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MedKoo Cat#: 597901 | Name: Roemerine
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Description:

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

Roemerine is an aporphine alkaloid isolated from root tubers of Stephania kwangsiensis H.S. Lo. with potential antifungal properties.

Chemical Structure

Roemerine
Roemerine
CAS#548-08-3

Theoretical Analysis

MedKoo Cat#: 597901

Name: Roemerine

CAS#: 548-08-3

Chemical Formula: C18H17NO2

Exact Mass: 279.1259

Molecular Weight: 279.33

Elemental Analysis: C, 77.40; H, 6.13; N, 5.01; O, 11.45

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 750.00 2 Weeks
10mg USD 1,200.00 2 Weeks
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Related CAS #
No Data
Synonym
Roemerine; Roemerin; CCRIS 3809;
IUPAC/Chemical Name
(R)-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline
InChi Key
JCTYWRARKVGOBK-CQSZACIVSA-N
InChi Code
InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3/t14-/m1/s1
SMILES Code
CN1CCC(C2=C3C4=CC=CC=C4C[C@@]12[H])=CC5=C3OCO5
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 279.33 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
1: Bayazeid O, Nemutlu E, Eylem CC, İlhan M, Küpeli-Akkol E, Karahan H, Kelicen- Uğur P, Ersoz T, Yalçın FN. Neuroactivity of the naturally occurring aporphine alkaloid, roemerine. Nat Prod Res. 2021 Dec;35(24):6147-6152. doi: 10.1080/14786419.2020.1830395. Epub 2020 Oct 7. PMID: 33025828. 2: Ma C, Du F, Yan L, He G, He J, Wang C, Rao G, Jiang Y, Xu G. Potent Activities of Roemerine against Candida albicans and the Underlying Mechanisms. Molecules. 2015 Sep 29;20(10):17913-28. doi: 10.3390/molecules201017913. PMID: 26426004; PMCID: PMC6332056. 3: Yin S, Rao G, Wang J, Luo L, He G, Wang C, Ma C, Luo X, Hou Z, Xu G. Roemerine Improves the Survival Rate of Septicemic BALB/c Mice by Increasing the Cell Membrane Permeability of Staphylococcus aureus. PLoS One. 2015 Nov 25;10(11):e0143863. doi: 10.1371/journal.pone.0143863. PMID: 26606133; PMCID: PMC4659618. 4: Ma HB, Tian ZS, Gui SL, Cui WG, Li W. [Anti-prostate cancer effect of roemerine: An experimental study]. Zhonghua Nan Ke Xue. 2017 Jan;23(1):27-33. Chinese. PMID: 29658233. 5: You M, Wickramaratne DB, Silva GL, Chai H, Chagwedera TE, Farnsworth NR, Cordell GA, Kinghorn AD, Pezzuto JM. (-)-Roemerine, an aporphine alkaloid from Annona senegalensis that reverses the multidrug-resistance phenotype with cultured cells. J Nat Prod. 1995 Apr;58(4):598-604. doi: 10.1021/np50118a021. PMID: 7623038. 6: Avci FG, Atas B, Aksoy CS, Kurpejovic E, Gulsoy Toplan G, Gurer C, Guillerminet M, Orelle C, Jault JM, Sariyar Akbulut B. Repurposing bioactive aporphine alkaloids as efflux pump inhibitors. Fitoterapia. 2019 Nov;139:104371. doi: 10.1016/j.fitote.2019.104371. Epub 2019 Oct 16. PMID: 31629051. 7: Heng HL, Chee CF, Chin SP, Ouyang Y, Wang H, Buckle MJC, Herr DR, Paterson IC, Doughty SW, Abd Rahman N, Chung LY. Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists. Medchemcomm. 2018 Feb 26;9(3):576-582. doi: 10.1039/c7md00629b. Erratum in: Medchemcomm. 2018 Mar 7;9(3):593-594. doi: 10.1039/c8md90012d. PMID: 30108948; PMCID: PMC6072365. 8: Ayyildiz D, Arga KY, Avci FG, Altinisik FE, Gurer C, Gulsoy Toplan G, Kazan D, Wozny K, Brügger B, Mertoglu B, Sariyar Akbulut B. Transcriptomic analysis displays the effect of (-)-roemerine on the motility and nutrient uptake in Escherichia coli. Curr Genet. 