Rubreserine

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

MedKoo CAT#: 461543

CAS#: 18455-27-1

Description: Rubreserine is a degradation product of physostigmine.

Chemical Structure

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Rubreserine
CAS# 18455-27-1
Instruction

Theoretical Analysis

MedKoo Cat#: 461543
Name: Rubreserine
CAS#: 18455-27-1
Chemical Formula: C13H16N2O2
Exact Mass: 232.12
Molecular Weight: 232.280
Elemental Analysis: C, 67.22; H, 6.94; N, 12.06; O, 13.78

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: Rubreserine;

IUPAC/Chemical Name: (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-5,6-dione

InChi Key: HOQNKCYZDSDWJL-OLZOCXBDSA-N

InChi Code: InChI=1S/C13H16N2O2/c1-13-4-5-14(2)12(13)15(3)9-7-11(17)10(16)6-8(9)13/h6-7,12H,4-5H2,1-3H3/t12-,13+/m1/s1

SMILES Code: O=C1C=C2[C@@]3(C)[C@@](N(C)CC3)([H])N(C)C2=CC1=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

Shelf Life: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 232.28 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: Camara D, Bisanz C, Barette C, Van Daele J, Human E, Barnard B, Van der Straeten D, Stove CP, Lambert WE, Douce R, Maréchal E, Birkholtz LM, Cesbron-Delauw MF, Dumas R, Rébeillé F. Inhibition of p-aminobenzoate and folate syntheses in plants and apicomplexan parasites by natural product rubreserine. J Biol Chem. 2012 Jun 22;287(26):22367-76. doi: 10.1074/jbc.M112.365833. Epub 2012 May 10. PubMed PMID: 22577137; PubMed Central PMCID: PMC3381196.

2: ROBINSON B. THE STRUCTURE OF RUBRESERINE, A DECOMPOSITION PRODUCT OF PHYSOSTIGMINE. J Pharm Pharmacol. 1965 Feb;17:89-91. PubMed PMID: 14293064.

3: Schönenberger B, Jacobson AE, Brossi A, Streaty R, Klee WA, Flippen-Anderson JL, Gilardi R. Comparison of (-)-eseroline with (+)-eseroline and dihydroseco analogues in antinociceptive assays: confirmation of rubreserine structure by X-ray analysis. J Med Chem. 1986 Nov;29(11):2268-73. PubMed PMID: 3023611.

4: Kneczke M. Determination of pilocarpine, physostigmine, its degradation product rubreserine and preservatives by high-performance liquid chromatography. J Chromatogr. 1980 Oct 24;198(4):529-33. PubMed PMID: 7440688.

5: Yu Q, Greig NH, Holloway HW, Brossi A. Syntheses and anticholinesterase activities of (3aS)-N1, N8-bisnorphenserine, (3aS)-N1,N8-bisnorphysostigmine, their antipodal isomers, and other potential metabolites of phenserine. J Med Chem. 1998 Jun 18;41(13):2371-9. PubMed PMID: 9632370.

6: Isaksson K, Kissinger PT. Metabolism of physostigmine in mouse liver microsomal incubations studied by liquid chromatography with dual-electrode amperometric detection. J Chromatogr. 1987 Aug 7;419:165-75. PubMed PMID: 3667775.

7: Chen JL, Yeh MK, Chiang CH. Anaerobic stability of aqueous physostigmine solution. Drug Dev Ind Pharm. 2000 Sep;26(9):1007-11. PubMed PMID: 10914327.