Hypaconitine
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MedKoo CAT#: 540206

CAS#: 6900-87-4

Description: Hypaconitine is a voltage-gated Na channel modulator found in Aconitum. It inhibits end plate potentials in isolated phrenic nerve-diaphragm muscles, blocking transmission at the neuromuscular junction.


Chemical Structure

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Hypaconitine
CAS# 6900-87-4

Theoretical Analysis

MedKoo Cat#: 540206
Name: Hypaconitine
CAS#: 6900-87-4
Chemical Formula: C33H45NO10
Exact Mass: 615.30
Molecular Weight: 615.720
Elemental Analysis: C, 64.37; H, 7.37; N, 2.27; O, 25.98

Price and Availability

Size Price Availability Quantity
10mg USD 350 2 Weeks
25mg USD 700 2 Weeks
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Synonym: Hypaconitine

IUPAC/Chemical Name: (3S,6S,6aS,7R,7aR,8R,9R,10S,11S,11aR,12R,12aR,13R,14R)-11a-acetoxy-9,11-dihydroxy-6,10,13-trimethoxy-3-(methoxymethyl)-1-methyltetradecahydro-2H-3,6a,12-(epiethane[1,1,2]triyl)-7,9-methanonaphtho[2,3-b]azocin-8-yl benzoate

InChi Key: FIDOCHXHMJHKRW-FBYRGYIKSA-N

InChi Code: InChI=1S/C33H45NO10/c1-17(35)44-33-21-19(14-31(38,28(42-6)26(33)36)27(21)43-29(37)18-10-8-7-9-11-18)32-20(40-4)12-13-30(16-39-3)15-34(2)25(32)22(33)23(41-5)24(30)32/h7-11,19-28,36,38H,12-16H2,1-6H3/t19-,20+,21-,22+,23+,24-,25-,26+,27-,28+,30+,31-,32+,33-/m1/s1

SMILES Code: COC[C@@]12CC[C@@H]([C@@]34[C@@H]5C[C@@]6([C@H]([C@@H]([C@@]([C@H]5[C@H]6OC(c7ccccc7)=O)([C@H]([C@H]4N(C2)C)[C@@H]([C@H]13)OC)OC(C)=O)O)OC)O)OC

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: >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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 615.72 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: Xie S, Jia Y, Liu A, Dai R, Huang L. Hypaconitine-induced QT prolongation mediated through inhibition of KCNH2 (hERG) potassium channels in conscious dogs. J Ethnopharmacol. 2015 May 26;166:375-9. doi: 10.1016/j.jep.2015.03.023. Epub 2015 Mar 20. PubMed PMID: 25800797.

2: Shen H, Wu J, Di LQ, Zhu LY, Xu J, Yan R, Li SL. Enhancement by Glycyrrhizae Radix of hepatic metabolism of hypaconitine, a major bioactive and toxic component of Aconiti Laterlis Radix, evaluated by HPLC-TQ-MS/MS analysis. Biomed Chromatogr. 2013 May;27(5):556-62. doi: 10.1002/bmc.2825. Epub 2012 Oct 2. PubMed PMID: 23027546.

3: Yi M, Peng W, Chen X, Wang J, Chen Y. Effect of hypaconitine combined with liquiritin on the expression of calmodulin and connexin43 in rat cardiac muscle in vivo. J Pharm Pharmacol. 2012 Nov;64(11):1654-8. doi: 10.1111/j.2042-7158.2012.01532.x. Epub 2012 May 11. PubMed PMID: 23058053.

4: Zhang PP, Zhang JZ, Wang ZH, Lu YJ, Jiang Y. [Determination of aconitine, hypaconitine and mesaconitine in Shenfu injection]. Zhongguo Zhong Yao Za Zhi. 2013 May;38(10):1521-5. Chinese. PubMed PMID: 23947129.

5: Xin Y, Pi Z, Song F, Liu Z, Liu S. [Comparison of intracorporal absorption of hypaconitine in Heishunpian decoction and its compound recipe decoction by ultra performance liquid chromatography-quadrupole time-of-flight mass spectrometry]. Se Pu. 2011 May;29(5):389-93. Chinese. PubMed PMID: 21847970.

6: Zhang W, Zhang H, Sun S, Sun FF, Chen J, Zhao L, Zhang GQ. Comparative pharmacokinetics of hypaconitine after oral administration of pure hypaconitine, Aconitum carmichaelii extract and Sini Decoction to rats. Molecules. 2015 Jan 16;20(1):1560-70. doi: 10.3390/molecules20011560. PubMed PMID: 25603501.

7: Ye L, Yang X, Yang Z, Gao S, Yin T, Liu W, Wang F, Hu M, Liu Z. The role of efflux transporters on the transport of highly toxic aconitine, mesaconitine, hypaconitine, and their hydrolysates, as determined in cultured Caco-2 and transfected MDCKII cells. Toxicol Lett. 2013 Feb 4;216(2-3):86-99. doi: 10.1016/j.toxlet.2012.11.011. Epub 2012 Nov 28. PubMed PMID: 23200901.

