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MedKoo Cat#: 558586 | Name: Koumine

Description:

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

Koumine is an indole alkaloid. It reverses thermal hyperalgesia and mechanical allodynia induced by sciatic nerve chronic constriction injury (CCI) in rats in a dose-dependent manner. This effect is mediated by elevated allopregnanolone levels in the spinal cord.

Chemical Structure

Koumine
Koumine
CAS#1358-76-5

Theoretical Analysis

MedKoo Cat#: 558586

Name: Koumine

CAS#: 1358-76-5

Chemical Formula: C20H22N2O

Exact Mass: 306.1700

Molecular Weight: 306.40

Elemental Analysis: C, 78.40; H, 7.24; N, 9.14; O, 5.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Koumine;
IUPAC/Chemical Name
(4aR,6R,11cS)-2-methyl-11c-vinyl-1,2,3,4,4a,5,6,11c-octahydro-6,4-(epoxymethano)-3,11b-methanopyrido[4,3-c]carbazole
InChi Key
VTLYEMHGPMGUOT-PVLJVBAISA-N
InChi Code
InChI=1S/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12?,14-,16?,17-,19+,20?/m1/s1
SMILES Code
CN1C[C@@]2(C=C)[C@@H]3C[C@@H]4C5=Nc6c(C52CC1C3CO4)cccc6
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

