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MedKoo Cat#: 530265 | Name: Ungeremine acetate

Description:

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

Ungeremine, also known as AT-1840, is a betaine-type alkaloid isolated from Nerine bowdenii and related plants such as Pancratium maritimum. Pharmacologically, it is of interest as an acetylcholinesterase inhibitor and accordingly as possibly relevant to Alzheimer's disease. It also has been investigated as a bactericide.

Chemical Structure

Ungeremine acetate
Ungeremine acetate
CAS#61221-41-8 (acetate)

Theoretical Analysis

MedKoo Cat#: 530265

Name: Ungeremine acetate

CAS#: 61221-41-8 (acetate)

Chemical Formula: C18H15NO5

Exact Mass: 266.0812

Molecular Weight: 325.32

Elemental Analysis: C, 66.46; H, 4.65; N, 4.31; O, 24.59

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 #
97438-92-1 (inner salt) 2121-12-2 (cation) 2121-12-2 (chloride) 61221-41-8 (acetate) 21326-01-2 (nitrate) 2121-15-5 (bromide)
Synonym
AT-1840; AT 1840; AT1840; Ungeremine acetate; Lycobetaine acetate;
IUPAC/Chemical Name
(1,3)Dioxolo(4,5-j)pyrrolo(3,2,1-de)phenanthridinium, 4,5-dihydro-2-hydroxy-, acetate
InChi Key
HKIJKEFVQKXWGW-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H11NO3.C2H4O2/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17;1-2(3)4/h3-7H,1-2,8H2;1H3,(H,3,4)
SMILES Code
OC1=CC2=C([N+]3=CC4=CC5=C(OCO5)C=C42)C(CC3)=C1.CC([O-])=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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 325.32 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: Moeini A, Cimmino A, Dal Poggetto G, Di Biase M, Evidente A, Masi M, Lavermicocca P, Valerio F, Leone A, Santagata G, Malinconico M. Effect of pH and TPP concentration on chemico-physical properties, release kinetics and antifungal activity of Chitosan-TPP-Ungeremine microbeads. Carbohydr Polym. 2018 Sep 1;195:631-641. doi: 10.1016/j.carbpol.2018.05.005. Epub 2018 May 4. PubMed PMID: 29805021. 2: Valerio F, Masi M, Cimmino A, Moeini SA, Lavermicocca P, Evidente A. Antimould microbial and plant metabolites with potential use in intelligent food packaging. Nat Prod Res. 2018 Jul;32(13):1605-1610. doi: 10.1080/14786419.2017.1385018. Epub 2017 Oct 13. PubMed PMID: 29027475. 3: Chen T, Gong T, Zhao T, Fu Y, Zhang Z, Gong T. A comparison study between lycobetaine-loaded nanoemulsion and liposome using nRGD as therapeutic adjuvant for lung cancer therapy. Eur J Pharm Sci. 2018 Jan 1;111:293-302. doi: 10.1016/j.ejps.2017.09.041. Epub 2017 Sep 28. PubMed PMID: 28966099. 4: Chen T, Song X, Gong T, Fu Y, Yang L, Zhang Z, Gong T. nRGD modified lycobetaine and octreotide combination delivery system to overcome multiple barriers and enhance anti-glioma efficacy. Colloids Surf B Biointerfaces. 2017 Aug 1;156:330-339. doi: 10.1016/j.colsurfb.2017.05.038. Epub 2017 May 15. PubMed PMID: 28544965. 5: Chen T, Li W, Gong T, Fu Y, Ding R, Gong T, Zhang Z. Analysis of Lycobetaine in Rat Plasma by LC-ESI-MS/MS. J Chromatogr Sci. 2017 Mar 1;55(3):301-308. doi: 10.1093/chromsci/bmw185. PubMed PMID: 27903551. 6: Liu ZM, Huang XY, Cui MR, Zhang XD, Chen Z, Yang BS, Zhao XK. Amaryllidaceae alkaloids from the bulbs of Lycoris radiata with cytotoxic and anti-inflammatory activities. Fitoterapia. 2015 Mar;101:188-93. doi: 10.1016/j.fitote.2015.01.003. Epub 2015 Jan 14. PubMed PMID: 25596094. 