Lycoramine free base

MedKoo Cat#: 330152 | Name: Lycoramine free base

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Description:

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

Lycoramine is a natural alkaloid isolated from Lycoris chinensis.

Chemical Structure

Lycoramine free base

CAS#21133-52-8 (free base)

Theoretical Analysis

MedKoo Cat#: 330152

Name: Lycoramine free base

CAS#: 21133-52-8 (free base)

Chemical Formula: C17H23NO3

Exact Mass: 289.1678

Molecular Weight: 289.38

Elemental Analysis: C, 70.56; H, 8.01; N, 4.84; O, 16.59

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 weeks
10mg	USD 850.00	2 weeks

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Related CAS #

21133-52-8 (free base) 89505-76-0 (HBr)

Synonym

Lycoramine free base;

IUPAC/Chemical Name

(4aS,6S,8aR)-3-methoxy-11-methyl-4a,5,7,8,9,10,11,12-octahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol

InChi Key

GJRMHIXYLGOZSE-JDFRZJQESA-N

InChi Code

InChI=1S/C17H23NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-4,12,14,19H,5-10H2,1-2H3/t12-,14-,17-/m0/s1

SMILES Code

O[C@H]1CC[C@@]23C(C(CN(C)CC3)=CC=C4OC)=C4O[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

>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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lycoramine is a potent acetylcholinesterase (AChE) inhibitor.

In vitro activity:

TBD

In vivo activity:

Lycoramine and galantamine, an FDA approved drug used in the treatment of mild to moderate AD, were administered to 12 month-old 5xFAD mice. Bioinformatics analyses showed altered molecular pathways that can be linked with the reversal of cognitive decline observed after lycoramine administration but not with galantamine. Lycoramine shows therapeutic potential to halt and reverse cognitive decline at the late stages of disease progression, and holds great promise for the treatment of Alzheimer's disease. Reference: Curr Med Chem. 2021;28(17):3449-3473. https://pubmed.ncbi.nlm.nih.gov/33200692/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	345.57

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 289.38 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:

1. Kiris I, Basar MK, Sahin B, Gurel B, Coskun J, Mroczek T, Baykal AT. Evaluation of the Therapeutic Effect of Lycoramine on Alzheimer's Disease in Mouse Model. Curr Med Chem. 2021;28(17):3449-3473. doi: 10.2174/0929867327999201116193126. PMID: 33200692.

In vitro protocol:

TBD

In vivo protocol:

