Elemental Analysis: C, 46.70; H, 6.63; N, 8.38; O, 28.71; S, 9.59

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 450.00	2 Weeks
5g	USD 750.00	2 Weeks
10g	USD 1,250.00	2 Weeks

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Related CAS #

59-99-4 (cation) 114-80-7 (bromide) 51-60-5 (methylsulfate) 1212-37-9 (iodide) 588-17-0 (hydroxide)

Synonym

Neostigmine, Prostigmin, Vagostigmin, Polstigmine; Neostigmine methylsulfate

IUPAC/Chemical Name

3-((dimethylcarbamoyl)oxy)-N,N,N-trimethylbenzenaminium methyl sulfate

InChi Key

OSZNNLWOYWAHSS-UHFFFAOYSA-M

InChi Code

InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1

SMILES Code

C[N+](C)(C1=CC=CC(OC(N(C)C)=O)=C1)C.O=S(OC)([O-])=O

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, not in water

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:

Neostigmine methyl sulfate is a reversible inhibitor of acetylcholinesterase, can not cross the blood-brain barrier.

In vitro activity:

In this study, the cytotoxicity, genotoxicity and apoptotic effects of Sugammadex and Neostigmine on HEK-293 cells were analyzed with using the MTT, Comet Assay and Flow Cytometric Annexin-V methods, respectively. The results demonstrate that Neostigmine at 50, 100, 250, and 500 µg/mL is more cytotoxic than equivalent dosages of Sugammadex. Neostigmine at 500 and 1000 µg/mL was found to be more genotoxic, and Neostigmine at 500 µg/mL had a statistically higher risk of causing apoptosis and necrosis than Sugammadex (p<0.05). Reference: Cell Mol Biol (Noisy-le-grand). 2018 Oct 30;64(13):74-78. https://pubmed.ncbi.nlm.nih.gov/30403599/

In vivo activity:

In this sense, the aim of this study is to investigate the effects of treatment with neostigmine, known for the ability to control lung inflammation, on oxidative stress in the cerebral cortex of asthmatic mice. Female BALB/cJ mice were submitted to asthma model induced by ovalbumin (OVA). Control group received only Dulbecco's phosphate-buffered saline (DPBS). To evaluate neostigmine effects, mice received 80 μg/kg of neostigmine intraperitoneally 30 min after each OVA challenge. The results revealed for the first time that treatment with neostigmine (an acetylcholinesterase inhibitor that no crosses the BBB) was able to revert ROS production and change anti-oxidant enzyme catalase in the cerebral cortex in asthmatic mice. Reference: Metab Brain Dis. 2020 Jun;35(5):765-774. https://pubmed.ncbi.nlm.nih.gov/32189127/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	299.05
	Water	100.0	299.05

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 334.39 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.

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. Büyükfırat E, Koyuncu İ, Karahan MA, Binici O, Altay N, Kirmit A, Gönel A. Comparison of the cytotoxic, genotoxic and apoptotic effects of Sugammadex and Neostigmine on human embryonic renal cell (HEK-293). Cell Mol Biol (Noisy-le-grand). 2018 Oct 30;64(13):74-78. PMID: 30403599. 2. Mustafa S, Ismael HN. Reactivity of diabetic urinary bladder to the cholinesterase inhibitor neostigmine. Urology. 2014 Dec;84(6):1549.e1-5. doi: 10.1016/j.urology.2014.08.019. Epub 2014 Oct 14. PMID: 25440827. 3. Antunes GL, Silveira JS, Kaiber DB, Luft C, Dos Santos TM, Marques EP, Ferreira FS, Schmitz F, de Souza Wyse AT, Stein RT, Pitrez PM, da Cunha AA. Neostigmine treatment induces neuroprotection against oxidative stress in cerebral cortex of asthmatic mice. Metab Brain Dis. 2020 Jun;35(5):765-774. doi: 10.1007/s11011-020-00558-7. Epub 2020 Mar 18. PMID: 32189127. 4. Fogaça MV, Fedoce AG, Ferreira-Junior NC, Guimarães FS, Resstel LB. Involvement of M1 and CB₁ receptors in the anxiogenic-like effects induced by neostigmine injected into the rat prelimbic medial prefrontal cortex. Psychopharmacology (Berl). 2016 Apr;233(8):1377-85. doi: 10.1007/s00213-016-4228-7. Epub 2016 Feb 13. PMID: 26873081.

In vitro protocol:

In vivo protocol:

1. Antunes GL, Silveira JS, Kaiber DB, Luft C, Dos Santos TM, Marques EP, Ferreira FS, Schmitz F, de Souza Wyse AT, Stein RT, Pitrez PM, da Cunha AA. Neostigmine treatment induces neuroprotection against oxidative stress in cerebral cortex of asthmatic mice. Metab Brain Dis. 2020 Jun;35(5):765-774. doi: 10.1007/s11011-020-00558-7. Epub 2020 Mar 18. PMID: 32189127. 2. Fogaça MV, Fedoce AG, Ferreira-Junior NC, Guimarães FS, Resstel LB. Involvement of M1 and CB₁ receptors in the anxiogenic-like effects induced by neostigmine injected into the rat prelimbic medial prefrontal cortex. Psychopharmacology (Berl). 2016 Apr;233(8):1377-85. doi: 10.1007/s00213-016-4228-7. Epub 2016 Feb 13. PMID: 26873081.

