Jervine HCl

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

MedKoo CAT#: 596215

CAS#: 60326-37-6

Description: Jervine (11-Ketocyclopamine) is a naturally occuring steroidal alkaloid, and is derived from the Veratrum plant species. Jervine is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. Over the Hedgehog signaling pathway Jervine effectively inhibit the tumor growth using three human tumor xenograft models including lung cancer, pancreatic cancer and basal cell carcinoma. Jervine has the potential to advance to a treatment for different tumors.

Chemical Structure

Jervine HCl
CAS# 60326-37-6

Theoretical Analysis

MedKoo Cat#: 596215
Name: Jervine HCl
CAS#: 60326-37-6
Chemical Formula: C27H40ClNO3
Exact Mass: 461.2697
Molecular Weight: 462.07
Elemental Analysis: C, 70.18; H, 8.73; Cl, 7.67; N, 3.03; O, 10.39

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 or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Jervine HCl; Jervine hydrochloride;

IUPAC/Chemical Name: (3S,3'R,3a'S,6aS,6bS,6'S,7a'R,9R,11aS,11bR)-3-hydroxy-3',6',10,11b-tetramethyl-2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11a,11b-hexadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-11(1H)-one hydrochloride


InChi Code: InChI=1S/C27H39NO3.ClH/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2;/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3;1H/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-;/m0./s1

SMILES Code: O=C1[C@]2([H])[C@]3(C)C(C[C@@H](O)CC3)=CC[C@@]2([H])[C@]4([H])CC[C@]5(O[C@@]6([H])[C@@]([C@H]5C)([H])NC[C@@H](C)C6)C(C)=C41.[H]Cl

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 462.07 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: Bailly B, Richard CA, Sharma G, Wang L, Johansen L, Cao J, Pendharkar V, Sharma DC, Galloux M, Wang Y, Cui R, Zou G, Guillon P, von Itzstein M, Eléouët JF, Altmeyer R. Targeting human respiratory syncytial virus transcription anti-termination factor M2-1 to inhibit in vivo viral replication. Sci Rep. 2016 May 19;6:25806. doi: 10.1038/srep25806. PubMed PMID: 27194388; PubMed Central PMCID: PMC4872165.

2: Park J, Jeon YD, Kim HL, Kim DS, Han YH, Jung Y, Youn DH, Kang J, Yoon D, Jeong MY, Lee JH, Hong SH, Lee J, Um JY. Veratri Nigri Rhizoma et Radix (Veratrum nigrum L.) and Its Constituent Jervine Prevent Adipogenesis via Activation of the LKB1-AMPKα-ACC Axis In Vivo and In Vitro. Evid Based Complement Alternat Med. 2016;2016:8674397. doi: 10.1155/2016/8674397. Epub 2016 Apr 6. PubMed PMID: 27143989; PubMed Central PMCID: PMC4837256.

3: Li Q, Yang KX, Zhao YL, Qin XJ, Yang XW, Liu L, Liu YP, Luo XD. Potent anti-inflammatory and analgesic steroidal alkaloids from Veratrum taliense. J Ethnopharmacol. 2016 Feb 17;179:274-9. doi: 10.1016/j.jep.2015.12.059. Epub 2015 Dec 29. PubMed PMID: 26743225.

4: Wang L, Yao ZP, Li P, Chen SB, So PK, Shi ZQ, Hu B, Liu LF, Xin GZ. Global detection and semi-quantification of Fritillaria alkaloids in Fritillariae Ussuriensis Bulbus by a non-targeted multiple reaction monitoring approach. J Sep Sci. 2016 Jan;39(2):287-95. doi: 10.1002/jssc.201500880. Epub 2015 Dec 7. PubMed PMID: 26530331.

5: Torii D, Soeno Y, Fujita K, Sato K, Aoba T, Taya Y. Embryonic tongue morphogenesis in an organ culture model of mouse mandibular arches: blocking Sonic hedgehog signaling leads to microglossia. In Vitro Cell Dev Biol Anim. 2016 Jan;52(1):89-99. doi: 10.1007/s11626-015-9951-6. Epub 2015 Sep 3. PubMed PMID: 26334330.

6: Noguchi KK, Cabrera OH, Swiney BS, Salinas-Contreras P, Smith JK, Farber NB. Hedgehog regulates cerebellar progenitor cell and medulloblastoma apoptosis. Neurobiol Dis. 2015 Nov;83:35-43. doi: 10.1016/j.nbd.2015.08.020. Epub 2015 Aug 28. PubMed PMID: 26319366; PubMed Central PMCID: PMC4674325.