7: Liu XM, Wang L, Yin ZQ, Zhang SY, Ouyang S, Ye WC. [Alkaloids from bulbs of Lycoris radiata]. Zhongguo Zhong Yao Za Zhi. 2013 Apr;38(8):1188-92. Chinese. PubMed PMID: 23944033. 8: Zhao H, Lu H, Gong T, Zhang Z. Nanoemulsion loaded with lycobetaine-oleic acid ionic complex: physicochemical characteristics, in vitro, in vivo evaluation, and antitumor activity. Int J Nanomedicine. 2013;8:1959-73. doi: 10.2147/IJN.S43892. Epub 2013 May 21. PubMed PMID: 23723698; PubMed Central PMCID: PMC3666662. 9: 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. 10: Schrader KK, Avolio F, Andolfi A, Cimmino A, Evidente A. Ungeremine and Its hemisynthesized analogues as bactericides against Flavobacterium columnare. J Agric Food Chem. 2013 Feb 13;61(6):1179-83. doi: 10.1021/jf304586j. Epub 2013 Jan 30. PubMed PMID: 23331165. 11: Baechler SA, Fehr M, Habermeyer M, Hofmann A, Merz KH, Fiebig HH, Marko D, Eisenbrand G. Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs. Bioorg Med Chem. 2013 Feb 1;21(3):814-23. doi: 10.1016/j.bmc.2012.11.011. Epub 2012 Nov 26. PubMed PMID: 23266176. 12: Jahn S, Seiwert B, Kretzing S, Abraham G, Regenthal R, Karst U. Metabolic studies of the Amaryllidaceous alkaloids galantamine and lycorine based on electrochemical simulation in addition to in vivo and in vitro models. Anal Chim Acta. 2012 Dec 5;756:60-72. doi: 10.1016/j.aca.2012.10.042. Epub 2012 Nov 1. PubMed PMID: 23176740. 13: Casu L, Cottiglia F, Leonti M, De Logu A, Agus E, Tse-Dinh YC, Lombardo V, Sissi C. Ungeremine effectively targets mammalian as well as bacterial type I and type II topoisomerases. Bioorg Med Chem Lett. 2011 Dec 1;21(23):7041-4. doi: 10.1016/j.bmcl.2011.09.097. Epub 2011 Oct 1. PubMed PMID: 22014547; PubMed Central PMCID: PMC4551395. 14: Schrader KK, Andolfi A, Cantrell CL, Cimmino A, Duke SO, Osbrink W, Wedge DE, Evidente A. A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management. Chem Biodivers. 2010 Sep;7(9):2261-80. doi: 10.1002/cbdv.201000041. PubMed PMID: 20860028. 15: Evidente A, Kireev AS, Jenkins AR, Romero AE, Steelant WF, Van Slambrouck S, Kornienko A. Biological evaluation of structurally diverse amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. Planta Med. 2009 Apr;75(5):501-7. doi: 10.1055/s-0029-1185340. Epub 2009 Feb 23. PubMed PMID: 19235683; PubMed Central PMCID: PMC3125136. 16: Berkov S, Codina C, Viladomat F, Bastida J. Alkaloids from Galanthus nivalis. Phytochemistry. 2007 Jul;68(13):1791-8. Epub 2007 May 1. PubMed PMID: 17475295. 17: Pettit GR, Meng Y, Herald DL, Knight JC, Day JF. Antineoplastic agents. 553. The Texas grasshopper Brachystola magna. J Nat Prod. 2005 Aug;68(8):1256-8. PubMed PMID: 16124772; PubMed Central PMCID: PMC3251507. 18: Rhee IK, Appels N, Hofte B, Karabatak B, Erkelens C, Stark LM, Flippin LA, Verpoorte R. Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system. Biol Pharm Bull. 2004 Nov;27(11):1804-9. PubMed PMID: 15516727. 19: Barthelmes HU, Niederberger E, Roth T, Schulte K, Tang WC, Boege F, Fiebig HH, Eisenbrand G, Marko D. Lycobetaine acts as a selective topoisomerase II beta poison and inhibits the growth of human tumour cells. Br J Cancer. 2001 Nov 16;85(10):1585-91. PubMed PMID: 11720449; PubMed Central PMCID: PMC2363954. 20: Stark LM, Lin XF, Flippin LA. Total synthesis of Amaryllidaceae pyrrolophenanthridinium alkaloids via the Ziegler-Ullmann reaction: tortuosine, criasbetaine, and ungeremine. J Org Chem. 2000 May 19;65(10):3227-30. PubMed PMID: 10814221.