1: Rocha REO, Lima LHF. Cooperative hydrogen bonds and mobility of the non-aromatic ring as selectivity determinants for human acetylcholinesterase to similar anti-Alzheimer's galantaminics: a computational study. J Biomol Struct Dyn. 2018 May 17:1-14. doi: 10.1080/07391102.2018.1470036. [Epub ahead of print] PubMed PMID: 29697300. 2: Li L, Yang Q, Wang Y, Jia Y. Catalytic asymmetric total synthesis of (-)-galanthamine and (-)-lycoramine. Angew Chem Int Ed Engl. 2015 May 18;54(21):6255-9. doi: 10.1002/anie.201411338. Epub 2015 Apr 2. PubMed PMID: 25847447. 3: Feng Y, Yu ZX. Formal synthesis of (±)-galanthamine and (±)-lycoramine using Rh(I)-catalyzed [(3 + 2) + 1] cycloaddition of 1-ene-vinylcyclopropane and CO. J Org Chem. 2015 Feb 6;80(3):1952-6. doi: 10.1021/jo502604p. Epub 2015 Jan 16. PubMed PMID: 25558884. 4: Cortes N, Alvarez R, Osorio EH, Alzate F, Berkov S, Osorio E. Alkaloid metabolite profiles by GC/MS and acetylcholinesterase inhibitory activities with binding-mode predictions of five Amaryllidaceae plants. J Pharm Biomed Anal. 2015 Jan;102:222-8. doi: 10.1016/j.jpba.2014.09.022. Epub 2014 Sep 28. PubMed PMID: 25305596. 5: Zhang Y, Li Y, Zhou J, Chen N, Wang M, Dong Z, Gao C, Zhong Y. [Effect of precursor on growth and accumulation of alkaloids of Lycoris radiata suspension cells]. Sheng Wu Gong Cheng Xue Bao. 2014 Feb;30(2):247-54. Chinese. PubMed PMID: 24945053. 6: Jin A, Li X, Zhu YY, Yu HY, Pi HF, Zhang P, Ruan HL. Four new compounds from the bulbs of Lycoris aurea with neuroprotective effects against CoCl₂ and H₂O₂-induced SH-SY5Y cell injuries. Arch Pharm Res. 2014 Mar;37(3):315-23. doi: 10.1007/s12272-013-0188-1. Epub 2013 Jun 18. PubMed PMID: 23775477. 7: Katoch D, Kumar D, Sharma U, Kumar N, Padwad YS, Lal B, Singh B. Zephgrabetaine: a new betaine-type amaryllidaceae alkaloid from Zephyranthes grandiflora. Nat Prod Commun. 2013 Feb;8(2):161-4. PubMed PMID: 23513717. 8: Zhang Y, Chen Z. Nonaqueous CE ESI-IT-MS analysis of Amaryllidaceae alkaloids. J Sep Sci. 2013 Mar;36(6):1078-84. doi: 10.1002/jssc.201201083. Epub 2013 Feb 25. PubMed PMID: 23436771. 9: Katoch D, Kumar S, Kumar N, Singh B. Simultaneous quantification of Amaryllidaceae alkaloids from Zephyranthes grandiflora by UPLC-DAD/ESI-MS/MS. J Pharm Biomed Anal. 2012 Dec;71:187-92. doi: 10.1016/j.jpba.2012.08.001. Epub 2012 Aug 16. PubMed PMID: 22939505. 10: Chen JQ, Xie JH, Bao DH, Liu S, Zhou QL. Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization. Org Lett. 2012 Jun 1;14(11):2714-7. doi: 10.1021/ol300913g. Epub 2012 May 21. PubMed PMID: 22612349. 11: Chen P, Bao X, Zhang LF, Ding M, Han XJ, Li J, Zhang GB, Tu YQ, Fan CA. Asymmetric synthesis of bioactive hydrodibenzofuran alkaloids: (-)-lycoramine, (-)-galanthamine, and (+)-lunarine. Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8161-6. doi: 10.1002/anie.201103198. Epub 2011 Jul 11. PubMed PMID: 21748835. 12: Mu HM, Wang R, Li XD, Jiang YM, Peng F, Xia B. Alkaloid accumulation in different parts and ages of Lycoris chinensis. Z Naturforsch C. 2010 Jul-Aug;65(7-8):458-62. PubMed PMID: 20737914. 13: Ishikawa T, Kudo K, Kuroyabu K, Uchida S, Kudoh T, Saito S. Domino double Michael-Claisen cyclizations: a powerful general tool for introducing quaternary stereocenters at C4 of cyclohexane-1,3-diones and total synthesis of diverse families of sterically congested alkaloids. J Org Chem. 2008 Oct 3;73(19):7498-508. doi: 10.1021/jo801316s. Epub 2008 Sep 10. PubMed PMID: 18781800. 14: Malachowski WP, Paul T, Phounsavath S. The enantioselective synthesis of (-)-lycoramine with the Birch-Cope sequence. J Org Chem. 2007 Aug 31;72(18):6792-6. Epub 2007 Aug 4. PubMed PMID: 17676911. 15: Youssef DT, Frahm AW. Alkaloids of the flowers of Pancratium maritimum. Planta Med. 1998 Oct;64(7):669-70. PubMed PMID: 17253308. 16: Fan CA, Tu YQ, Song ZL, Zhang E, Shi L, Wang M, Wang B, Zhang SY. An efficient total synthesis of (+/-)-lycoramine. Org Lett. 2004 Dec 9;6(25):4691-4. PubMed PMID: 15575662. 17: Arisawa M, Tohma H, Kita Y. [Development of intramolecular oxidative phenolic coupling reactions using hypervalent iodine (III) reagents and their application to the synthesis of Amaryllidaceae alkaloids]. Yakugaku Zasshi. 2000 Oct;120(10):1061-73. Review. Japanese. PubMed PMID: 11082716. 18: Li HY, Ma GE, Xu Y, Hong SH. Alkaloids of Lycoris guangxiensis1. Planta Med. 1987 Jun;53(3):259-61. PubMed PMID: 17269013. 19: Misaka Y, Mizutani T, Sekido M, Uyeo S. The total synthesis of (+-)-lycoramine. II. J Chem Soc Perkin 1. 1968;23:2954-9. PubMed PMID: 5749970. 20: Hazama N, Irie H, Mizutani T, Shingu T, Takada M, Uyeo S, Yoshitake A. The total synthesis of (plus or minus)-lycoramine. I. J Chem Soc Perkin 1. 1968;23:2947-53. PubMed PMID: 5749969.