Rescinnamine | CAS#24815-24-5 | Angiotensin-converting Enzyme Inhibitor

MedKoo Cat#: 341229 | Name: Rescinnamine

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Description:

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

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is a vinca alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia.

Chemical Structure

Rescinnamine

CAS#24815-24-5

Theoretical Analysis

MedKoo Cat#: 341229

Name: Rescinnamine

CAS#: 24815-24-5

Chemical Formula: C35H42N2O9

Exact Mass: 634.2890

Molecular Weight: 634.73

Elemental Analysis: C, 66.23; H, 6.67; N, 4.41; O, 22.69

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Anaprel, Apoterin, Apoterin S, Rescinnamine; Cartric, CCRIS 4711; CCRIS-4711; CCRIS4711, Cinnaloid, Cinnasil, Moderil, Rescisan, Resealoid, Reserpinine, Scinnamina

IUPAC/Chemical Name

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

InChi Key

SZLZWPPUNLXJEA-JXMROGBWSA-N

InChi Code

InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+

SMILES Code

COC1C(OC(/C=C/C2=CC(OC)=C(OC)C(OC)=C2)=O)CC3CN4CCC5=C(NC6=C5C=CC(OC)=C6)C4CC3C1C(OC)=O

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

In vitro activity:

This study found that repurposed drugs, one being rescinnamine, had high binding affinity to spike protein complexes with ACE receptors in SARS-CoV-2. “Anti-corona” computational models discussed in this article could assist in antiviral drug discovery against SARS-CoV-2 and other coronaviruses. Reference: Comput Struct Biotechnol J. 2021;19:3133-3148. https://pubmed.ncbi.nlm.nih.gov/34055238/

In vivo activity:

Rescinnamin increased ocular blood flow in all eye tissues except retina. The blood flow of iris, ciliary body-iris root, and choroid was increased by rescinnamine for 344%, 234%, and 199%, respectively. These results indicate that rescinnamin could be used to treat ischemic eye diseases in the future. Reference: J Ocul Pharmacol Ther. 1996 Summer;12(2):95-101. https://pubmed.ncbi.nlm.nih.gov/8773925/

Preparing Stock Solutions

The following data is based on the product molecular weight 634.73 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.

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

Formulation protocol:

1. Rajput A, Thakur A, Mukhopadhyay A, Kamboj S, Rastogi A, Gautam S, Jassal H, Kumar M. Prediction of repurposed drugs for Coronaviruses using artificial intelligence and machine learning. Comput Struct Biotechnol J. 2021;19:3133-3148. doi: 10.1016/j.csbj.2021.05.037. Epub 2021 May 24. PMID: 34055238; PMCID: PMC8141697. 2. Adeniyi JN, Adeniyi AA, Moodley R, Nlooto M, Ngcobo M, Gomo E, Conradie J. Unravelling the drugability of MSI2 RNA recognition motif (RRM) protein and the prediction of their effective antileukemia inhibitors from traditional herb concoctions. J Biomol Struct Dyn. 2022 Apr;40(6):2516-2529. doi: 10.1080/07391102.2020.1840442. Epub 2020 Nov 2. PMID: 33131412. 3. Liu SX, Chiang CH, Yao QS, Chiou GC. Increase of ocular blood flow by some phytogenic compounds. J Ocul Pharmacol Ther. 1996 Summer;12(2):95-101. doi: 10.1089/jop.1996.12.95. PMID: 8773925.

In vitro protocol:

In vivo protocol:

1. Liu SX, Chiang CH, Yao QS, Chiou GC. Increase of ocular blood flow by some phytogenic compounds. J Ocul Pharmacol Ther. 1996 Summer;12(2):95-101. doi: 10.1089/jop.1996.12.95. PMID: 8773925.

