Lappaconitine

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

MedKoo CAT#: 540263

CAS#: 32854-75-4

Description: Lappaconitine is a cardiac Na+ channel blocker found in species of Aconitum. It displays many biological activities, including increasing pain thresholds and downregulating expression of P2X3 receptors in DRG neurons, decreasing paw and ear edema, and inducing negative inotropic activity.


Chemical Structure

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Lappaconitine
CAS# 32854-75-4

Theoretical Analysis

MedKoo Cat#: 540263
Name: Lappaconitine
CAS#: 32854-75-4
Chemical Formula: C32H44N2O8
Exact Mass: 584.3098
Molecular Weight: 584.71
Elemental Analysis: C, 65.73; H, 7.59; N, 4.79; O, 21.89

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Lappaconitine

IUPAC/Chemical Name: (3S,6S,6aS,7S,7aS,8S,9R,10S,11aS,12S,12aR,14S)-1-ethyl-7a,11a-dihydroxy-6,8,10-trimethoxydodecahydro-2H-3,6a,12-(epiethane[1,1,2]triyl)-7,9-methanonaphtho[2,3-b]azocin-3(4H)-yl 2-acetamidobenzoate

InChi Key: NWBWCXBPKTTZNQ-QOQRDJBUSA-N

InChi Code: InChI=1S/C32H44N2O8/c1-6-34-16-29(42-28(36)18-9-7-8-10-21(18)33-17(2)35)12-11-25(40-4)31-23(29)14-20(26(31)34)30(37)15-22(39-3)19-13-24(31)32(30,38)27(19)41-5/h7-10,19-20,22-27,37-38H,6,11-16H2,1-5H3,(H,33,35)/t19-,20+,22+,23-,24+,25+,26-,27+,29-,30+,31+,32+/m1/s1

SMILES Code: CCN1C[C@@]2(CC[C@H](OC)[C@@]34[C@@H]2C[C@@H]([C@@H]13)[C@@]5(O)C[C@H](OC)[C@H]6C[C@@H]4[C@]5(O)[C@H]6OC)OC(=O)c7ccccc7NC(=O)C

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

Preparing Stock Solutions

The following data is based on the product molecular weight 584.71 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

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1: Gong QA, Li M. [Effect of Lappaconitine on Postoperative Pain and Serum Complement 3 and 4 Levels of Cancer Patients Undergoing Rectum Surgery]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2015 Jun;35(6):668-72. Chinese. PubMed PMID: 26242116.

2: Bryzgalov AO, Romanov VE, Tolstikova TG, Shults EE. Lappaconitine: influence of halogen substituent on the antiarrhythmic activity. Cardiovasc Hematol Agents Med Chem. 2013 Sep;11(3):211-7. PubMed PMID: 23763697.

3: Zhu XC, Ge CT, Wang P, Zhang JL, Yu YY, Fu CY. Analgesic effects of lappaconitine in leukemia bone pain in a mouse model. PeerJ. 2015 May 7;3:e936. doi: 10.7717/peerj.936. eCollection 2015. PubMed PMID: 26019998; PubMed Central PMCID: PMC4435501.

4: Yang S, Zhang H, Beier RC, Sun F, Cao X, Shen J, Wang Z, Zhang S. Comparative metabolism of Lappaconitine in rat and human liver microsomes and in vivo of rat using ultra high-performance liquid chromatography-quadrupole/time-of-flight mass spectrometry. J Pharm Biomed Anal. 2015 Jun 10;110:1-11. doi: 10.1016/j.jpba.2015.02.048. Epub 2015 Mar 6. PubMed PMID: 25796978.

5: Wang Q, Li ZJ, Sun L, Gao LY, Li MH, Hao JJ, Zhang X, Sun YM. Pharmacokinetic study of lappaconitine hydrobromide in mice by LC-MS. Yao Xue Xue Bao. 2011 Apr;46(4):432-7. PubMed PMID: 21748973.

6: Sheng LH, Xu M, Xu LQ, Xiong F. [Cytotoxic effect of lappaconitine on non-small cell lung cancer in vitro and its molecular mechanism]. Zhong Yao Cai. 2014 May;37(5):840-3. Chinese. PubMed PMID: 25335293.

