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MedKoo Cat#: 145386 | Name: Lennoxamine

Description:

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

Lennoxamine is an alkaloid. Lennoxamine is synthesized by transannular cyclization of a 10-membered lactam obtained by intramolecular addition of an aryl radical to a (trimethylsilyl)acetylene.

Chemical Structure

Lennoxamine
Lennoxamine
CAS#95530-38-4

Theoretical Analysis

MedKoo Cat#: 145386

Name: Lennoxamine

CAS#: 95530-38-4

Chemical Formula: C20H19NO5

Exact Mass: 353.1263

Molecular Weight: 353.37

Elemental Analysis: C, 67.98; H, 5.42; N, 3.96; O, 22.64

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
Lennoxamine;
IUPAC/Chemical Name
9,10-dimethoxy-5,6,12b,13-tetrahydro-8H-[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1-a]isoindol-8-one
InChi Key
GIVXYHGHGFITPJ-UHFFFAOYSA-N
InChi Code
1S/C20H19NO5/c1-23-15-4-3-13-14-7-12-9-17-16(25-10-26-17)8-11(12)5-6-21(14)20(22)18(13)19(15)24-2/h3-4,8-9,14H,5-7,10H2,1-2H3
SMILES Code
COC1=C(OC)C2=C(C=C1)C3CC4=C(CCN3C2=O)C=C5OCOC5=C4
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 353.37 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: Taniguchi T, Iwasaki K, Uchiyama M, Tamura O, Ishibashi H. A short synthesis of lennoxamine using a radical cascade. Org Lett. 2005 Sep 29;7(20):4389-90. doi: 10.1021/ol051563o. PMID: 16178540. 2: Ishibashi H. Controlling the regiochemistry of radical cyclizations. Chem Rec. 2006;6(1):23-31. doi: 10.1002/tcr.20069. PMID: 16470801. 3: Fuchs JR, Funk RL. Total synthesis of (+/-)-lennoxamine and (+/-)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins. Org Lett. 2001 Nov 29;3(24):3923-5. doi: 10.1021/ol016795b. PMID: 11720570. 4: Comins DL, Schilling S, Zhang Y. Asymmetric synthesis of 3-substituted isoindolinones: application to the total synthesis of (+)-lennoxamine. Org Lett. 2005 Jan 6;7(1):95-8. doi: 10.1021/ol047824w. PMID: 15624986. 5: Vázquez-Vera Ó, Sánchez-Badillo JS, Islas-Jácome A, Rentería-Gómez MA, Pharande SG, Cortes-García CJ, Rincón-Guevara MA, Ibarra IA, Gámez-Montaño R, González-Zamora E. An efficient Ugi-3CR/aza Diels-Alder/Pomeranz-Fritsch protocol towards novel aza-analogues of (±)-nuevamine, (±)-lennoxamine and magallanesine: a diversity oriented synthesis approach. Org Biomol Chem. 2017 Mar 15;15(11):2363-2369. doi: 10.1039/c6ob02572b. PMID: 28066847. 6: Kise N, Isemoto S, Sakurai T. Electroreductive intramolecular coupling of phthalimides with aromatic aldehydes: application to the synthesis of lennoxamine. J Org Chem. 2011 Dec 2;76(23):9856-60. doi: 10.1021/jo2018735. Epub 2011 Nov 3. PMID: 22022955. 7: Rodríguez G, Cid MM, Saá C, Castedo L, Domínguez D. A Radical Cyclization Approach to Isoindolobenzazepines. Synthesis of Lennoxamine. J Org Chem. 1996 Apr 19;61(8):2780-2782. doi: 10.1021/jo952113k. PMID: 11667113. 8: Yao T, Guo Z, Liang X, Qi L. Regio- and Stereoselective Electrophilic Cyclization Approach for the Protecting-Group-Free Synthesis of Alkaloids Lennoxamine, Chilenine, Fumaridine, 8-Oxypseudoplamatine, and 2- O-(Methyloxy)fagaronine. J Org Chem. 2018 Nov 2;83(21):13370-13380. doi: 10.1021/acs.joc.8b02154. Epub 2018 Oct 12. PMID: 30265534. 9: Gámez Montaño R, Zhu J. Rapid access to tetracyclic ring system of lennoxamine type natural product by combined use of a novel three-component reaction and Pummerer cyclization. Chem Commun (Camb). 2002 Oct 21;(20):2448-9. doi: 10.1039/b207179g. PMID: 12430484. 10: Fuwa H, Sasaki M. An efficient method for the synthesis of enol ethers and enecarbamates. Total syntheses of isoindolobenzazepine alkaloids, lennoxamine and chilenine. Org Biomol Chem. 2007 Jun 21;5(12):1849-53. doi: 10.1039/b706087d. Epub 2007 May 16. PMID: 17551632. 11: Padwa A, Beall LS, Eidell CK, Worsencroft KJ. An approach toward isoindolobenzazepines using the ammonium ylide/Stevens. J Org Chem. 2001 Apr 6;66(7):2414-21. doi: 10.1021/jo001684w. PMID: 11281782. 12: Zhu W, Zhao L, Wang MX. Synthesis of 2,3-Dihydro-1H-azepine and 1H-Azepin-2(3H)-one Derivatives From Intramolecular Condensation between Stable Tertiary Enamides and Aldehydes. J Org Chem. 2015 Dec 18;80(24):12047-57. doi: 10.1021/acs.joc.5b02021. Epub 2015 Nov 13. PMID: 26550677. 13: Onozaki Y, Kurono N, Senboku H, Tokuda M, Orito K. Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions. J Org Chem. 2009 Aug 7;74(15):5486-95. doi: 10.1021/jo900311g. Erratum in: J Org Chem. 2009 Aug 21;74(16):6414. PMID: 19459596. 14: Zhu W, Tong S, Zhu J, Wang MX. Intramolecular Arylation of Tertiary Enamides through Pd(OAc)2-Catalyzed Dehydrogenative Cross-Coupling Reaction: Construction of Fused N-Heterocyclic Scaffolds and Synthesis of Isoindolobenzazepine Alkaloids. J Org Chem. 2019 Mar 1;84(5):2870-2878. doi: 10.1021/acs.joc.9b00010. Epub 2019 Feb 14. PMID: 30735050.