Lycodine

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MedKoo CAT#: 530271

CAS#: 20316-18-1

Description: Lycodine is a bioactive chemical.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-10-28. Prices are subject to change without notice.

Lycodine 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#: 530271
Name: Lycodine
CAS#: 20316-18-1
Chemical Formula: C16H22N2
Exact Mass: 242.1783
Molecular Weight: 242.366
Elemental Analysis: C, 79.29; H, 9.15; N, 11.56


Synonym: Lycodine

IUPAC/Chemical Name: 1H-5,10b-Propano-1,7-phenanthroline, 2,3,4,4a,5,6-hexahydro-12-methyl-, (4aR-(4aalpha,5alpha,10balpha,12R*))-

InChi Key: JJPMUZRSJKMFRK-JXFSHQFZSA-N

InChi Code: InChI=1S/C16H22N2/c1-11-8-12-9-15-14(5-2-6-17-15)16(10-11)13(12)4-3-7-18-16/h2,5-6,11-13,18H,3-4,7-10H2,1H3/t11-,12-,13-,16+/m1/s1

SMILES Code: C[C@H](C1)C[C@@]23C4=CC=CN=C4C[C@]1([H])[C@@]2([H])CCCN3


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

1: Qu SM, Shan BH, Wang HT, Wang S. Lycodine type alkaloids from Lycopodiastrum casuarinoides with cytotoxic and cholinesterase inhibitory activities. Fitoterapia. 2018 Nov;131:86-90. doi: 10.1016/j.fitote.2018.10.021. Epub 2018 Oct 21. PubMed PMID: 30352296.

2: Liu Y, Xu PS, Ren Q, Chen X, Zhou G, Li D, Li XM, Xu KP, Yu X, Tan GS. Lycodine-type alkaloids from Lycopodiastrum casuarinoides and their cholinesterase inhibitory activities. Fitoterapia. 2018 Oct;130:203-209. doi: 10.1016/j.fitote.2018.09.005. Epub 2018 Sep 11. PubMed PMID: 30213757.

3: Wang LL, Hao LJ, Zhou ZB, Zhu XL, Shi ZH, Miyamoto T, Pan K. Lycodine-type alkaloids and their glycosides from Lycopodiastrum casuarinoides. Phytochemistry. 2018 Oct;154:63-72. doi: 10.1016/j.phytochem.2018.06.016. Epub 2018 Jul 5. PubMed PMID: 30006089.

4: Liu YC, Zhang ZJ, Su J, Peng LY, Pan LT, Wu XD, Zhao QS. Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata. Nat Prod Bioprospect. 2017 Oct;7(5):405-411. doi: 10.1007/s13659-017-0140-z. Epub 2017 Jul 25. PubMed PMID: 28744720; PubMed Central PMCID: PMC5655362.

5: Tang Y, Xiong J, Zou Y, Wang W, Huang C, Zhang HY, Hu JF. Annotinolide F and lycoannotines A-I, further Lycopodium alkaloids from Lycopodium annotinum. Phytochemistry. 2017 Nov;143:1-11. doi: 10.1016/j.phytochem.2017.07.003. Epub 2017 Jul 21. PubMed PMID: 28738241.

6: Liu YC, Su J, Wu XD, Zhang ZJ, Fan M, Zhu QF, He J, Li XN, Peng LY, Cheng X, Zhao QS. Five new Lycopodium alkaloids from the aerial parts of Phlegmariurus henryi. Fitoterapia. 2016 Dec;115:148-154. doi: 10.1016/j.fitote.2016.10.005. Epub 2016 Oct 18. PubMed PMID: 27769820.

7: Zhao L, Tsukano C, Kwon E, Shirakawa H, Kaneko S, Takemoto Y, Hirama M. Competent Route to Unsymmetric Dimer Architectures: Total Syntheses of (-)-Lycodine and (-)-Complanadines A and B, and Evaluation of Their Neurite Outgrowth Activities. Chemistry. 2017 Jan 18;23(4):802-812. doi: 10.1002/chem.201604647. Epub 2016 Nov 25. PubMed PMID: 27758009.

8: Armijos C, Gilardoni G, Amay L, Lozano A, Bracco F, Ramirez J, Bec N, Larroque C, Finzi PV, Vidari G. Phytochemical and ethnomedicinal study of Huperzia species used in the traditional medicine of Saraguros in Southern Ecuador; AChE and MAO inhibitory activity. J Ethnopharmacol. 2016 Dec 4;193:546-554. doi: 10.1016/j.jep.2016.09.049. Epub 2016 Sep 28. PubMed PMID: 27686269.

