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MedKoo Cat#: 561463 | Name: Mesembrenone

Description:

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

Mesembrenone is a selective inhibitor of the serotonin transporter (SERT). Mesembrine and mesembrenone are the main alkaloids of Sceletium tortuosum, a plant species that was used for sedation and analgesia by the KhoiSan, previously known as Hottentots, a tribe in South Africa.

Chemical Structure

Mesembrenone
CAS#468-54-2

Theoretical Analysis

MedKoo Cat#: 561463

Name: Mesembrenone

CAS#: 468-54-2

Chemical Formula: C17H21NO3

Exact Mass: 287.1521

Molecular Weight: 287.36

Elemental Analysis: C, 71.06; H, 7.37; N, 4.87; O, 16.70

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Mesembrenone; (+)-Mesembrenone;
IUPAC/Chemical Name
(3aR,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,7,7a-tetrahydroindol-6-one
InChi Key
HDNHBCSWFYFPAN-IRXDYDNUSA-N
InChi Code
InChI=1S/C17H21NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-7,10,16H,8-9,11H2,1-3H3/t16-,17-/m0/s1
SMILES Code
O=C1C=C[C@@]2(C3=CC=C(OC)C(OC)=C3)CCN(C)[C@@]2([H])C1
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 287.36 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: Krstenansky JL. Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacology. J Ethnopharmacol. 2017 Jan 4;195:10-19. doi: 10.1016/j.jep.2016.12.004. Epub 2016 Dec 7. Review. PubMed PMID: 27939420. 2: Manda VK, Avula B, Ashfaq MK, Abe N, Khan IA, Khan SI. Quantification of mesembrine and mesembrenone in mouse plasma using UHPLC-QToF-MS: Application to a pharmacokinetic study. Biomed Chromatogr. 2017 Mar;31(3). doi: 10.1002/bmc.3815. Epub 2016 Sep 15. PubMed PMID: 27526669. 3: Gan P, Smith MW, Braffman NR, Snyder SA. Pyrone Diels-Alder Routes to Indolines and Hydroindolines: Syntheses of Gracilamine, Mesembrine, and Δ(7) -Mesembrenone. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3625-30. doi: 10.1002/anie.201510520. Epub 2016 Feb 10. PubMed PMID: 26865400. 4: Patnala S, Kanfer I. Medicinal use of Sceletium: Characterization of Phytochemical Components of Sceletium Plant Species using HPLC with UV and Electrospray Ionization--Tandem Mass Spectroscopy. J Pharm Pharm Sci. 2015;18(4):414-23. PubMed PMID: 26626243. 5: Swart AC, Smith C. Modulation of glucocorticoid, mineralocorticoid and androgen production in H295 cells by Trimesemine™, a mesembrine-rich Sceletium extract. J Ethnopharmacol. 2016 Jan 11;177:35-45. doi: 10.1016/j.jep.2015.11.033. Epub 2015 Nov 19. PubMed PMID: 26608706. 6: Konoura K, Fujii H, Imaide S, Gouda H, Hirayama S, Hirono S, Nagase H. Transformation of naltrexone into mesembrane and investigation of the binding properties of its intermediate derivatives to opioid receptors. Bioorg Med Chem. 2015 Feb 1;23(3):439-48. doi: 10.1016/j.bmc.2014.12.032. Epub 2014 Dec 24. PubMed PMID: 25573119. 7: Murbach TS, Hirka G, Szakonyiné IP, Gericke N, Endres JR. A toxicological safety assessment of a standardized extract of Sceletium tortuosum (Zembrin®) in rats. Food Chem Toxicol. 2014 Dec;74:190-9. doi: 10.1016/j.fct.2014.09.017. Epub 2014 Oct 6. PubMed PMID: 25301237. 8: Meyer GM, Wink CS, Zapp J, Maurer HH. GC-MS, LC-MS(n), LC-high resolution-MS(n), and NMR studies on the metabolism and toxicological detection of mesembrine and mesembrenone, the main alkaloids of the legal high "Kanna" isolated from Sceletium tortuosum. Anal Bioanal Chem. 2015 Jan;407(3):761-78. doi: 10.1007/s00216-014-8109-9. Epub 2014 Sep 21. PubMed PMID: 25240931. 9: Pigni NB, Ríos-Ruiz S, Luque FJ, Viladomat F, Codina C, Bastida J. Wild daffodils of the section Ganymedes from the Iberian Peninsula as a source of mesembrane alkaloids. Phytochemistry. 2013 Nov;95:384-93. doi: 10.1016/j.phytochem.2013.07.010. Epub 2013 Aug 8. PubMed PMID: 23932506. 10: Shikanga EA, Hamman JH, Chen W, Combrinck S, Gericke N, Viljoen AM. In vitro permeation of mesembrine alkaloids from Sceletium tortuosum across porcine buccal, sublingual, and intestinal mucosa. Planta Med. 2012 Feb;78(3):260-8. doi: 10.1055/s-0031-1280367. Epub 2011 Nov 21. PubMed PMID: 22105579. 11: Harvey AL, Young LC, Viljoen AM, Gericke NP. Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloids. J Ethnopharmacol. 2011 Oct 11;137(3):1124-9. doi: 10.1016/j.jep.2011.07.035. Epub 2011 Jul 20. PubMed PMID: 21798331. 12: Patnala S, Kanfer I. HPLC analysis of mesembrine-type alkaloids in Sceletium plant material used as an African traditional medicine. J Pharm Pharm Sci. 2010;13(4):558-70. PubMed PMID: 21486531. 13: Patnala S, Kanfer I. Investigations of the phytochemical content of Sceletium tortuosum following the preparation of "Kougoed" by fermentation of plant material. J Ethnopharmacol. 2009 Jan 12;121(1):86-91. doi: 10.1016/j.jep.2008.10.008. Epub 2008 Oct 17. PubMed PMID: 18996176. 14: Patnala S, Kanfer I. A capillary zone electrophoresis method for the assay and quality control of mesembrine in Sceletium tablets. J Pharm Biomed Anal. 2008 Sep 29;48(2):440-6. doi: 10.1016/j.jpba.2008.01.002. Epub 2008 Jan 9. PubMed PMID: 18280080. 15: Weniger B, Italiano L, Beck JP, Bastida J, Bergoñon S, Codina C, Lobstein A, Anton R. Cytotoxic activity of Amaryllidaceae alkaloids. Planta Med. 1995 Feb;61(1):77-9. PubMed PMID: 7701000.

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