Lycoctonine

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MedKoo CAT#: 461438

CAS#: 26000-17-9

Description: Lycoctonine is a C19-diterpenoid alkaloid.


Price and Availability

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Pricing updated 2020-10-29. Prices are subject to change without notice.

Lycoctonine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461438
Name: Lycoctonine
CAS#: 26000-17-9
Chemical Formula: C25H41NO7
Exact Mass: 467.2883
Molecular Weight: 467.6
Elemental Analysis: C, 64.22; H, 8.84; N, 3.00; O, 23.95


Synonym: Lycoctonine; Delsine; Roylin;

IUPAC/Chemical Name: (3S,6S,7R,7aR,8S,9R,10S,11aR,13S,14R)-1-ethyl-3-(hydroxymethyl)-6,8,10,13-tetramethoxydodecahydro-2H-3,6a,12-(epiethane[1,1,2]triyl)-7,9-methanonaphtho[2,3-b]azocine-11a,12-diol

InChi Key: YOTUXHIWBVZAJQ-WZROKYDKSA-N

InChi Code: InChI=1S/C25H41NO7/c1-6-26-11-22(12-27)8-7-16(31-3)24-14-9-13-15(30-2)10-23(28,17(14)18(13)32-4)25(29,21(24)26)20(33-5)19(22)24/h13-21,27-29H,6-12H2,1-5H3/t13-,14-,15+,16+,17-,18+,19-,20+,21?,22+,23-,24?,25?/m1/s1

SMILES Code: CCN1C[C@@]2(CC[C@@H](C34[C@@H]5C[C@@H]6[C@@H](OC)C[C@@]([C@H]5[C@H]6OC)(C([C@H]([C@H]23)OC)(C14)O)O)OC)CO


Technical Data

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


References

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2: Liang XX, Tang P, Chen QH, Wang FP. Synthesis of taxane ABC tricyclic skeleton from lycoctonine. Nat Prod Commun. 2012 Jun;7(6):697-703. PubMed PMID: 22816287.

3: Turabekova MA, Rasulev BF. A QSAR toxicity study of a series of alkaloids with the lycoctonine skeleton. Molecules. 2004 Dec 31;9(12):1194-207. PubMed PMID: 18007512.

4: Hohmann J, Forgo P, Hajdú Z, Varga E, Máthé I. Norditerpenoid alkaloids from Consolida orientalis and complete 1H and 13C NMR signal assignments of some lycoctonine-type alkaloids. J Nat Prod. 2002 Jul;65(7):1069-72. PubMed PMID: 12141879.

5: Wang S, Zhou XL, Gong XM, Fan XY, Lan MS. Norditerpenoid alkaloids from Delphinium anthriscifolium. J Asian Nat Prod Res. 2016;18(2):141-6. doi: 10.1080/10286020.2015.1056522. Epub 2015 Aug 6. PubMed PMID: 26245883.

6: Borcsa B, Fodor L, Csupor D, Forgo P, Molnár A 5th, Hohmann J. Diterpene alkaloids from the roots of Aconitum moldavicum and assessment of Nav 1.2 sodium channel activity of aconitum alkaloids. Planta Med. 2014 Feb;80(2-3):231-6. doi: 10.1055/s-0033-1360278. Epub 2014 Jan 22. PubMed PMID: 24452459.

7: Hardick DJ, Cooper G, Scott-Ward T, Blagbrough IS, Potter BV, Wonnacott S. Conversion of the sodium channel activator aconitine into a potent alpha 7-selective nicotinic ligand. FEBS Lett. 1995 May 22;365(1):79-82. PubMed PMID: 7774720.

8: Zhang ZT, Jian XX, Ding JY, Deng HY, Chao RB, Chen QH, Chen DL, Wang FP. Further Studies on Structure-Cardiac Activity Relationships of Diterpenoid Alkaloids. Nat Prod Commun. 2015 Dec;10(12):2075-84. PubMed PMID: 26882669.

