Rivastigmine Free Base | CAS# 123441-03-2 (free base) | Cholinesterase Inhibitor

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

MedKoo CAT#: 414009

CAS#: 123441-03-2 (free base)

Description: Rivastigmine, also known as S-Rivastigmine, is an orally active and potent cholinesterase (ChE) inhibitor. Rivastigmine is a parasympathomimetic or cholinergic agent used for the research of mild to moderate dementia, particularly Alzheimer's and dementia due to Parkinson's disease.

Chemical Structure

Rivastigmine free base

CAS# 123441-03-2 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 414009
Name: Rivastigmine free base
CAS#: 123441-03-2 (free base)
Chemical Formula: C14H22N2O2
Exact Mass: 250.17
Molecular Weight: 250.340
Elemental Analysis: C, 67.17; H, 8.86; N, 11.19; O, 12.78

Price and Availability

Size	Price	Availability
1g	USD 250	2 Weeks
5g	USD 650	2 Weeks
10g	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 123441-03-2 (free base) 129101-54-8 (tartrate)

Synonym: Rivastigmine Free Base; ENA713; ENA 713; ENA-713; S-Rivastigmine

IUPAC/Chemical Name: (S)-3-(1-(Dimethylamino)ethyl)phenyl ethylmethylcarbamate

InChi Key: XSVMFMHYUFZWBK-NSHDSACASA-N

InChi Code: InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1

SMILES Code: O=C(OC1=CC=CC([C@@H](N(C)C)C)=C1)N(CC)C

Appearance: Liquid

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

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Product Data:

Product Data

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Biological target:	Rivastigmine inhibits butyrylcholinesterase (BChE) and acetylcholinesteras (AChE) with IC50s of 0.037 μM , 4.15 μM, respectively. Rivastigmine can pass the blood brain barrier.
In vitro activity:	The results from this study show that rivastigmine affords neuroprotection through a mechanism that is likely unrelated to AChE inhibition. For rivastigmine, the exact mechanism is unknown. PI3K-Akt blocker 2-(4-morpholinyl)-8-phenyl-1(4H)-benzopyran-4-one hydrochloride (LY294002) did not reverse the effects of rivastigmine. Reference: J Pharmacol Exp Ther. 2005 Dec;315(3):1346-53. https://pubmed.ncbi.nlm.nih.gov/16144975/
In vivo activity:	In male rats, rivastigmine administration alleviated biochemical and histological parameters and partially ameliorated Botulinum toxin (Botox)-induced impairments. Rivastigmine could be a suitable protective approach for side effects of Botox in the hippocampus.The hippocampal cholinergic system plays a significant role in memory and learning that could be affected by Botox. Reference: Neurotoxicology. 2023 Jul 26;98:29-38. https://pubmed.ncbi.nlm.nih.gov/37507053/

Preparing Stock Solutions

The following data is based on the product molecular weight 250.34 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. Terada K, Migita K, Matsushima Y, Sugimoto Y, Kamei C, Matsumoto T, Mori M, Matsunaga K, Takata J, Karube Y. Cholinesterase inhibitor rivastigmine enhances nerve growth factor-induced neurite outgrowth in PC12 cells via sigma-1 and sigma-2 receptors. PLoS One. 2018 Dec 17;13(12):e0209250. doi: 10.1371/journal.pone.0209250. PMID: 30557385; PMCID: PMC6296549. 2. Arias E, Gallego-Sandín S, Villarroya M, García AG, López MG. Unequal neuroprotection afforded by the acetylcholinesterase inhibitors galantamine, donepezil, and rivastigmine in SH-SY5Y neuroblastoma cells: role of nicotinic receptors. J Pharmacol Exp Ther. 2005 Dec;315(3):1346-53. doi: 10.1124/jpet.105.090365. Epub 2005 Sep 6. PMID: 16144975. 3. Mehri K, Oskuye ZZ, Nassireslami E, Karami E, Parvizi MR. Rivastigmine ameliorates botulinum-induced hippocampal damage and spatial memory impairment in male rats. Neurotoxicology. 2023 Jul 26;98:29-38. doi: 10.1016/j.neuro.2023.07.004. Epub ahead of print. PMID: 37507053. 4. Gupta P, Tiwari S, Singh A, Pal A, Mishra A, Singh S. Rivastigmine attenuates the Alzheimer's disease related protein degradation and apoptotic neuronal death signalling. Biochem J. 2021 Apr 16;478(7):1435-1451. doi: 10.1042/BCJ20200754. Erratum in: Biochem J. 2022 Jun 17;479(11):1147. PMID: 33660768.
In vitro protocol:	1. Terada K, Migita K, Matsushima Y, Sugimoto Y, Kamei C, Matsumoto T, Mori M, Matsunaga K, Takata J, Karube Y. Cholinesterase inhibitor rivastigmine enhances nerve growth factor-induced neurite outgrowth in PC12 cells via sigma-1 and sigma-2 receptors. PLoS One. 2018 Dec 17;13(12):e0209250. doi: 10.1371/journal.pone.0209250. PMID: 30557385; PMCID: PMC6296549. 2. Arias E, Gallego-Sandín S, Villarroya M, García AG, López MG. Unequal neuroprotection afforded by the acetylcholinesterase inhibitors galantamine, donepezil, and rivastigmine in SH-SY5Y neuroblastoma cells: role of nicotinic receptors. J Pharmacol Exp Ther. 2005 Dec;315(3):1346-53. doi: 10.1124/jpet.105.090365. Epub 2005 Sep 6. PMID: 16144975.
In vivo protocol:	1. Mehri K, Oskuye ZZ, Nassireslami E, Karami E, Parvizi MR. Rivastigmine ameliorates botulinum-induced hippocampal damage and spatial memory impairment in male rats. Neurotoxicology. 2023 Jul 26;98:29-38. doi: 10.1016/j.neuro.2023.07.004. Epub ahead of print. PMID: 37507053. 2. Gupta P, Tiwari S, Singh A, Pal A, Mishra A, Singh S. Rivastigmine attenuates the Alzheimer's disease related protein degradation and apoptotic neuronal death signalling. Biochem J. 2021 Apr 16;478(7):1435-1451. doi: 10.1042/BCJ20200754. Erratum in: Biochem J. 2022 Jun 17;479(11):1147. PMID: 33660768.

