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MedKoo Cat#: 413427 | Name: Cymserine

Description:

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

Cymserine is a drug related to physostigmine, which acts as a reversible cholinesterase inhibitor, with moderate selectivity for the plasma cholinesterase enzyme butyrylcholinesterase, and relatively weaker inhibition of the better-known acetylcholinesterase enzyme.

Chemical Structure

Cymserine
Cymserine
CAS#145209-39-8

Theoretical Analysis

MedKoo Cat#: 413427

Name: Cymserine

CAS#: 145209-39-8

Chemical Formula: C23H29N3O2

Exact Mass: 379.2260

Molecular Weight: 379.50

Elemental Analysis: C, 72.79; H, 7.70; N, 11.07; O, 8.43

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Cymserine
IUPAC/Chemical Name
Carbamic acid, N-(4-(1-methylethyl)phenyl)-, (3aS,8aR)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-yl ester
InChi Key
NKJRRVBTMYRXRB-GGAORHGYSA-N
InChi Code
InChI=1S/C23H29N3O2/c1-15(2)16-6-8-17(9-7-16)24-22(27)28-18-10-11-20-19(14-18)23(3)12-13-25(4)21(23)26(20)5/h6-11,14-15,21H,12-13H2,1-5H3,(H,24,27)/t21-,23+/m1/s1
SMILES Code
O=C(OC1=CC2=C(N(C)[C@]3([H])[C@@]2(C)CCN3C)C=C1)NC4=CC=C(C(C)C)C=C4
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 379.50 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
1: Kamal MA, Qu X, Yu QS, Tweedie D, Holloway HW, Li Y, Tan Y, Greig NH. Tetrahydrofurobenzofuran cymserine, a potent butyrylcholinesterase inhibitor and experimental Alzheimer drug candidate, enzyme kinetic analysis. J Neural Transm (Vienna). 2008 Jun;115(6):889-98. doi: 10.1007/s00702-008-0022-y. Epub 2008 Jan 31. PMID: 18235987; PMCID: PMC5193500. 2: ul Ain Q, Greig NH, Nawaz MS, Rashid S, Kamal MA. Exploring N(1)-p-fluorobenzyl-cymserine as an inhibitor of 5-lipoxygenase as a candidate for type 2 diabetes and neurodegenerative disorder treatment. CNS Neurol Disord Drug Targets. 2014 Mar;13(2):197-202. doi: 10.2174/18715273113126660136. PMID: 24059322; PMCID: PMC4807432. 3: Batool S, Nawaz MS, Greig NH, Rehan M, Kamal MA. Molecular interaction study of N1-p-fluorobenzyl-cymserine with TNF-α , p38 kinase and JNK kinase. Antiinflamm Antiallergy Agents Med Chem. 2013;12(2):129-35. doi: 10.2174/1871523011312020004. PMID: 23360257; PMCID: PMC4807428. 4: Kamal MA, Al-Jafari AA, Yu QS, Greig NH. Kinetic analysis of the inhibition of human butyrylcholinesterase with cymserine. Biochim Biophys Acta. 2006 Feb;1760(2):200-6. doi: 10.1016/j.bbagen.2005.10.003. Epub 2005 Oct 27. PMID: 16309845. 5: Kamal MA, Klein P, Luo W, Li Y, Holloway HW, Tweedie D, Greig NH. Kinetics of human serum butyrylcholinesterase inhibition by a novel experimental Alzheimer therapeutic, dihydrobenzodioxepine cymserine. Neurochem Res. 2008 May;33(5):745-53. doi: 10.1007/s11064-007-9490-y. Epub 2007 Nov 6. PMID: 17985237; PMCID: PMC5201206. 6: Shaikh S, Ahmad SS, Ansari MA, Shakil S, Rizvi SM, Shakil S, Tabrez S, Akhtar S, Kamal MA. Prediction of comparative inhibition efficiency for a novel natural ligand, galangin against human brain acetylcholinesterase, butyrylcholinesterase and 5-lipoxygenase: a neuroinformatics study. CNS Neurol Disord Drug Targets. 2014 Apr;13(3):452-9. doi: 10.2174/18715273113126660162. PMID: 24059300. 7: Ahmad SS, Akhtar S, Jamal QM, Rizvi SM, Kamal MA, Khan MK, Siddiqui MH. Multiple Targets for the Management of Alzheimer's Disease. CNS Neurol Disord Drug Targets. 2016;15(10):1279-1289. doi: 10.2174/1871527315666161003165855. PMID: 27712576. 8: Greig NH, Utsuki T, Ingram DK, Wang Y, Pepeu G, Scali C, Yu QS, Mamczarz J, Holloway HW, Giordano T, Chen D, Furukawa K, Sambamurti K, Brossi A, Lahiri DK. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent. Proc Natl Acad Sci U S A. 2005 Nov 22;102(47):17213-8. doi: 10.1073/pnas.0508575102. Epub 2005 Nov 7. PMID: 16275899; PMCID: PMC1288010. 9: Košak U, Gobec S. A Simple and Effective Synthesis of 3- and 4-((Phenylcarbamoyl)oxy)benzoic Acids. Acta Chim Slov. 2020 Sep;67(3):940-948. PMID: 33533422. 10: Carmona GN, Schindler CW, Greig NH, Holloway HW, Jufer RA, Cone EJ, Gorelick DA. Intravenous butyrylcholinesterase administration and plasma and brain levels of cocaine and metabolites in rats. Eur J Pharmacol. 2005 Jul 11;517(3):186-90. doi: 10.1016/j.ejphar.2005.05.013. PMID: 15967428.