Warifteine

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MedKoo CAT#: 585417

CAS#: 38566-54-0

Description: Warifteine is a bisbenzylisoquinoline alkaloid isolated from the Cissampelos sympodialis Eichl (Menispermaceae). This plant is used in the folk medicine for the treatment of airway respiratory diseases.


Chemical Structure

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Warifteine
CAS# 38566-54-0

Theoretical Analysis

MedKoo Cat#: 585417
Name: Warifteine
CAS#: 38566-54-0
Chemical Formula: C36H38Cl2N2O6
Exact Mass: 664.2107
Molecular Weight: 665.608
Elemental Analysis: C, 64.96; H, 5.75; Cl, 10.65; N, 4.21; O, 14.42

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: Warifteine

IUPAC/Chemical Name: (16R)-10,25-dimethoxy-15-methyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.218,21.18,12.027,31.016,35]heptatriaconta-1(30),3(37),4,6(36),8(35),9,11,18,20,24,26,31,33-tridecaene-9,32-diol;dihydrochloride

InChi Key: CBLPWCGOLLZSLR-QDSLRZTOSA-N

InChi Code: InChI=1S/C36H36N2O6.2ClH/c1-38-15-13-25-18-29(41-2)33(39)36-32(25)28(38)17-22-4-6-23(7-5-22)20-43-35-30(42-3)19-24-12-14-37-27(31(24)34(35)40)16-21-8-10-26(44-36)11-9-21;;/h4-11,18-19,28,39-40H,12-17,20H2,1-3H3;2*1H/t28-;;/m1../s1

SMILES Code: OC1=C(OC)C=C2CCN(C)[C@]3([H])CC4=CC=C(C=C4)COC5=C(OC)C=C6CCN=C(C6=C5O)CC7=CC=C(OC1=C23)C=C7.[H]Cl.[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: >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: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 665.608 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: Costa HF, Bezerra-Santos CR, Barbosa Filho JM, Martins MA, Piuvezam MR. Warifteine, a bisbenzylisoquinoline alkaloid, decreases immediate allergic and thermal hyperalgesic reactions in sensitized animals. Int Immunopharmacol. 2008 Apr;8(4):519-25. doi: 10.1016/j.intimp.2007.11.009. Epub 2007 Dec 26. PubMed PMID: 18328442.

2: Alves MF, Scotti MT, Scotti L, Mendonça FJB, Filho JMB, de Melo SAL, Dos Santos SG, de F F M Diniz M. Secondary Metabolites from Cissampelos, A Possible Source for New Leads with Anti-Inflammatory Activity. Curr Med Chem. 2017;24(16):1629-1644. doi: 10.2174/0929867323666161227123411. Review. PubMed PMID: 28029072.

3: Lima TF, Rocha JD, Guimarães-Costa AB, Barbosa-Filho JM, Decoté-Ricardo D, Saraiva EM, Arruda LB, Piuvezam MR, Peçanha LM. Warifteine, an alkaloid purified from Cissampelos sympodialis, inhibits neutrophil migration in vitro and in vivo. J Immunol Res. 2014;2014:752923. doi: 10.1155/2014/752923. Epub 2014 Jun 5. PubMed PMID: 24995347; PubMed Central PMCID: PMC4065748.

4: Assis ÁC, Araújo IG, Lima RP, Almeida MM, Marinho AF, Barbosa-Filho JM, Cruz JS, Silva DF, Medeiros IA. Warifteine, a bisbenzylisoquinoline alkaloid, induces relaxation by activating potassium channels in vascular myocytes. Clin Exp Pharmacol Physiol. 2013 Jan;40(1):37-44. doi: 10.1111/1440-1681.12029. PubMed PMID: 23140478.

5: Bezerra-Santos CR, Vieira-de-Abreu A, Vieira GC, Filho JR, Barbosa-Filho JM, Pires AL, Martins MA, Souza HS, Bandeira-Melo C, Bozza PT, Piuvezam MR. Effectiveness of Cissampelos sympodialis and its isolated alkaloid warifteine in airway hyperreactivity and lung remodeling in a mouse model of asthma. Int Immunopharmacol. 2012 Jun;13(2):148-55. doi: 10.1016/j.intimp.2012.03.014. Epub 2012 Apr 3. PubMed PMID: 22480776.

6: Rocha JD, Decoté-Ricardo D, Redner P, Lopes UG, Barbosa-Filho JM, Piuvezam MR, Arruda LB, Maria Torres Peçanha L. Inhibitory effect of the alkaloid warifteine purified from Cissampelos sympodialis on B lymphocyte function in vitro and in vivo. Planta Med. 2010 Mar;76(4):325-30. doi: 10.1055/s-0029-1186165. Epub 2009 Sep 28. PubMed PMID: 19787569.

7: Melo PS, de Medeiros Cavalcante HM, Barbosa-Filho JM, de Fátima Formiga Melo Diniz M, de Medeiros IA, Haun M. Warifteine and milonine, alkaloids isolated from Cissampelos sympodialis Eichl: cytotoxicity on rat hepatocyte culture and in V79 cells. Toxicol Lett. 2003 Apr 30;142(1-2):143-51. PubMed PMID: 12765248.