7: Sun W, Saldaña MDA, Zhao Y, Wu L, Dong T, Jin Y, Zhang J. Hydrophobic lappaconitine loaded into iota-carrageenan by one step self-assembly. Carbohydr Polym. 2016 Feb 10;137:231-238. doi: 10.1016/j.carbpol.2015.10.060. Epub 2015 Oct 17. PubMed PMID: 26686125.

8: Xu H, Zhong H, Liu M, Xu C, Gao Y. Lappaconitine-loaded microspheres for parenteral sustained release: effects of formulation variables and in vitro characterization. Pharmazie. 2011 Sep;66(9):654-61. PubMed PMID: 22026119.

9: Sun W, Saldaña MD, Fan L, Zhao Y, Dong T, Jin Y, Zhang J. Sulfated polysaccharide heparin used as carrier to load hydrophobic lappaconitine. Int J Biol Macromol. 2016 Mar;84:275-80. doi: 10.1016/j.ijbiomac.2015.12.032. Epub 2015 Dec 17. PubMed PMID: 26706841.

10: Polyakov NE, Simaeva OA, Taraban MB, Leshina TV, Konovalova TA, Kispert LD, Nikitina IA, Pankrushina NA, Tkachev AV. CIDNP and EPR study of phototransformation of lappaconitine derivatives in solution. J Phys Chem B. 2010 Apr 8;114(13):4646-51. doi: 10.1021/jp909166r. PubMed PMID: 20232876.

11: Kintsurashvili L. [CHROMATOSPECTROPHOTOMETRIC METHOD OF QUANTITATIVE ANALYSIS OF LAPPACONITINE IN THE UNDERGROUND PARTS OF ACONITUM ORIENTALE MILL, GROWING IN GEORGIA]. Georgian Med News. 2016 May;(254):103-6. Russian. PubMed PMID: 27348177.

12: Xie FM, Wang HC, Li JH, Shu HL, Jiang JR, Chang JP, Hsieh YY. Studies on the metabolism of lappaconitine in humans. Identification of the metabolites of lappaconitine in human urine by high performance liquid chromatography. Biomed Chromatogr. 1990 Jan;4(1):43-6. PubMed PMID: 2310842.

13: Zhou M, Li Y, Liu C, Ma Y, Mi J, Wang S. Simultaneous determination of lappaconitine hydrobromide and isopropiram fumarate in rabbit plasma by capillary electrophoresis with electrochemiluminescence detection. Electrophoresis. 2012 Aug;33(16):2577-83. doi: 10.1002/elps.201100630. PubMed PMID: 22899266.

14: Ono M, Satoh T. Pharmacological studies of lappaconitine. Analgesic activities. Arzneimittelforschung. 1988 Jul;38(7):892-5. PubMed PMID: 3207434.

15: Han M, Zhong YW, Li XP, Wu Z, Liang WQ, Gao JQ. [Influence of different penetration enhancers on Lappaconitine transcutaneous permeation]. Zhongguo Zhong Yao Za Zhi. 2008 Jun;33(11):1252-5. Chinese. PubMed PMID: 18831198.

16: Chen MG, Wang QH, Lin W. [Clinical study in epidural injection with lappaconitine compound for post-operative analgesia]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 1996 Sep;16(9):525-8. Chinese. PubMed PMID: 9772598.

17: Sun W, Wang Y, Zhang J, Yu K. X-ray structure analysis of lappaconitine. Nat Prod Res. 2009;23(10):960-2. doi: 10.1080/14786410902975616. PubMed PMID: 19521910.

18: Erlikh AD. [The Study of Evidence Base for the Use of Lappaconitine Hydrobromide in Patients With Atrial Fibrillation]. Kardiologiia. 2016 Mar;56(3):48-53. Russian. PubMed PMID: 28294889.

19: Wright SN. Irreversible block of human heart (hH1) sodium channels by the plant alkaloid lappaconitine. Mol Pharmacol. 2001 Feb;59(2):183-92. PubMed PMID: 11160852.

20: Ono M, Satoh T. Pharmacological studies of lappaconitine: supraspinal-spinal interaction in antinociception. Arch Int Pharmacodyn Ther. 1991 Jan-Feb;309:32-41. PubMed PMID: 1888228.