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MedKoo Cat#: 145327 | Name: Magellanine

Description:

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

Magellanine is one of three natural products isolated from the Lycopodium family that share a unique 6-5-5-6-fused tetracyclic diquinane core skeleton.

Chemical Structure

Magellanine
Magellanine
CAS#61273-75-4

Theoretical Analysis

MedKoo Cat#: 145327

Name: Magellanine

CAS#: 61273-75-4

Chemical Formula: C17H25NO2

Exact Mass: 275.1885

Molecular Weight: 275.39

Elemental Analysis: C, 74.14; H, 9.15; N, 5.09; O, 11.62

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Magellanine;
IUPAC/Chemical Name
(4aS,6S,6aR,6bS,10aS,11aS)-6-hydroxy-3,9-dimethyl-4,4a,5,6,6a,6b,7,8,9,10,10a,11-dodecahydro-1H-benzo[3a,4]pentaleno[2,1-c]pyridin-1-one
InChi Key
ADRPSBGLUHNVOU-INSRFAMQSA-N
InChi Code
1S/C17H25NO2/c1-10-5-12-7-14(19)16-13-3-4-18(2)9-11(13)8-17(12,16)15(20)6-10/h6,11-14,16,19H,3-5,7-9H2,1-2H3/t11-,12+,13+,14+,16+,17-/m1/s1
SMILES Code
[H][C@]12C[C@]34C(=O)C=C(C)C[C@@]3([H])C[C@H](O)[C@]4([H])[C@@]1([H])CCN(C)C2
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 275.39 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: Saito T, Awad JM, Zhang W. Synthetic Studies on Tetracyclic Diquinane Lycopodium Alkaloids Magellanine, Magellaninone and Paniculatine. Molecules. 2023 Feb 3;28(3):1501. doi: 10.3390/molecules28031501. PMID: 36771167; PMCID: PMC9920116. 2: Huang BB, Lei K, Zhong LR, Yang X, Yao ZJ. Unified Total Synthesis of Tetracyclic Diquinane Lycopodium Alkaloids (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone. J Org Chem. 2022 Jul 1;87(13):8685-8696. doi: 10.1021/acs.joc.2c00871. Epub 2022 Jun 14. PMID: 35699523. 3: Jiang SZ, Lei T, Wei K, Yang YR. Collective total synthesis of tetracyclic diquinane Lycopodium alkaloids (+)-paniculatine, (-)-magellanine, (+)-magellaninone and analogues thereof. Org Lett. 2014 Nov 7;16(21):5612-5. doi: 10.1021/ol502679v. Epub 2014 Oct 9. PMID: 25299586. 4: McGee P, Bétournay G, Barabé F, Barriault L. A 11-Steps Total Synthesis of Magellanine through a Gold(I)-Catalyzed Dehydro Diels-Alder Reaction. Angew Chem Int Ed Engl. 2017 May 22;56(22):6280-6283. doi: 10.1002/anie.201611606. Epub 2017 Jan 12. PMID: 28079949. 5: Kozaka T, Miyakoshi N, Mukai C. Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions. J Org Chem. 2007 Dec 21;72(26):10147-54. doi: 10.1021/jo702136b. Epub 2007 Nov 29. PMID: 18044932. 6: Lin KW, Ananthan B, Tseng SF, Yan TH. Exceedingly Concise and Elegant Synthesis of (+)-Paniculatine, (-)-Magellanine, and (+)-Magellaninone. Org Lett. 2015 Aug 7;17(15):3938-40. doi: 10.1021/acs.orglett.5b01975. Epub 2015 Jul 24. PMID: 26207328. 7: Lindsay VNG, Murphy RA, Sarpong R. Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids. Chem Commun (Camb). 2017 Sep 14;53(74):10291-10294. doi: 10.1039/c7cc06367a. PMID: 28869258; PMCID: PMC6289252. 8: Yen CF, Liao CC. Concise and efficient total synthesis of Lycopodium alkaloid magellanine. Angew Chem Int Ed Engl. 2002 Nov 4;41(21):4090-3. doi: 10.1002/1521-3773(20021104)41:21<4090::AID-ANIE4090>3.0.CO;2-#. PMID: 12412091. 9: Murphy RA, Sarpong R. Direct methoxypyridine functionalization approach to magellanine-type Lycopodium alkaloids. Org Lett. 2012 Jan 20;14(2):632-5. doi: 10.1021/ol203269f. Epub 2011 Dec 27. PMID: 22201223; PMCID: PMC3262889. 10: Hong BC, Wu MF, Tseng HC, Liao JH. Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol. Org Lett. 2006 May 25;8(11):2217-20. doi: 10.1021/ol060486+. PMID: 16706490.