Bisnorcymserine

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MedKoo CAT#: 527704

CAS#: 219920-81-7

Description: Bisnorcymserine, also known as N1-N8-Bisnorcymserine, is a butyrylcholinesterase inhibitor potentially for the treatment of Alzheimer's disease. The leaving group, bisnoreseroline, interacts in a non-covalent way with Ser(200) and His(440), disrupting the existing interactions within the catalytic triad, and it stacks with Trp(84) at the bottom of the gorge, giving rise to an unprecedented hydrogen-bonding contact. These interactions point to a dominant reversible inhibition mechanism attributable to the leaving group, bisnoreseroline, as revealed by kinetic analysis.

Chemical Structure

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Bisnorcymserine
CAS# 219920-81-7
Instruction

Theoretical Analysis

MedKoo Cat#: 527704
Name: Bisnorcymserine
CAS#: 219920-81-7
Chemical Formula: C21H25N3O2
Exact Mass: 351.19
Molecular Weight: 351.450
Elemental Analysis: C, 71.77; H, 7.17; N, 11.96; O, 9.10

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Bisnorcymserine; N1-N8-Bisnorcymserine; N1 N8 Bisnorcymserine; N1N8Bisnorcymserine

IUPAC/Chemical Name: (3aS,8aR)-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl (4-isopropylphenyl)carbamate

InChi Key: ZIGIADNCAWZUAB-CTNGQTDRSA-N

InChi Code: InChI=1S/C21H25N3O2/c1-13(2)14-4-6-15(7-5-14)23-20(25)26-16-8-9-18-17(12-16)21(3)10-11-22-19(21)24-18/h4-9,12-13,19,22,24H,10-11H2,1-3H3,(H,23,25)/t19-,21+/m1/s1

SMILES Code: O=C(OC1=CC2=C(N[C@]3([H])[C@@]2(C)CCN3)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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 351.45 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:
In vitro protocol:
In vivo protocol:

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1: Bartolucci C, Stojan J, Yu QS, Greig NH, Lamba D. Kinetics of Torpedo californica acetylcholinesterase inhibition by bisnorcymserine and crystal structure of the complex with its leaving group. Biochem J. 2012 Jun 1;444(2):269-77. doi: 10.1042/BJ20111675. PubMed PMID: 22390827; PubMed Central PMCID: PMC4979005.

2: Kamal MA, Klein P, Yu QS, Tweedie D, Li Y, Holloway HW, Greig NH. Kinetics of human serum butyrylcholinesterase and its inhibition by a novel experimental Alzheimer therapeutic, bisnorcymserine. J Alzheimers Dis. 2006 Sep;10(1):43-51. PubMed PMID: 16988481.

3: Macdonald IR, Rockwood K, Martin E, Darvesh S. Cholinesterase inhibition in Alzheimer's disease: is specificity the answer? J Alzheimers Dis. 2014;42(2):379-84. doi: 10.3233/JAD-140219. Review. PubMed PMID: 24898642.

4: 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. PubMed PMID: 27712576.

5: 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. PubMed PMID: 24059300.