Conessine | CAS#546-06-5 | anti-malarial

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

MedKoo CAT#: 461413

CAS#: 546-06-5

Description: Conessine is a steroidal alkaloid isolated from Holarrhena floribunda that has anti-malarial activity and interacts with the histamine H3 receptor.

Chemical Structure

Conessine

CAS# 546-06-5

Instruction

Theoretical Analysis

MedKoo Cat#: 461413
Name: Conessine
CAS#: 546-06-5
Chemical Formula: C24H40N2
Exact Mass: 356.32
Molecular Weight: 356.590
Elemental Analysis: C, 80.84; H, 11.31; N, 7.86

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 280
100mg	USD 480
250mg	USD 870
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Conessine; Conessinum; Konessin; Neriine; Roquessine; Wrightine;

IUPAC/Chemical Name: (3R,3aR,5aR,5bR,9R,11aS,11bR,13aR)-N,N,2,3,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-naphtho[2',1':4,5]indeno[1,7a-c]pyrrol-9-amine

InChi Key: GPLGAQQQNWMVMM-CQDKKVBOSA-N

InChi Code: InChI=1S/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19-,20+,21-,22-,23-,24+/m1/s1

SMILES Code: CN(C)[C@@H](C1)CC[C@]([C@@H]2CC3)(C)C1=CC[C@H]2[C@H]4CC[C@@H]5[C@]43CN(C)[C@@H]5C

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 356.59 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:
In vitro protocol:
In vivo protocol:

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1: Kim H, Lee KI, Jang M, Namkoong S, Park R, Ju H, Choi I, Oh WK, Park J. Conessine Interferes with Oxidative Stress-Induced C2C12 Myoblast Cell Death through Inhibition of Autophagic Flux. PLoS One. 2016 Jun 3;11(6):e0157096. doi: 10.1371/journal.pone.0157096. eCollection 2016. PubMed PMID: 27257813; PubMed Central PMCID: PMC4892631.

2: Morais-Silva G, Ferreira-Santos M, Marin MT. Conessine, an H3 receptor antagonist, alters behavioral and neurochemical effects of ethanol in mice. Behav Brain Res. 2016 May 15;305:100-7. doi: 10.1016/j.bbr.2016.02.025. Epub 2016 Feb 26. PubMed PMID: 26924015.

3: Siriyong T, Chusri S, Srimanote P, Tipmanee V, Voravuthikunchai SP. Holarrhena antidysenterica Extract and Its Steroidal Alkaloid, Conessine, as Resistance-Modifying Agents Against Extensively Drug-Resistant Acinetobacter baumannii. Microb Drug Resist. 2016 Jun;22(4):273-82. doi: 10.1089/mdr.2015.0194. Epub 2016 Jan 8. PubMed PMID: 26745443.

4: Dua VK, Verma G, Singh B, Rajan A, Bagai U, Agarwal DD, Gupta NC, Kumar S, Rastogi A. Anti-malarial property of steroidal alkaloid conessine isolated from the bark of Holarrhena antidysenterica. Malar J. 2013 Jun 10;12:194. doi: 10.1186/1475-2875-12-194. PubMed PMID: 23758861; PubMed Central PMCID: PMC3685520.

5: Siddiqui BS, Ali ST, Rizwani GH, Begum S, Tauseef S, Ahmad A. Antimicrobial activity of the methanolic bark extract of Holarrhena pubescens (Buch. Ham), its fractions and the pure compound conessine. Nat Prod Res. 2012;26(11):987-92. doi: 10.1080/14786419.2010.537268. Epub 2011 Aug 11. PubMed PMID: 21834632.

6: Zhao C, Sun M, Bennani YL, Gopalakrishnan SM, Witte DG, Miller TR, Krueger KM, Browman KE, Thiffault C, Wetter J, Marsh KC, Hancock AA, Esbenshade TA, Cowart MD. The alkaloid conessine and analogues as potent histamine H3 receptor antagonists. J Med Chem. 2008 Sep 11;51(17):5423-30. doi: 10.1021/jm8003625. Epub 2008 Aug 7. PubMed PMID: 18683917.