8: Alves MF, Ferreira LAMP, Gadelha FAAF, Ferreira LKDP, Felix MB, Scotti MT, Scotti L, de Oliveira KM, Dos Santos SG, Diniz MFFM. Toxicological evaluation in silico and in vivo of secondary metabolites of Cissampelos sympodialis in Mus musculus mice following inhalation. Nat Prod Res. 2019 Mar;33(6):789-795. doi: 10.1080/14786419.2017.1410805. Epub 2017 Dec 4. PubMed PMID: 29199466.

9: De Freitas MR, Côrtes SF, Thomas G, Barbosa Filho JM. Modification of Ca2+ metabolism in the rabbit aorta as a mechanism of spasmolytic action of warifteine, a bisbenzylisoquinoline alkaloid isolated from the leaves of Cissampelos sympodialis Eichl. (Menispermaceae). J Pharm Pharmacol. 1996 Mar;48(3):332-6. PubMed PMID: 8737065.

10: Marinho AF, Barbosa-Filho JM, Oliveira EJ. A validated method for the simultaneous quantitation of bioactive alkaloid markers in the leaf ethanolic extract of Cissampelos sympodialis Eichl.: a phenological variation study. Phytochem Anal. 2012 Sep-Oct;23(5):426-32. doi: 10.1002/pca.1376. Epub 2011 Nov 18. PubMed PMID: 22095622.

11: Cavalcanti da Silva E, Dias Rayol C, Medeiros PL, Figueiredo RC, Piuvezan MR, Brabosa-Filho JM, Fernandes Marinho A, Silva TG, Militão GC, Pimentel Cassilhas AP, Paes de Andrade P. Antileishmanial activity of warifteine: a bisbenzylisoquinoline alkaloid isolated from Cissampelos sympodialis Eichl. (Menispermaceae). ScientificWorldJournal. 2012;2012:516408. doi: 10.1100/2012/516408. Epub 2012 Sep 2. PubMed PMID: 22973173; PubMed Central PMCID: PMC3438738.

12: Cerqueira-Lima AT, Alcântara-Neves NM, de Carvalho LC, Costa RS, Barbosa-Filho JM, Piuvezam M, Momtchilo R, Barboza R, de Jesus Oliveira E, Marinho A, Figueiredo CA. Effects of Cissampelos sympodialis Eichl. and its alkaloid, warifteine, in an experimental model of respiratory allergy to Blomia tropicalis. Curr Drug Targets. 2010 Nov;11(11):1458-67. PubMed PMID: 20583974.

13: Bezerra-Santos CR, Vieira-de-Abreu A, Barbosa-Filho JM, Bandeira-Melo C, Piuvezam MR, Bozza PT. Anti-allergic properties of Cissampelos sympodialis and its isolated alkaloid warifteine. Int Immunopharmacol. 2006 Jul;6(7):1152-60. Epub 2006 Mar 6. PubMed PMID: 16714219.

14: Gorinsky C, Luscombe DK, Nicholls PJ. Neuromuscular blocking and local anaesthetic activities of warifteine hydrochloride, an alkaloid isolated from Cissampelos ovalifolia D.C. J Pharm Pharmacol. 1972 Dec;24:Suppl:147P-148. PubMed PMID: 4144871.

15: Costa HF, Leite FC, Alves AF, Barbosa-Filho JM, dos Santos CR, Piuvezam MR. Managing murine food allergy with Cissampelos sympodialis Eichl (Menispermaceae) and its alkaloids. Int Immunopharmacol. 2013 Oct;17(2):300-8. doi: 10.1016/j.intimp.2013.05.024. Epub 2013 Jun 25. PubMed PMID: 23810408.

16: Semwal DK, Semwal RB, Vermaak I, Viljoen A. From arrow poison to herbal medicine--the ethnobotanical, phytochemical and pharmacological significance of Cissampelos (Menispermaceae). J Ethnopharmacol. 2014 Sep 11;155(2):1011-28. doi: 10.1016/j.jep.2014.06.054. Epub 2014 Jul 2. Review. PubMed PMID: 24997389.

17: Lorenzo VP, Alves MF, Scotti L, Dos Santos SG, de Fatima Formiga Melo Diniz M, Scotti MT. Computational Chemistry Study of Natural Alkaloids and Homemade Databank to Predict Inhibitory Potential Against Key Enzymes in Neurodegenerative Diseases. Curr Top Med Chem. 2017;17(26):2926-2934. doi: 10.2174/1568026617666170821150538. PubMed PMID: 28828994.

18: van Andel T, de Boer HJ, Barnes J, Vandebroek I. Medicinal plants used for menstrual disorders in Latin America, the Caribbean, sub-Saharan Africa, South and Southeast Asia and their uterine properties: a review. J Ethnopharmacol. 2014 Sep 11;155(2):992-1000. doi: 10.1016/j.jep.2014.06.049. Epub 2014 Jun 26. Review. PubMed PMID: 24975195.