1: Abad-Gurumeta A, Ripollés-Melchor J, Casans-Francés R, Espinosa A, Martínez-Hurtado E, Fernández-Pérez C, Ramírez JM, López-Timoneda F, Calvo-Vecino JM; Evidence Anaesthesia Review Group. A systematic review of sugammadex vs neostigmine for reversal of neuromuscular blockade. Anaesthesia. 2015 Dec;70(12):1441-52. doi: 10.1111/anae.13277. Review. PubMed PMID: 26558858. 2: Lauretti GR. The evolution of spinal/epidural neostigmine in clinical application: Thoughts after two decades. Saudi J Anaesth. 2015 Jan;9(1):71-81. doi: 10.4103/1658-354X.146319. Review. PubMed PMID: 25558203; PubMed Central PMCID: PMC4279354. 3: Liu SH, Tseng CY, Lin CC. Is neostigmine effective in severe pufferfish-associated tetrodotoxin poisoning? Clin Toxicol (Phila). 2015 Jan;53(1):13-21. doi: 10.3109/15563650.2014.980581. Epub 2014 Nov 20. Review. PubMed PMID: 25410493. 4: Valle RG, Godoy FL. Neostigmine for acute colonic pseudo-obstruction: A meta-analysis. Ann Med Surg (Lond). 2014 Jun 19;3(3):60-4. doi: 10.1016/j.amsu.2014.04.002. eCollection 2014 Sep. Review. PubMed PMID: 25568788; PubMed Central PMCID: PMC4284455. 5: Yang L, Yang D, Li Q, Zuo Y, Lu D. Neostigmine for reversal of neuromuscular block in paediatric patients. Cochrane Database Syst Rev. 2014 May 5;5:CD010110. doi: 10.1002/14651858.CD010110.pub2. Review. PubMed PMID: 24793636. 6: Elsner JL, Smith JM, Ensor CR. Intravenous neostigmine for postoperative acute colonic pseudo-obstruction. Ann Pharmacother. 2012 Mar;46(3):430-5. doi: 10.1345/aph.1Q515. Epub 2012 Feb 28. Review. PubMed PMID: 22388328. 7: Kayani B, Spalding DR, Jiao LR, Habib NA, Zacharakis E. Does neostigmine improve time to resolution of symptoms in acute colonic pseudo-obstruction? Int J Surg. 2012;10(9):453-7. doi: 10.1016/j.ijsu.2012.08.008. Epub 2012 Sep 14. Review. PubMed PMID: 22985773. 8: Paton F, Paulden M, Chambers D, Heirs M, Duffy S, Hunter JM, Sculpher M, Woolacott N. Sugammadex compared with neostigmine/glycopyrrolate for routine reversal of neuromuscular block: a systematic review and economic evaluation. Br J Anaesth. 2010 Nov;105(5):558-67. doi: 10.1093/bja/aeq269. Epub 2010 Oct 8. Review. PubMed PMID: 20935005; PubMed Central PMCID: PMC2955536. 9: Mizikov VM, Stamov VI, Deshko IuV, Ialich AIu. [Problem of neuromuscular block reversion: neostigmine and sugammadex]. Anesteziol Reanimatol. 2010 Mar-Apr;(2):40-3. Review. Russian. PubMed PMID: 20524330. 10: Lee C, Katz RL. Clinical implications of new neuromuscular concepts and agents: so long, neostigmine! So long, sux! J Crit Care. 2009 Mar;24(1):43-9. doi: 10.1016/j.jcrc.2008.08.009. Epub 2009 Jan 17. Review. PubMed PMID: 19272538. 11: McNamara R, Mihalakis MJ. Acute colonic pseudo-obstruction: rapid correction with neostigmine in the emergency department. J Emerg Med. 2008 Aug;35(2):167-70. doi: 10.1016/j.jemermed.2007.06.043. Epub 2008 Feb 1. Review. PubMed PMID: 18242923. 12: Ho KM, Ismail H, Lee KC, Branch R. Use of intrathecal neostigmine as an adjunct to other spinal medications in perioperative and peripartum analgesia: a meta-analysis. Anaesth Intensive Care. 2005 Feb;33(1):41-53. Review. PubMed PMID: 15957690. 13: Maeda N, Murai M, Nakazawa A, Suzuki O, Mizuno Y, Yamamoto Y, Shimizu K, Hibi T. [A case of chronic colonic pseudo-obstruction due to amyloidosis successfully treated with neostigmine]. Nihon Shokakibyo Gakkai Zasshi. 2004 Jun;101(6):609-15. Review. Japanese. PubMed PMID: 15233262. 14: Habib AS, Gan TJ. Use of neostigmine in the management of acute postoperative pain and labour pain: a review. CNS Drugs. 2006;20(10):821-39. Review. PubMed PMID: 16999453. 15: Roelants F. The use of neuraxial adjuvant drugs (neostigmine, clonidine) in obstetrics. Curr Opin Anaesthesiol. 2006 Jun;19(3):233-7. Review. PubMed PMID: 16735803. 16: Eisenach JC. Three novel spinal analgesics: clonidine, neostigmine, amitriptyline. Reg Anesth. 1996 Nov-Dec;21(6 Suppl):81-3. Review. PubMed PMID: 8956428. 17: Hazama M, Nakano M, Shinozaki M, Fujisawa M, Okamoto Y, Ren KZ, Oka N, Hamaguchi T, Okada H, Matsumoto O, et al. [A case of a complete paraplegic fathering a girl following artificial insemination after an intrathecal neostigmine injection]. Hinyokika Kiyo. 1988 Jun;34(6):1047-50. Review. Japanese. PubMed PMID: 3066212.

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Neostigmine

MedKoo CAT#: 596343

CAS#: 59-99-4