Synonym
Rhynchophylline; Mitrinermine;
IUPAC/Chemical Name
methyl (E)-2-((3R,6'R,7'S,8a'S)-6'-ethyl-2-oxo-2',3',6',7',8',8a'-hexahydro-5'H-spiro[indoline-3,1'-indolizin]-7'-yl)-3-methoxyacrylate
InChi Key
DAXYUDFNWXHGBE-KAXDATADSA-N
InChi Code
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1
SMILES Code
O=C1[C@]2(CCN3[C@H]2C[C@H](/C(C(OC)=O)=C\OC)[C@@H](CC)C3)C4=CC=CC=C4N1
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
Biological target:
Rhynchophylline exibits numerous pharmacological activities including hypotensive, neuroprotective, anticonvulsive, antiepileptic, antiarrhythmic, anticoagulant, antispasmodic, and sedative. Rhynchophylline modulates voltage-gated K+ (Kv) channel slow inactivation in mouse neuroblastoma N2A cells. Rhynchophylline acts as noncompetitive antagonists of NMDA receptor channels in Xenopus oocytes.
In vitro activity:
Rhy protected NT2 neurons from the damage induced by DA. The expression of Bcl-2 protein was not affected by Rhy.
Reference: Acta Pharmacol Sin. 2002 May;23(5):445-9. https://pubmed.ncbi.nlm.nih.gov/11978195/
In vivo activity:
Rhy inhibits methamphetamine dependence via modulating the miR-181a-5p/GABRA1 axis, which may be a promising target for treatment of methamphetamine dependence.
Reference: J Ethnopharmacol. 2023 Oct 5;314:116635. https://pubmed.ncbi.nlm.nih.gov/37182675/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
2.0 |
5.20 |
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
384.47
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 |
Formulation protocol:
1. Zhou JY, Chen J, Zhou SW, Mo ZX. Individual and combined effects of rhynchophylline and ketamine on proliferation, NMDAR1 and GluA2/3 protein expression in PC12 cells. Fitoterapia. 2013 Mar;85:125-9. doi: 10.1016/j.fitote.2013.01.012. Epub 2013 Jan 23. PMID: 23352746.
2. Shi JS, Kenneth HG. Effect of rhynchophylline on apoptosis induced by dopamine in NT2 cells. Acta Pharmacol Sin. 2002 May;23(5):445-9. PMID: 11978195.
3. Jiang MJ, Li J, Luo CH, Zhu C, Chen ZJ, Bai W, Hu TY, Feng CH, Li C, Mo ZX. Rhynchophylline inhibits methamphetamine dependence via modulating the miR-181a-5p/GABRA1 axis. J Ethnopharmacol. 2023 Oct 5;314:116635. doi: 10.1016/j.jep.2023.116635. Epub 2023 May 13. PMID: 37182675.
4. Lin H, Xie L, Lv L, Chen J, Feng F, Liu W, Han L, Liu F. Intranasally administered thermosensitive gel for brain-targeted delivery of rhynchophylline to treat Parkinson's disease. Colloids Surf B Biointerfaces. 2023 Feb;222:113065. doi: 10.1016/j.colsurfb.2022.113065. Epub 2022 Nov 30. PMID: 36473372.
In vitro protocol:
1. Zhou JY, Chen J, Zhou SW, Mo ZX. Individual and combined effects of rhynchophylline and ketamine on proliferation, NMDAR1 and GluA2/3 protein expression in PC12 cells. Fitoterapia. 2013 Mar;85:125-9. doi: 10.1016/j.fitote.2013.01.012. Epub 2013 Jan 23. PMID: 23352746.
2. Shi JS, Kenneth HG. Effect of rhynchophylline on apoptosis induced by dopamine in NT2 cells. Acta Pharmacol Sin. 2002 May;23(5):445-9. PMID: 11978195.
In vivo protocol:
1. Jiang MJ, Li J, Luo CH, Zhu C, Chen ZJ, Bai W, Hu TY, Feng CH, Li C, Mo ZX. Rhynchophylline inhibits methamphetamine dependence via modulating the miR-181a-5p/GABRA1 axis. J Ethnopharmacol. 2023 Oct 5;314:116635. doi: 10.1016/j.jep.2023.116635. Epub 2023 May 13. PMID: 37182675.
2. Lin H, Xie L, Lv L, Chen J, Feng F, Liu W, Han L, Liu F. Intranasally administered thermosensitive gel for brain-targeted delivery of rhynchophylline to treat Parkinson's disease. Colloids Surf B Biointerfaces. 2023 Feb;222:113065. doi: 10.1016/j.colsurfb.2022.113065. Epub 2022 Nov 30. PMID: 36473372.
1: Ng YP, Or TC, Ip NY. Plant alkaloids as drug leads for Alzheimer's disease. Neurochem Int. 2015 Oct;89:260-70. doi: 10.1016/j.neuint.2015.07.018. Epub 2015 Jul 26. Review. PubMed PMID: 26220901.
2: Zhang Q, Zhao JJ, Xu J, Feng F, Qu W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol. 2015 Sep 15;173:48-80. doi: 10.1016/j.jep.2015.06.011. Epub 2015 Jun 17. Review. PubMed PMID: 26091967.
3: Tognolini M, Incerti M, Lodola A. Are we using the right pharmacological tools to target EphA4? ACS Chem Neurosci. 2014 Dec 17;5(12):1146-7. doi: 10.1021/cn500285h. Epub 2014 Nov 18. Review. PubMed PMID: 25405504.
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5: Zhou JY, Zhou SW. Isorhynchophylline: A plant alkaloid with therapeutic potential for cardiovascular and central nervous system diseases. Fitoterapia. 2012 Jun;83(4):617-26. doi: 10.1016/j.fitote.2012.02.010. Epub 2012 Mar 2. Review. PubMed PMID: 22406453.
6: Zhou J, Zhou S. Antihypertensive and neuroprotective activities of rhynchophylline: the role of rhynchophylline in neurotransmission and ion channel activity. J Ethnopharmacol. 2010 Oct 28;132(1):15-27. doi: 10.1016/j.jep.2010.08.041. Epub 2010 Aug 22. Review. PubMed PMID: 20736055.
7: Shi JS, Yu JX, Chen XP, Xu RX. Pharmacological actions of Uncaria alkaloids, rhynchophylline and isorhynchophylline. Acta Pharmacol Sin. 2003 Feb;24(2):97-101. Review. PubMed PMID: 12546715.
8: Sutter MC, Wang YX. Recent cardiovascular drugs from Chinese medicinal plants. Cardiovasc Res. 1993 Nov;27(11):1891-901. Review. PubMed PMID: 8287391.