Preparing Stock Solutions

The following data is based on the product molecular weight 306.40 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
1: Qiu HQ, Xu Y, Jin GL, Yang J, Liu M, Li SP, Yu CX. Koumine enhances spinal cord 3α-hydroxysteroid oxidoreductase expression and activity in a rat model of neuropathic pain. Mol Pain. 2015 Aug 9;11:46. doi: 10.1186/s12990-015-0050-1. PubMed PMID: 26255228; PubMed Central PMCID: PMC4529695. 2: Yang J, Cai HD, Zeng YL, Chen ZH, Fang MH, Su YP, Huang HH, Xu Y, Yu CX. Effects of Koumine on Adjuvant- and Collagen-Induced Arthritis in Rats. J Nat Prod. 2016 Oct 28;79(10):2635-2643. Epub 2016 Sep 22. PubMed PMID: 27657857. 3: Ling Q, Liu M, Wu MX, Xu Y, Yang J, Huang HH, Yu CX. Anti-allodynic and neuroprotective effects of koumine, a Benth alkaloid, in a rat model of diabetic neuropathy. Biol Pharm Bull. 2014;37(5):858-64. PubMed PMID: 24790009. 4: Xu YK, Yang L, Liao SG, Cao P, Wu B, Hu HB, Guo J, Zhang P. Koumine, Humantenine, and Yohimbane Alkaloids from Gelsemium elegans. J Nat Prod. 2015 Jul 24;78(7):1511-7. doi: 10.1021/np5009619. Epub 2015 Jun 23. PubMed PMID: 26103517. 5: Yuan ZH, Liang ZE, Wu J, Yi JE, Chen XJ, Sun ZL. A Potential Mechanism for the Anti-Apoptotic Property of Koumine Involving Mitochondrial Pathway in LPS-Mediated RAW 264.7 Macrophages. Molecules. 2016 Sep 30;21(10). pii: E1317. PubMed PMID: 27706063. 6: Zhang X, Chen Y, Gao B, Luo D, Wen Y, Ma X. Apoptotic Effect of Koumine on Human Breast Cancer Cells and the Mechanism Involved. Cell Biochem Biophys. 2015 Jun;72(2):411-6. doi: 10.1007/s12013-014-0479-2. PubMed PMID: 25561287. 7: Zhang L, Du L, Lv WW, Zhao QC, Hua W, An Y, Guo T, Wu LJ. Four new koumine metabolites in rat liver microsomes. J Asian Nat Prod Res. 2013;15(1):46-52. doi: 10.1080/10286020.2012.742511. Epub 2013 Jan 17. PubMed PMID: 23323600. 8: Yuan Z, Matias FB, Wu J, Liang Z, Sun Z. Koumine Attenuates Lipopolysaccaride-Stimulated Inflammation in RAW264.7 Macrophages, Coincidentally Associated with Inhibition of NF-κB, ERK and p38 Pathways. Int J Mol Sci. 2016 Mar 22;17(3):430. doi: 10.3390/ijms17030430. PubMed PMID: 27011173; PubMed Central PMCID: PMC4813280. 9: Sun M, Hou X, Gao H, Guo J, Xiao K. Two new koumine-type indole alkaloids from Gelsemium elegans Benth. Molecules. 2013 Jan 31;18(2):1819-25. doi: 10.3390/molecules18021819. PubMed PMID: 23434864. 10: Xu Y, Qiu HQ, Liu H, Liu M, Huang ZY, Yang J, Su YP, Yu CX. Effects of koumine, an alkaloid of Gelsemium elegans Benth., on inflammatory and neuropathic pain models and possible mechanism with allopregnanolone. Pharmacol Biochem Behav. 2012 May;101(3):504-14. doi: 10.1016/j.pbb.2012.02.009. Epub 2012 Feb 16. PubMed PMID: 22366214. 11: Chen JZ, Li Y, Xiao JP, Wu SS, Song HW. Development of a sensitive and rapid UPLC-MS/MS method for the determination of koumine in rat plasma: application to a pharmacokinetic study. Biomed Chromatogr. 2013 Jun;27(6):736-40. doi: 10.1002/bmc.2852. Epub 2012 Dec 7. PubMed PMID: 23225577. 12: Cai J, Lei LS, Chi DB. [Antineoplastic effect of koumine in mice bearing H22 solid tumor]. Nan Fang Yi Ke Da Xue Xue Bao. 2009 Sep;29(9):1851-2. Chinese. PubMed PMID: 19778809. 13: Kitajima M, Watanabe K, Maeda H, Kogure N, Takayama H. Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine. Org Lett. 2016 Apr 15;18(8):1912-5. doi: 10.1021/acs.orglett.6b00661. Epub 2016 Apr 1. PubMed PMID: 27035053. 14: Chi DB, Li L, Sun LS, Ma WF. [Koumine-induced apoptosis of human colonic adenocarcinoma cells: the cell biological mechanism]. Nan Fang Yi Ke Da Xue Xue Bao. 2007 Jul;27(7):994-7. Chinese. PubMed PMID: 17666335. 15: Zhang JY, Wang YX. Gelsemium analgesia and the spinal glycine receptor/allopregnanolone pathway. Fitoterapia. 2015 Jan;100:35-43. doi: 10.1016/j.fitote.2014.11.002. Epub 2014 Nov 11. Review. PubMed PMID: 25447163. 16: Zhang LL, Huang CQ, Zhang ZY, Wang ZR, Lin JM. [Therapeutic effects of koumine on psoriasis: an experimental study in mice]. Di Yi Jun Yi Da Xue Xue Bao. 2005 May;25(5):547-9. Chinese. PubMed PMID: 15897131. 17: Wang Y, Wu S, Chen Z, Zhang H, Zhao W. Inhibitory effects of cytochrome P450 enzymes CYP1A2, CYP2A6, CYP2E1 and CYP3A4 by extracts and alkaloids of Gelsemium elegans roots. J Ethnopharmacol. 2015 May 26;166:66-73. doi: 10.1016/j.jep.2015.03.002. Epub 2015 Mar 10. PubMed PMID: 25764964. 18: Chi DB, Lei LS, Yang HX, Sun LS. [General pharmacology of koumine parenteral solution]. Di Yi Jun Yi Da Xue Xue Bao. 2004 Jan;24(1):32-4. Chinese. PubMed PMID: 14724090. 19: Chi DB, Lei LS, Jin H, Pang JX, Jiang YP. [Study of koumine-induced apoptosis of human colon adenocarcinoma LoVo cells in vitro]. Di Yi Jun Yi Da Xue Xue Bao. 2003 Sep;23(9):911-3. Chinese. PubMed PMID: 13129717. 20: Wang ZR, Huang CQ, Zhang ZY, Zhang LL, Lin JM. [Effect of koumine on proliferation of murine CD4+ T cells purified by magnetic-activated cell sorting in vitro]. Di Yi Jun Yi Da Xue Xue Bao. 2005 May;25(5):562-4. Chinese. PubMed PMID: 15897137.