9: Ma X, Jiang S, Zhu D. [Diterpenoid alkaloids from Aconitum bulleyanum Diels]. Zhongguo Zhong Yao Za Zhi. 1998 Nov;23(11):679-80, 703. Chinese. PubMed PMID: 11599346.

10: Nisar M, Ahmad M, Wadood N, Lodhi MA, Shaheen F, Choudhary MI. New diterpenoid alkaloids from Aconitum heterophyllum Wall: Selective butyrylcholinestrase inhibitors. J Enzyme Inhib Med Chem. 2009 Feb;24(1):47-51. doi: 10.1080/14756360801906202 . PubMed PMID: 18615279.

11: Shaheen F, Zeeshan M, Ahmad M, Anjum S, Ali S, Fun HK, Choudhary MI, Atta-ur-Rahman. Norditerpenoid alkaloids from Delphinium nordhagenii. J Nat Prod. 2006 May;69(5):823-5. Erratum in: J Nat Prod. 2006 Aug;69(8):1256. Fun, Hong-Kun [corrected to Fun, Hoong-Kun]. PubMed PMID: 16724850.

12: Yang XH, Jia ZP, Li MX, Zhang RX, Li C. [Study on chemical constituents of Delphinium grandiflorum]. Zhong Yao Cai. 2008 Apr;31(4):524-7. Chinese. PubMed PMID: 18661824.

13: Tashkhodjaev B, Sultankhodjaev MN. 8β-Acet-oxy-14α-benzo-yloxy-N-ethyl-3α,10β,13β,15α-tetra-hydr-oxy-1α,6α,16β-trime th-oxy-4β-(methoxy-methyl-ene)aconitane: aconifine from Aconitum karakolicum Rapaics. Acta Crystallogr Sect E Struct Rep Online. 2009 Jun 10;65(Pt 7):o1543-4. doi: 10.1107/S1600536809021436. PubMed PMID: 21582830; PubMed Central PMCID: PMC2969206.

14: Kurtoğlu S, Sen B, Melikoğlu G, Becker H, Zapp J, Kiemer AK, Meriçli F, Meriçli AH. Diterpenoid alkaloids of Aconitum vulparia Rchb. Z Naturforsch C. 2012 Mar-Apr;67(3-4):103-7. PubMed PMID: 22624325.

15: Pu H, Xu Q, Wang F, Che CT. Two new norditerpenoid alkaloids from Delphinium potaninii. Planta Med. 1996 Oct;62(5):462-4. PubMed PMID: 17252482.

16: Chen Y, Katz A. Isolation of norditerpenoid alkaloids from flowers of aconitum lycoctonum . J Nat Prod. 1999 May;62(5):798-9. PubMed PMID: 10346976.

17: Wang XQ, Song Q, Guo XQ, Yan J. Deltaline from Delphinium delavayi Franch. Acta Crystallogr Sect E Struct Rep Online. 2011 Jan 22;67(Pt 2):o439. doi: 10.1107/S1600536811001681. PubMed PMID: 21523103; PubMed Central PMCID: PMC3051497.

18: Shen XL, Wang FP. mCPBA oxidation of acetyllycoctonine and its new products. Chem Pharm Bull (Tokyo). 2005 Mar;53(3):267-70. PubMed PMID: 15744095.

19: Song ZJ, Chen WQ, Du XY, Yuan YF, Xu HH. Anthriscifolcine A, a C18-diterpenoid alkaloid. Acta Crystallogr Sect E Struct Rep Online. 2011 Jan 15;67(Pt 2):o395. doi: 10.1107/S1600536811001346. PubMed PMID: 21523068; PubMed Central PMCID: PMC3051775.

20: Lee ST, Stegelmeier BL, Panter KE, Pfister JA, Gardner DR, Schoch TK, James LF. Evaluation of vaccination against methyllycaconitine toxicity in mice. J Anim Sci. 2003 Jan;81(1):232-8. PubMed PMID: 12597394. a