8: Liu X, Li H, Song X, Qin K, Guo H, Wu L, Cai H, Cai B. Comparative pharmacokinetics studies of benzoylhypaconine, benzoylmesaconine, benzoylaconine and hypaconitine in rats by LC-MS method after administration of Radix Aconiti Lateralis Praeparata extract and Dahuang Fuzi Decoction. Biomed Chromatogr. 2014 Jul;28(7):966-73. doi: 10.1002/bmc.3102. Epub 2013 Dec 17. PubMed PMID: 24343604.

9: Yang Y, Huang J, Liu X, Bai M, Ma C, Zhang B. [Difference of hypaconitine concentration in serum between cold-deficiency and normal mice]. Zhongguo Zhong Yao Za Zhi. 2010 Aug;35(15):2008-11. Chinese. PubMed PMID: 20931857.

10: Li C, Jiang Y. [Determination of aconitine and hypaconitine in Gucixiaotong Ye by capillary electrophoresis with field-amplified sample injection]. Zhongguo Zhong Yao Za Zhi. 2010 Dec;35(24):3287-90. Chinese. PubMed PMID: 21438391.

11: Ye L, Gao S, Feng Q, Liu W, Yang Z, Hu M, Liu Z. Development and validation of a highly sensitive UPLC-MS/MS method for simultaneous determination of aconitine, mesaconitine, hypaconitine, and five of their metabolites in rat blood and its application to a pharmacokinetics study of aconitine, mesaconitine, and hypaconitine. Xenobiotica. 2012 Jun;42(6):518-25. doi: 10.3109/00498254.2011.641608. Epub 2011 Dec 22. PubMed PMID: 22188409.

12: Zhang M, Long Y, Sun Y, Wang Y, Li Q, Wu H, Guo Z, Li Y, Niu Y, Li C, Liu L, Mei Q. Evidence for the complementary and synergistic effects of the three-alkaloid combination regimen containing berberine, hypaconitine and skimmianine on the ulcerative colitis rats induced by trinitrobenzene-sulfonic acid. Eur J Pharmacol. 2011 Jan 25;651(1-3):187-96. doi: 10.1016/j.ejphar.2010.10.030. Epub 2010 Oct 20. PubMed PMID: 20969848.

13: Ye L, Wang T, Yang C, Tang L, Zhou J, Lv C, Gong Y, Jiang Z, Liu Z. Microsomal cytochrome P450-mediated metabolism of hypaconitine, an active and highly toxic constituent derived from Aconitum species. Toxicol Lett. 2011 Jul 4;204(1):81-91. doi: 10.1016/j.toxlet.2011.04.015. Epub 2011 Apr 27. PubMed PMID: 21550385.

14: Bai Y, Du S, Li F, Huang F, Deng R, Zhou J, Chen D. Histone deacetylase-high mobility group box-1 pathway targeted by hypaconitine suppresses the apoptosis of endothelial cells. Exp Biol Med (Maywood). 2017 Mar;242(5):527-535. doi: 10.1177/1535370216685433. Epub 2017 Jan 5. PubMed PMID: 28056545; PubMed Central PMCID: PMC5367659.

15: Kimura M, Muroi M, Kimura I, Sakai S, Kitagawa I. Hypaconitine, the dominant constituent responsible for the neuromuscular blocking action of the Japanese-sino medicine "bushi" (aconite root). Jpn J Pharmacol. 1988 Oct;48(2):290-3. PubMed PMID: 3210453.

16: Muroi M, Kimura I, Kimura M. Blocking effects of hypaconitine and aconitine on nerve action potentials in phrenic nerve-diaphragm muscles of mice. Neuropharmacology. 1990 Jun;29(6):567-72. PubMed PMID: 2385329.

17: Zheng LL, Li Y, Zi TY, Yuan MY. 8β-Acet-oxy-14α-benzo-yloxy-N-methyl-13β,15α-dihy-droxy-1α,6α,16β-trimeth-oxy-4β- (meth-oxy-meth-yl)aconitane: hypaconitine isolated from 'fuzi'. Acta Crystallogr Sect E Struct Rep Online. 2010 Oct 9;66(Pt 11):o2787-8. doi: 10.1107/S1600536810039887. PubMed PMID: 21588985; PubMed Central PMCID: PMC3009068.

18: Yu B, Cao Y, Xiong YK. Pharmacokinetics of aconitine-type alkaloids after oral administration of Fuzi (Aconiti Lateralis Radix Praeparata) in rats with chronic heart failure by microdialysis and ultra-high performance liquid chromatography-tandem mass spectrometry. J Ethnopharmacol. 2015 May 13;165:173-9. doi: 10.1016/j.jep.2015.01.057. Epub 2015 Feb 20. PubMed PMID: 25708163.

19: Yang Y, Chen J, Shi YP. Determination of aconitine, hypaconitine and mesaconitine in urine using hollow fiber liquid-phase microextraction combined with high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Oct 15;878(28):2811-6. doi: 10.1016/j.jchromb.2010.08.032. Epub 2010 Sep 16. PubMed PMID: 20846913.

20: Kaneko R, Hattori S, Furuta S, Hamajima M, Hirata Y, Watanabe K, Seno H, Ishii A. Sensitive analysis of aconitine, hypaconitine, mesaconitine and jesaconitine in human body fluids and Aconitum tubers by LC/ESI-TOF-MS. J Mass Spectrom. 2006 Jun;41(6):810-4. PubMed PMID: 16770829.