Grayanotoxin III | 4678-45-9 | neurotoxin

MedKoo Cat#: 581549 | Name: Grayanotoxin III

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Description:

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

Grayanotoxins are a group of closely related neurotoxins named after Leucothoe grayana, a plant native to Japan originally. Extract from leaves Leucothoe grayana (Ericaceae).

Chemical Structure

Grayanotoxin III

CAS#4678-45-9

Theoretical Analysis

MedKoo Cat#: 581549

Name: Grayanotoxin III

CAS#: 4678-45-9

Chemical Formula: 20H34O6

Exact Mass: 370.2355

Molecular Weight: 370.49

Elemental Analysis: C, 64.84; H, 9.25; O, 25.91

Price and Availability

Size	Price	Availability	Quantity
100µg	USD 750.00	2 Weeks

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Related CAS #

No Data

Synonym

Grayanotoxin III; Deacetylandromedotoxin; Deacylasebotoxin I; Andromedol

IUPAC/Chemical Name

(3beta,6beta,14R)-Grayanotoxane-3,5,6,10,14,16-hexol

InChi Key

BWMFRQKICHXLSH-FIRPSQKQSA-N

InChi Code

InChI=1S/C20H34O6/c1-16(2)13(21)7-12-18(4,25)11-6-5-10-15(23)19(11,9-17(10,3)24)8-14(22)20(12,16)26/h10-15,21-26H,5-9H2,1-4H3/t10-,11+,12+,13+,14-,15-,17-,18-,19+,20+/m1/s1

SMILES Code

[H][C@@]12C[C@H](O)C(C)([C@@]1(O)[C@H](O)C[C@@]34C[C@]([C@H](CC[C@]4([C@]2(O)C)[H])[C@H]3O)(O)C)C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 370.49 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