2017 Aug;63(4):709-722. doi: 10.1007/s00294-016-0673-4. Epub 2016 Dec 24. PMID: 28013396. 9: Bayazeid O, Eylem CC, Reçber T, Yalçın FN, Kır S, Nemutlu E. An LC-ESI-MS/MS method for the simultaneous determination of pronuciferine and roemerine in some Papaver species. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Oct 1;1096:223-227. doi: 10.1016/j.jchromb.2018.08.020. Epub 2018 Aug 21. PMID: 30189375. 10: Gokgoz NB, Akbulut BS. Proteomics Evidence for the Activity of the Putative Antibacterial Plant Alkaloid (-)-Roemerine: Mainstreaming Omics-Guided Drug Discovery. OMICS. 2015 Aug;19(8):478-89. doi: 10.1089/omi.2015.0056. PMID: 26230533. 11: Liu YQ, He GH, Li HL, He JC, Feng EF, Bai L, Wang CY, Xu GL. Plasma pharmacokinetics and tissue distribution study of roemerine in rats by liquid chromatography with tandem mass spectrometry (LC-MS/MS). J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Oct 15;969:249-55. doi: 10.1016/j.jchromb.2014.08.031. Epub 2014 Aug 28. PMID: 25195027. 12: Wang FX, Zhu N, Zhou F, Lin DX. Natural Aporphine Alkaloids with Potential to Impact Metabolic Syndrome. Molecules. 2021 Oct 10;26(20):6117. doi: 10.3390/molecules26206117. PMID: 34684698; PMCID: PMC8540223. 13: Avci FG, Sayar NA, Sariyar Akbulut B. An OMIC approach to elaborate the antibacterial mechanisms of different alkaloids. Phytochemistry. 2018 May;149:123-131. doi: 10.1016/j.phytochem.2017.12.023. Epub 2018 Feb 27. PMID: 29494814. 14: Jafaar HJ, Isbilen O, Volkan E, Sariyar G. Alkaloid profiling and antimicrobial activities of Papaver glaucum and P. decaisnei. BMC Res Notes. 2021 Sep 8;14(1):348. doi: 10.1186/s13104-021-05762-x. PMID: 34496958; PMCID: PMC8424945. 15: Valiente M, D'Ocon P, Noguera MA, Cassels BK, Lugnier C, Ivorra MD. Vascular activity of (-)-anonaine, (-)-roemerine and (-)-pukateine, three natural 6a(R)-1,2-methylenedioxyaporphines with different affinities for alpha1-adrenoceptor subtypes. Planta Med. 2004 Jul;70(7):603-9. doi: 10.1055/s-2004-827181. PMID: 15254852. 16: Heng HL, Chee CF, Chin SP, Ouyang Y, Wang H, Buckle MJC, Herr DR, Paterson IC, Doughty SW, Abd Rahman N, Chung LY. Correction: Synthesis and evaluation of nuciferine and roemerine enantiomers as 5-HT2 and α1 receptor antagonists. Medchemcomm. 2018 Mar 7;9(3):593-594. doi: 10.1039/c8md90012d. Erratum for: Medchemcomm. 2018 Feb 26;9(3):576-582. doi: 10.1039/c7md00629b. PMID: 30288212; PMCID: PMC6144813. 17: Liu Y, Chen Q, Zhang S, Zhang H, Xu W. Evaluation of green and efficient deep eutectic solvents as media for extracting alkaloids from lotus leaf. Biomed Chromatogr. 2022 Mar;36(3):e5293. doi: 10.1002/bmc.5293. Epub 2021 Dec 30. PMID: 34873711. 18: Barton DH, Bhakuni DS, Chapman GM, Kirby GW. Phenol oxidation and biosynthesis. XV. The biosynthesis of roemerine, anonaine, and mecambrine. J Chem Soc Perkin 1. 1967;21:2134-40. doi: 10.1039/j39670002134. PMID: 6070189. 19: Han Y, Hou T, Zhang ZH, Zhu YH, Cheng JX, Zhou H, Wang JX, Feng JT, Liu YF, Guo ZM, Liang XM. Corybungines A-K: Isoquinoline alkaloids from Corydalis bungeana with dopamine D2 receptor activity. Phytochemistry. 2022 Jul;199:113209. doi: 10.1016/j.phytochem.2022.113209. Epub 2022 Apr 14. PMID: 35430251. 20: Desgrouas C, Taudon N, Bun SS, Baghdikian B, Bory S, Parzy D, Ollivier E. Ethnobotany, phytochemistry and pharmacology of Stephania rotunda Lour. J Ethnopharmacol. 2014 Jul 3;154(3):537-63. doi: 10.1016/j.jep.2014.04.024. Epub 2014 Apr 25. PMID: 24768769.

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