1: Wiens B, De Luca V. Molecular and biochemical characterization of a benzenoid/phenylpropanoid meta/para-O-methyltransferase from Rauwolfia serpentina roots. Phytochemistry. 2016 Dec;132:5-15. doi: 10.1016/j.phytochem.2016.10.004. Epub 2016 Oct 19. PubMed PMID: 27771009. 2: Fadaeinasab M, Basiri A, Kia Y, Karimian H, Ali HM, Murugaiyah V. New Indole Alkaloids from the Bark of Rauvolfia Reflexa and their Cholinesterase Inhibitory Activity. Cell Physiol Biochem. 2015;37(5):1997-2011. doi: 10.1159/000438560. Epub 2015 Nov 20. PubMed PMID: 26584298. 3: Iqbal M, Alam A, Wani TA, Khalil NY. Simultaneous determination of reserpine, rescinnamine, and yohimbine in human plasma by ultraperformance liquid chromatography tandem mass spectrometry. J Anal Methods Chem. 2013;2013:940861. doi: 10.1155/2013/940861. Epub 2013 Dec 5. PubMed PMID: 24383039; PubMed Central PMCID: PMC3870115. 4: AbdelHafez EM, Diamanduros A, Negureanu L, Luy Y, Bean JH, Zielke K, Crowe B, Vasilyeva A, Clodfelter JE, Aly OM, Abuo-Rahma GE, Scarpinato KD, Salsbury FR Jr, King SB. Computational and synthetic studies towards improving rescinnamine as an inducer of MSH2-dependent apoptosis in cancer treatment. Mol Cancer Biol. 2013;1(1). pii: 44. PubMed PMID: 25485184; PubMed Central PMCID: PMC4254817. 5: Vasilyeva A, Clodfelter JE, Gorczynski MJ, Gerardi AR, King SB, Salsbury F, Scarpinato KD. Parameters of Reserpine Analogs That Induce MSH2/MSH6-Dependent Cytotoxic Response. J Nucleic Acids. 2010 Sep 13;2010. pii: 162018. doi: 10.4061/2010/162018. PubMed PMID: 20936178; PubMed Central PMCID: PMC2946608. 6: Peak E, Chalmers IW, Hoffmann KF. Development and validation of a quantitative, high-throughput, fluorescent-based bioassay to detect schistosoma viability. PLoS Negl Trop Dis. 2010 Jul 27;4(7):e759. doi: 10.1371/journal.pntd.0000759. PubMed PMID: 20668553; PubMed Central PMCID: PMC2910722. 7: Azhar I, Mazhar F, Manzar QN, Hussain I, Shamim S. Colorimetric determination of indolic drugs. Pak J Pharm Sci. 2005 Apr;18(2):48-51. PubMed PMID: 16431399. 8: Azeem SW, Khan MA, Ahmad I. Characterisation of oxidation products of Rauwolfia alkaloids. Pak J Pharm Sci. 2005 Jan;18(1):33-5. PubMed PMID: 16431380. 9: Moore J, Abdul-Manan N, Fejzo J, Jacobs M, Lepre C, Peng J, Xie X. Leveraging structural approaches: applications of NMR-based screening and X-ray crystallography for inhibitor design. J Synchrotron Radiat. 2004 Jan 1;11(Pt 1):97-100. Epub 2003 Nov 28. PubMed PMID: 14646145. 10: Jones HE, Brenwald NP, Owen KA, Gill MJ. A multidrug efflux phenotype mutant of Streptococcus pyogenes. J Antimicrob Chemother. 2003 Mar;51(3):707-10. PubMed PMID: 12615875. 11: Pinotsis N, Calokerinos AC, Baeyens WR. Chemiluminometric determination of reserpine and related alkaloids. Analyst. 2000 Jul;125(7):1307-11. PubMed PMID: 10984927. 12: Ke J, Yancey M, Zhang S, Lowes S, Henion J. Quantitative liquid chromatographic-tandem mass spectrometric determination of reserpine in FVB/N mouse plasma using a "chelating" agent (disodium EDTA) for releasing protein-bound analytes during 96-well liquid-liquid extraction. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):369-80. PubMed PMID: 10901142. 13: Cieri UR. Determination of reserpine and rescinnamine in Rauwolfia serpentina powders and tablets: collaborative study. J AOAC Int. 1998 Mar-Apr;81(2):373-80. PubMed PMID: 9549071. 14: Anderson MA, Wachs T, Henion JD. Quantitative ionspray liquid chromatographic/tandem mass spectrometric determination of reserpine in equine plasma. J Mass Spectrom. 1997 Feb;32(2):152-8. PubMed PMID: 9102199. 15: Liu SX, Chiou GC. Effects of Chinese herbal products on mammalian retinal functions. J Ocul Pharmacol Ther. 1996 Fall;12(3):377-86. Review. PubMed PMID: 8875344. 16: Liu SX, Chiang CH, Yao QS, Chiou GC. Increase of ocular blood flow by some phytogenic compounds. J Ocul Pharmacol Ther. 1996 Summer;12(2):95-101. PubMed PMID: 8773925. 17: Bhat UG, Winter MA, Pearce HL, Beck WT. A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line. Mol Pharmacol. 1995 Oct;48(4):682-9. PubMed PMID: 7476894. 18: Ahmed M, Borsch CM, Neyfakh AA, Schuldiner S. Mutants of the Bacillus subtilis multidrug transporter Bmr with altered sensitivity to the antihypertensive alkaloid reserpine. J Biol Chem. 1993 May 25;268(15):11086-9. PubMed PMID: 8098708. 19: Wang J, Ozsoz M. Hydrophobic stripping voltammetry of antihypertensive drugs at lipid-modified electrodes. Analyst. 1990 Jun;115(6):831-4. PubMed PMID: 1975482. 20: Qian XD, Beck WT. Binding of an optically pure photoaffinity analogue of verapamil, LU-49888, to P-glycoprotein from multidrug-resistant human leukemic cell lines. Cancer Res. 1990 Feb 15;50(4):1132-7. PubMed PMID: 1967551.