7: Kang C, Han JH, Oh J, Kulkarni R, Zhou W, Ferreira D, Jang TS, Myung CS, Na M. Steroidal Alkaloids from Veratrum nigrum Enhance Glucose Uptake in Skeletal Muscle Cells. J Nat Prod. 2015 Apr 24;78(4):803-10. doi: 10.1021/np501049g. Epub 2015 Apr 2. PubMed PMID: 25835537.

8: Carlier J, Guitton J, Romeuf L, Bévalot F, Boyer B, Fanton L, Gaillard Y. Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Jan 15;975:65-76. doi: 10.1016/j.jchromb.2014.10.028. Epub 2014 Nov 1. PubMed PMID: 25438245.

9: Aydin T, Cakir A, Kazaz C, Bayrak N, Bayir Y, Taşkesenligil Y. Insecticidal metabolites from the rhizomes of Veratrum album against adults of Colorado potato beetle, Leptinotarsa decemlineata. Chem Biodivers. 2014 Aug;11(8):1192-204. doi: 10.1002/cbdv.201300407. PubMed PMID: 25146763.

10: Kazuma K, Konno K. [Poisoning by accidental ingestion of poisonous plants]. Chudoku Kenkyu. 2013 Jun;26(2):97-101. Review. Japanese. PubMed PMID: 23855239.

11: Ghezali L, Leger DY, Limami Y, Cook-Moreau J, Beneytout JL, Liagre B. Cyclopamine and jervine induce COX-2 overexpression in human erythroleukemia cells but only cyclopamine has a pro-apoptotic effect. Exp Cell Res. 2013 Apr 15;319(7):1043-53. doi: 10.1016/j.yexcr.2013.01.014. Epub 2013 Jan 25. PubMed PMID: 23357584.

12: Balbuena J, Pachon G, Lopez-Torrents G, Aran JM, Castresana JS, Petriz J. ABCG2 is required to control the sonic hedgehog pathway in side population cells with stem-like properties. Cytometry A. 2011 Sep;79(9):672-83. doi: 10.1002/cyto.a.21103. Epub 2011 Jul 19. PubMed PMID: 21774076.

13: Zhou JL, Xin GZ, Shi ZQ, Ren MT, Qi LW, Li HJ, Li P. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A. 2010 Nov 5;1217(45):7109-22. doi: 10.1016/j.chroma.2010.09.019. Epub 2010 Sep 16. PubMed PMID: 20926090.

14: Bechtel LK, Lawrence DT, Haverstick D, Powers JS, Wyatt SA, Croley T, Holstege CP. Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay. Clin Toxicol (Phila). 2010 Jun;48(5):435-42. doi: 10.3109/15563651003733666. PubMed PMID: 20586573.

15: Tang J, Li HL, Shen YH, Jin HZ, Yan SK, Liu XH, Zeng HW, Liu RH, Tan YX, Zhang WD. Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum. Phytother Res. 2010 Jun;24(6):821-6. doi: 10.1002/ptr.3022. PubMed PMID: 20013819.

16: Heretsch P, Rabe S, Giannis A. Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine. Org Lett. 2009 Dec 3;11(23):5410-2. doi: 10.1021/ol902270f. PubMed PMID: 19883099.

17: Wilson CW, Chen MH, Chuang PT. Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium. PLoS One. 2009;4(4):e5182. doi: 10.1371/journal.pone.0005182. Epub 2009 Apr 13. PubMed PMID: 19365551; PubMed Central PMCID: PMC2664476.

18: Grobosch T, Binscheck T, Martens F, Lampe D. Accidental intoxication with Veratrum album. J Anal Toxicol. 2008 Nov-Dec;32(9):768-73. PubMed PMID: 19021933.

19: Cong Y, Wang JH, Wang R, Zeng YM, Liu CD, Li X. A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar. J Asian Nat Prod Res. 2008 Jul-Aug;10(7-8):619-24. doi: 10.1080/10286020802133266. PubMed PMID: 18636372.

20: Tang J, Li HL, Shen YH, Jin HZ, Yan SK, Liu RH, Zhang WD. Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum. Phytother Res. 2008 Aug;22(8):1093-6. doi: 10.1002/ptr.2463. PubMed PMID: 18570211.