1: Hwang T, Noh E, Jeong JH, Park SK, Shin D, Kang H. Determination of Grayanotoxins from Rhododendron brachycarpum in Dietary Supplements and Homemade Wine by Liquid Chromatography-Quadrupole Time-of-Flight-Mass Spectrometry and Liquid Chromatography-Tandem Mass Spectrometry. J Agric Food Chem. 2018 Feb 28;66(8):1935-1940. doi: 10.1021/acs.jafc.7b05054. Epub 2018 Feb 20. PubMed PMID: 29433311. 2: Choi HL, Park KH, Park JS, Choi HY, Kim H, Kim SM. Relationship between blood toxin level and clinical features in patients with grayanotoxin poisoning - six clinical cases. Clin Toxicol (Phila). 2017 Nov;55(9):991-995. doi: 10.1080/15563650.2017.1331448. Epub 2017 Jun 8. PubMed PMID: 28594250. 3: Lim MY, Phua DH, Ooi CK. Heart stopping honey-not just Turkish honey. Am J Emerg Med. 2016 Sep;34(9):1915.e1-3. doi: 10.1016/j.ajem.2016.02.014. Epub 2016 Feb 13. PubMed PMID: 26947374. 4: Aygun A, Gunduz A, Turedi S, Turkmen S, Karaca Y, Ayaz FA, Ahn SY, Kim S. Examination using LC-MS/MS determination of grayanotoxin levels in blood, urine, and honey consumed by patients presenting to the emergency department with mad honey intoxication and relations with clinical data: a preliminary study. Ann Saudi Med. 2015 Mar-Apr;35(2):161-4. doi: 10.5144/0256-4947.2015.161. PubMed PMID: 26336024; PubMed Central PMCID: PMC6074137. 5: Sahin H, Yildiz O, Kolayli S. Effects of Mad Honey on Some Biochemical Parameters in Rats. J Evid Based Complementary Altern Med. 2016 Oct;21(4):255-9. doi: 10.1177/2156587215596430. Epub 2015 Aug 2. PubMed PMID: 26239637. 6: Sibel S, Enis YM, Hüseyin S, Timucin AA, Duran O. Analysis of grayanatoxin in Rhododendron honey and effect on antioxidant parameters in rats. J Ethnopharmacol. 2014 Oct 28;156:155-61. doi: 10.1016/j.jep.2014.08.027. Epub 2014 Sep 3. PubMed PMID: 25193682. 7: Kaplan M, Olgun EO, Karaoglu O. Determination of grayanotoxins in honey by liquid chromatography tandem mass spectrometry using dilute-and-shoot sample preparation approach. J Agric Food Chem. 2014 Jun 18;62(24):5485-91. doi: 10.1021/jf501560t. Epub 2014 Jun 9. PubMed PMID: 24882375. 8: Kurtoglu AB, Yavuz R, Evrendilek GA. Characterisation and fate of grayanatoxins in mad honey produced from Rhododendron ponticum nectar. Food Chem. 2014 Oct 15;161:47-52. doi: 10.1016/j.foodchem.2014.03.127. Epub 2014 Apr 4. PubMed PMID: 24837920. 9: Cho HE, Ahn SY, Kim DW, Woo SH, Park SH, Hwang K, Moon DC, Kim S. Development of a liquid chromatography-tandem mass spectrometry method for the determination of Grayanotoxins in rat blood and its application to toxicokinetic study. Biomed Chromatogr. 2014 Dec;28(12):1624-32. doi: 10.1002/bmc.3190. Epub 2014 Apr 30. PubMed PMID: 24782399. 10: Chen SP, Lam YH, Ng VC, Lau FL, Sze YC, Chan WT, Mak TW. Mad honey poisoning mimicking acute myocardial infarction. Hong Kong Med J. 2013 Aug;19(4):354-6. doi: 10.12809/hkmj133936. PubMed PMID: 23918513. 11: Durdagi S, Scozzafava G, Vullo D, Sahin H, Kolayli S, Supuran CT. Inhibition of mammalian carbonic anhydrases I-XIV with grayanotoxin III: solution and in silico studies. J Enzyme Inhib Med Chem. 2014 Aug;29(4):469-75. doi: 10.3109/14756366.2013.804072. Epub 2013 Aug 5. PubMed PMID: 23914927. 12: Hough RL, Crews C, White D, Driffield M, Campbell CD, Maltin C. Degradation of yew, ragwort and rhododendron toxins during composting. Sci Total Environ. 2010 Sep 1;408(19):4128-37. doi: 10.1016/j.scitotenv.2010.05.024. Epub 2010 Jun 25. PubMed PMID: 20579691. 13: Kim SE, Shin MC, Akaike N, Kim CJ. Presynaptic effects of grayanotoxin III on excitatory and inhibitory nerve terminals in rat ventromedial hypothalamic neurons. Neurotoxicology. 2010 Mar;31(2):230-8. doi: 10.1016/j.neuro.2009.12.006. Epub 2009 Dec 28. PubMed PMID: 20038438. 14: Holstege DM, Puschner B, Le T. Determination of grayanotoxins in biological samples by LC-MS/MS. J Agric Food Chem. 2001 Mar;49(3):1648-51. PubMed PMID: 11312909. 15: Terai T, Araho D, Osakabe K, Katai M, Narama I, Matsuura T, Katakawa J, Tetsumi T, Sato M. Isolation of iso-grayanotoxin II from leaves of Leucothoe grayana Max. Its X-ray crystallographic analysis and acute toxicity in mice. Chem Pharm Bull (Tokyo). 2000 Jan;48(1):142-4. PubMed PMID: 10705491. 16: Terai T, Sato M, Narama I, Matuura T, Katakawa J, Tetsumi M. Transformation of grayanotoxin III to 10-epi-grayanotoxin III. Its X-ray crystallographic analysis and acute toxicity in mice. Chem Pharm Bull (Tokyo). 1996 Jun;44(6):1245-7. PubMed PMID: 8814955. 17: Plumlee KH, VanAlstine WG, Sullivan JM. Japanese pieris toxicosis of goats. J Vet Diagn Invest. 1992 Jul;4(3):363-4. PubMed PMID: 1515506. 18: Yavuz H, Ozel A, Akkus I, Erkul I. Honey poisoning in Turkey. Lancet. 1991 Mar 30;337(8744):789-90. PubMed PMID: 1672407. 19: Nishikawa Y, Fukumoto K, Tetsumi T, Katai M, Meguri H. [Effects of grayanotoxin III on liver function and renal function in rats]. Yakugaku Zasshi. 1989 May;109(5):340-3. Japanese. PubMed PMID: 2625664. 20: Ohgaki T, Uchida S, Meguri H, Ogita K, Yoneda Y. Preventive action of quisqualic acid against grayanotoxin-induced suppression of locomotor activity in mice. Neuropharmacology. 1988 Oct;27(10):1045-53. PubMed PMID: 3070432.