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1: Birks JS, Grimley Evans J. Rivastigmine for Alzheimer's disease. Cochrane Database Syst Rev. 2015 Apr 10;(4):CD001191. doi: 10.1002/14651858.CD001191.pub3. PMID: 25858345.

2: Kandiah N, Pai MC, Senanarong V, Looi I, Ampil E, Park KW, Karanam AK, Christopher S. Rivastigmine: the advantages of dual inhibition of acetylcholinesterase and butyrylcholinesterase and its role in subcortical vascular dementia and Parkinson's disease dementia. Clin Interv Aging. 2017 Apr 18;12:697-707. doi: 10.2147/CIA.S129145. PMID: 28458525; PMCID: PMC5402908.

3: Espay AJ, Marsili L, Mahajan A, Sturchio A, Pathan R, Pilotto A, Elango DS, Pezous N, Masellis M, Gomez-Mancilla B. Rivastigmine in Parkinson's Disease Dementia with Orthostatic Hypotension. Ann Neurol. 2021 Jan;89(1):91-98. doi: 10.1002/ana.25923. Epub 2020 Oct 20. PMID: 33016374.

4: Hansen RA, Gartlehner G, Webb AP, Morgan LC, Moore CG, Jonas DE. Efficacy and safety of donepezil, galantamine, and rivastigmine for the treatment of Alzheimer's disease: a systematic review and meta-analysis. Clin Interv Aging. 2008;3(2):211-25. PMID: 18686744; PMCID: PMC2546466.

5: Sang Z, Wang K, Shi J, Cheng X, Zhu G, Wei R, Ma Q, Yu L, Zhao Y, Tan Z, Liu W. Apigenin-rivastigmine hybrids as multi-target-directed liagnds for the treatment of Alzheimer's disease. Eur J Med Chem. 2020 Feb 1;187:111958. doi: 10.1016/j.ejmech.2019.111958. Epub 2019 Dec 16. PMID: 31865014.

6: Henderson EJ, Lord SR, Brodie MA, Gaunt DM, Lawrence AD, Close JC, Whone AL, Ben-Shlomo Y. Rivastigmine for gait stability in patients with Parkinson's disease (ReSPonD): a randomised, double-blind, placebo-controlled, phase 2 trial. Lancet Neurol. 2016 Mar;15(3):249-58. doi: 10.1016/S1474-4422(15)00389-0. Epub 2016 Jan 13. PMID: 26795874.

7: Monji A. [Rivastigmine]. Nihon Rinsho. 2011 Dec;69 Suppl 10 Pt 2:36-40. Japanese. PMID: 22755152.

8: Chou PS, Jhang KM, Huang LC, Wang WF, Yang YH. Skinfold thickness for rivastigmine patch application in Alzheimer's disease. Psychopharmacology (Berl). 2019 Apr;236(4):1255-1260. doi: 10.1007/s00213-018-5135-x. Epub 2019 Jan 15. PMID: 30645680.

9: Siddiqui MA, Wagstaff AJ. Rivastigmine: in Parkinson's disease dementia. CNS Drugs. 2006;20(9):739-47; discussion 748-50. doi: 10.2165/00023210-200620090-00003. PMID: 16953649.

10: Grossberg GT, Sadowsky C, Olin JT. Rivastigmine transdermal system for the treatment of mild to moderate Alzheimer's disease. Int J Clin Pract. 2010 Apr;64(5):651-60. doi: 10.1111/j.1742-1241.2009.02330.x. Epub 2010 Jan 19. PMID: 20102418.

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