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MedKoo Cat#: 598672 | Name: Leuconolam

Description:

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

Leuconolam is a 2,7-Seco Aspidosperma alkaloid.

Chemical Structure

Leuconolam
CAS#93710-27-1

Theoretical Analysis

MedKoo Cat#: 598672

Name: Leuconolam

CAS#: 93710-27-1

Chemical Formula: C19H22N2O3

Exact Mass: 326.1630

Molecular Weight: 326.39

Elemental Analysis: C, 69.92; H, 6.79; N, 8.58; O, 14.71

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
Leuconolam; Leuconolam sesquihydrate;
IUPAC/Chemical Name
(8R,12S)-8-ethyl-12-hydroxy-4,5,8,9,10,11-hexahydrobenzo[2,3]azonino[6,5,4-hi]indolizine-6,13(7H,12H)-dione
InChi Key
LCGPZAUIMLPXLP-ZMZPIMSZSA-N
InChi Code
InChI=1S/C19H22N2O3/c1-2-11-5-3-7-13-15-17-12(8-9-14(22)20-16(11)13)6-4-10-21(17)19(24)18(15)23/h4,6,10-11,18,23H,2-3,5,7-9H2,1H3,(H,20,22)/t11-,18+/m1/s1
SMILES Code
O=C(CC1)NC([C@H](CC)CCC2)=C2C3=C4C1=CC=CN4C([C@H]3O)=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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 326.39 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: Xu Z, Wang Q, Zhu J. Enantioselective total syntheses of leuconolam-leuconoxine-mersicarpine group monoterpene indole alkaloids. J Am Chem Soc. 2013 Dec 26;135(51):19127-30. doi: 10.1021/ja4115192. Epub 2013 Dec 13. PubMed PMID: 24328133. 2: Low YY, Hong FJ, Lim KH, Thomas NF, Kam TS. Transformations of the 2,7-Seco Aspidosperma alkaloid leuconolam, structure revision of epi-leuconolam, and partial syntheses of leuconoxine and leuconodines A and F. J Nat Prod. 2014 Feb 28;77(2):327-38. doi: 10.1021/np400922x. Epub 2014 Jan 15. PubMed PMID: 24428198. 3: Li Z, Geng Q, Lv Z, Pritchett BP, Baba K, Numajiri Y, Stoltz BM, Liang G. Selective syntheses of leuconolam, leuconoxine, and mersicarpine alkaloids from a common intermediate through regiocontrolled cyclizations by Staudinger reactions†Electronic supplementary information (ESI) available: Experimental details and procedures, compound characterization data, copies of (1)H and (13)C NMR spectra for new compounds. See DOI: 10.1039/c4qo00312hClick here for additional data file. Org Chem Front. 2015 Mar 17;2(3):236-240. Epub 2015 Jan 27. PubMed PMID: 25717379; PubMed Central PMCID: PMC4333676. 4: Gan CY, Low YY, Thomas NF, Kam TS. Rhazinilam-Leuconolam-Leuconoxine Alkaloids from Leuconotis griffithii. J Nat Prod. 2013 May 24;76(5):957-64. doi: 10.1021/np400214y. Epub 2013 May 6. PubMed PMID: 23647487. 5: Izgu EC, Hoye TR. Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group. Chem Sci. 2013 Feb;4(5):2262-2266. PubMed PMID: 25419448; PubMed Central PMCID: PMC4238231. 6: Xu Z, Wang Q, Zhu J. Total Syntheses of (-)-Mersicarpine, (-)-Scholarisine G, (+)-Melodinine E, (-)-Leuconoxine, (-)-Leuconolam, (-)-Leuconodine A, (+)-Leuconodine F, and (-)-Leuconodine C: Self-Induced Diastereomeric Anisochronism (SIDA) Phenomenon for Scholarisine G and Leuconodines A and C. J Am Chem Soc. 2015 May 27;137(20):6712-24. doi: 10.1021/jacs.5b03619. Epub 2015 May 14. PubMed PMID: 25946614. 7: Yang Y, Bai Y, Sun S, Dai M. Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam. Org Lett. 2014 Dec 5;16(23):6216-9. doi: 10.1021/ol503150c. Epub 2014 Nov 20. PubMed PMID: 25412144; PubMed Central PMCID: PMC4260631. 8: Pfaffenbach M, Gaich T. The Diaza[5.5.6.6]fenestrane Skeleton-Synthesis of Leuconoxine Alkaloids. Chemistry. 2016 Mar 7;22(11):3600-10. doi: 10.1002/chem.201502228. Epub 2015 Oct 7. Review. PubMed PMID: 26443970. 9: Hiller W, Wurst K, Atta-ur-Rahman, Khanum S, Hütter P. Structure of leuconolam sesquihydrate. Acta Crystallogr C. 1989 Aug 15;45 ( Pt 8):1258-60. PubMed PMID: 2604949. 10: Fox Ramos AE, Alcover C, Evanno L, Maciuk A, Litaudon M, Duplais C, Bernadat G, Gallard JF, Jullian JC, Mouray E, Grellier P, Loiseau PM, Pomel S, Poupon E, Champy P, Beniddir MA. Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve. J Nat Prod. 2017 Apr 28;80(4):1007-1014. doi: 10.1021/acs.jnatprod.6b01013. Epub 2017 Mar 10. PubMed PMID: 28282127. 11: Pfaffenbach M, Gaich T. The Rhazinilam-Leuconoxine-Mersicarpine Triad of Monoterpenoid Indole Alkaloids. Alkaloids Chem Biol. 2017;77:1-84. doi: 10.1016/bs.alkal.2016.07.001. Epub 2016 Oct 21. Review. PubMed PMID: 28212700.

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