7: Patel RK, Prajapati AM. Development and validation of a visible absorption densitometry method for quantitation of conessine in Holarrhena antidysenterica (Kurchi). J AOAC Int. 2008 Mar-Apr;91(2):339-43. PubMed PMID: 18476345.

8: Kaur AD, Ravichandran V, Jain PK, Agrawal RK. High-performance thin layer chromatography method for estimation of conessine in herbal extract and pharmaceutical dosage formulations. J Pharm Biomed Anal. 2008 Jan 22;46(2):391-4. Epub 2007 Oct 6. PubMed PMID: 18006264.

9: Bogne KP, Penlap BV, Lontsi D, Etoa FX. Antibacterial activities of the extracts and conessine from Holarrhena floribunda G. Don. (Apocynaceae). Afr J Tradit Complement Altern Med. 2007 Feb 16;4(3):352-6. PubMed PMID: 20161899; PubMed Central PMCID: PMC2816488.

10: Jiang B, Xu M. Highly enantioselective construction of fused pyrrolidine systems that contain a quaternary stereocenter: concise formal synthesis of (+)-conessine. Angew Chem Int Ed Engl. 2004 May 3;43(19):2543-6. PubMed PMID: 15127448.

11: Santora VJ, Covel JA, Hayashi R, Hofilena BJ, Ibarra JB, Pulley MD, Weinhouse MI, Sengupta D, Duffield JJ, Semple G, Webb RR, Sage C, Ren A, Pereira G, Knudsen J, Edwards JE, Suarez M, Frazer J, Thomsen W, Hauser E, Whelan K, Grottick AJ. A new family of H3 receptor antagonists based on the natural product Conessine. Bioorg Med Chem Lett. 2008 Feb 15;18(4):1490-4. doi: 10.1016/j.bmcl.2007.12.059. Epub 2007 Dec 25. PubMed PMID: 18194865.

12: PIETTE M. [Experimental studies of conessine. Cultures of dysenteric amoeba in mediums to which chlorhydrates of conessine or emetine were previously added]. Ann Pharm Fr. 1950 May;8(5):410-4. Undetermined Language. PubMed PMID: 15433047.

13: MUHLPFORDT H, MARTINEZ-SILVA R. [Effects of isoconessine and neoconessine on Endamoeba histolytica in vitro, as compared with conessine and emetine]. Z Tropenmed Parasitol. 1956 Jun;7(2):211-9. German. PubMed PMID: 13353434.

14: PIETTE M. [Experimental studies on conessine. II. Elimination of conessine in man during treatment of amebic dysentery]. Ann Pharm Fr. 1950 Apr;8(4):316-21. Undetermined Language. PubMed PMID: 15426056.

15: STEPHENSON RP, DUTTA NK. A comparison of the irritant action of conessine, isoconessine, and neoconessine. Br J Pharmacol Chemother. 1948 Dec;3(4):326. PubMed PMID: 18102603; PubMed Central PMCID: PMC1509851.

16: STEPHENSON RP. The pharmacological properties of conessine, isoconessine and neoconessine. Br J Pharmacol Chemother. 1948 Sep;3(3):237-45. PubMed PMID: 18884006; PubMed Central PMCID: PMC1509831.

17: [Conessine (hydrobromide) conessini hydrobromidum: bibromhydrate of conessine]. Ann Pharm Fr. 1953 Dec;11(12):772-4. French. PubMed PMID: 13159012.

18: PIETTE M. [Experimental studies of conessine. Comparative study of the culture medium of dysenteric amoeba after addition of chlorhydrates of conessine or emetine]. Ann Pharm Fr. 1950 May;8(5):402-9. Undetermined Language. PubMed PMID: 15433046.

19: SOULAGE J, PORTE L. [Two cases of amebic hepatitis treated by conessine chlorhydrate]. Med Trop (Mars). 1950 Mar-Apr;10(2):287-90. Undetermined Language. PubMed PMID: 15438296.

20: PIETTE M. [Experimental studies on conessine. V. Action of hydrochlorides of conessine or emetine on cultures of Entamoeba dysenteriae]. Ann Pharm Fr. 1950 Jun;8(6):456-9. Undetermined Language. PubMed PMID: 14771681.

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