Synonym
Hirsuteine; 3-Epicorynantheine; 3Epicorynantheine; 3 Epicorynantheine
IUPAC/Chemical Name
methyl (E)-3-methoxy-2-((2S,3R,12bR)-3-vinyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)acrylate
InChi Key
TZUGIFAYWNNSAO-AZQGJTAVSA-N
InChi Code
InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13-14,17,20,23H,1,9-12H2,2-3H3/b18-13+/t14-,17-,20+/m0/s1
SMILES Code
COC(/C([C@H]1C[C@@]2(C3=C(C4=CC=CC=C4N3)CCN2C[C@@H]1C=C)[H])=C/OC)=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
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
366.46
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: Zhou Q, Ma J, Chen L. Tissue Distribution of Hirsutine and Hirsuteine in Mice by Ultrahigh-Performance Liquid Chromatography-Mass Spectrometry. J Anal Methods Chem. 2020 Apr 21;2020:7204315. doi: 10.1155/2020/7204315. PMID: 32399311; PMCID: PMC7201850.
2: Wang M, Guo J, Wang Z, Zhang G, Yu H, Chang R, Chen A. Simultaneous separation and determination of hirsutine and hirsuteine by cyclodextrin- modified micellar electrokinetic capillary chromatography. Phytochem Anal. 2020 Jan;31(1):112-118. doi: 10.1002/pca.2871. Epub 2019 Jul 21. PMID: 31328320.
3: Watano T, Nakazawa K, Obama T, Mori M, Inoue K, Fujimori K, Takanaka A. Non- competitive antagonism by hirsuteine of nicotinic receptor-mediated dopamine release from rat pheochromocytoma cells. Jpn J Pharmacol. 1993 Apr;61(4):351-6. doi: 10.1254/jjp.61.351. PMID: 8320880.
4: Nakazawa T, Banba K, Hata K, Nihei Y, Hoshikawa A, Ohsawa K. Metabolites of hirsuteine and hirsutine, the major indole alkaloids of Uncaria rhynchophylla, in rats. Biol Pharm Bull. 2006 Aug;29(8):1671-7. doi: 10.1248/bpb.29.1671. PMID: 16880624.
5: Gao S, Guo T, Luo S, Zhang Y, Ren Z, Lang X, Hu G, Zuo D, Jia W, Kong D, Yu H, Qiu Y. Growth Inhibitory and Pro-Apoptotic Effects of Hirsuteine in Chronic Myeloid Leukemia Cells through Targeting Sphingosine Kinase 1. Biomol Ther (Seoul). 2022 Jun 15. doi: 10.4062/biomolther.2022.023. Epub ahead of print. PMID: 35702821.
