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
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
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.
| 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: 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.