9: Shan SM, Luo JG, Pan K, Zou HY, Kong LY. Rapid screening and identification of lycodine-type alkaloids in Lycopodiaceae and Huperziaceae plants by ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Biomed Chromatogr. 2016 Nov;30(11):1861-1872. doi: 10.1002/bmc.3723. Epub 2016 Apr 27. PubMed PMID: 27012167.

10: Chia YY, Kanthimathi MS, Khoo KS, Rajarajeswaran J, Cheng HM, Yap WS. Antioxidant and cytotoxic activities of three species of tropical seaweeds. BMC Complement Altern Med. 2015 Sep 29;15:339. doi: 10.1186/s12906-015-0867-1. PubMed PMID: 26415532; PubMed Central PMCID: PMC4587585.

11: Shaikh S, Zainab T, Shakil S, Rizvi SM. A neuroinformatics study to compare inhibition efficiency of three natural ligands (Fawcettimine, Cernuine and Lycodine) against human brain acetylcholinesterase. Network. 2015;26(1):25-34. doi: 10.3109/0954898X.2014.994145. Epub 2015 Jan 22. PubMed PMID: 25611730.

12: Wu J, Wang H, Ma Y, Jiang J, Zhan R, Chen Y. Isolation of a new lycodine alkaloid from Lycopodium japonicum. Nat Prod Res. 2015;29(8):735-8. doi: 10.1080/14786419.2014.984184. Epub 2014 Nov 25. PubMed PMID: 25421949.

13: Cifuente DA, Vallejo MG, Ortega MG, Cabrera JL, Martín VS, Tonn CE, Agnese AM, Ardanaz CE. Mass spectrometry studies of lycodine-type Lycopodium alkaloids: sauroxine and N-demethylsauroxine. Rapid Commun Mass Spectrom. 2014 Dec 30;28(24):2690-4. doi: 10.1002/rcm.7061. PubMed PMID: 25380490.

14: Jiang WW, Liu F, Gao X, He J, Cheng X, Peng LY, Wu XD, Zhao QS. Huperserines A-E, Lycopodium alkaloids from Huperzia serrata. Fitoterapia. 2014 Dec;99:72-7. doi: 10.1016/j.fitote.2014.09.005. Epub 2014 Sep 16. PubMed PMID: 25218968.

15: Azuma M, Yoshikawa T, Kogure N, Kitajima M, Takayama H. Biogenetically inspired total syntheses of Lycopodium alkaloids, (+)-flabellidine and (-)-lycodine. J Am Chem Soc. 2014 Aug 20;136(33):11618-21. doi: 10.1021/ja507016g. Epub 2014 Aug 11. PubMed PMID: 25103992.

16: Zhang DB, Chen JJ, Song QY, Zhang L, Gao K. Lycodine-type alkaloids from Lycopodiastrum casuarinoides and their acetylcholinesterase inhibitory activity. Molecules. 2014 Jul 10;19(7):9999-10010. doi: 10.3390/molecules19079999. PubMed PMID: 25014530.

17: Johnson T, Siegel D. Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3512-5. doi: 10.1016/j.bmcl.2014.05.060. Epub 2014 May 27. PubMed PMID: 24930830.

18: Pan K, Luo JG, Kong LY. A new Lycopodium alkaloid from Phlegmariurus fargesii. Chin J Nat Med. 2014 May;12(5):373-6. doi: 10.1016/S1875-5364(14)60046-7. PubMed PMID: 24856761.

19: Tang Y, Fu Y, Xiong J, Li M, Ma GL, Yang GX, Wei BG, Zhao Y, Zhang HY, Hu JF. Casuarinines A-J, lycodine-type alkaloids from Lycopodiastrum casuarinoides. J Nat Prod. 2013 Aug 23;76(8):1475-84. doi: 10.1021/np4003355. Epub 2013 Aug 13. PubMed PMID: 23941108.

20: Uosis-Martin M, Pantoş GD, Mahon MF, Lewis SE. A model system for the synthesis of complanadine alkaloids by "diverted Kondrat'eva" oxazole-olefin cycloaddition. J Org Chem. 2013 Jun 21;78(12):6253-63. doi: 10.1021/jo401014n. Epub 2013 Jun 10. PubMed PMID: 23713565.