Gyromitrin | CAS#16568-02-8 | biochemical

MedKoo Cat#: 146338 | Name: Gyromitrin

Description:

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

Gyromitrin is a toxic compound found in certain species of false morel mushrooms, such as Gyromitra esculenta. Once ingested, gyromitrin is hydrolyzed in the body to monomethylhydrazine (MMH), a compound that interferes with vitamin B6-dependent enzymes, disrupting the synthesis of gamma-aminobutyric acid (GABA) and leading to neurotoxic effects such as seizures. It also causes liver and kidney damage due to its cytotoxic properties.

Chemical Structure

Gyromitrin

CAS#16568-02-8

Theoretical Analysis

MedKoo Cat#: 146338

Name: Gyromitrin

CAS#: 16568-02-8

Chemical Formula: C4H8N2O

Exact Mass: 100.0637

Molecular Weight: 100.12

Elemental Analysis: C, 47.99; H, 8.05; N, 27.98; O, 15.98

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Gyromitrin;

IUPAC/Chemical Name

(E)-N'-ethylidene-N-methylformohydrazide

InChi Key

IMAGWKUTFZRWSB-HWKANZROSA-N

InChi Code

1S/C4H8N2O/c1-3-5-6(2)4-7/h3-4H,1-2H3/b5-3+

SMILES Code

C\C=N\N(C)C=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 100.12 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: Dirks AC, Mohamed OG, Schultz PJ, Miller AN, Tripathi A, James TY. Not all bad: Gyromitrin has a limited distribution in the false morels as determined by a new ultra high-performance liquid chromatography method. Mycologia. 2023 Jan- Feb;115(1):1-15. doi: 10.1080/00275514.2022.2146473. Epub 2022 Dec 21. PMID: 36541902. 2: Vohra V, Dirks A, Bonito G, James T, Carroll DK. A 19-year longitudinal assessment of gyromitrin-containing (Gyromitra spp.) mushroom poisonings in Michigan. Toxicon. 2024 Aug 28;247:107825. doi: 10.1016/j.toxicon.2024.107825. Epub 2024 Jun 20. PMID: 38908526. 3: Lagrange E, Loriot MA, Chaudhary NK, Schultz P, Dirks AC, Guissart C, James TY, Vernoux JP, Camu W, Tripathi A, Spencer PS. Corrected speciation and gyromitrin content of false morels linked to ALS patients with mostly slow- acetylator phenotypes. eNeurologicalSci. 2024 May 4;35:100502. doi: 10.1016/j.ensci.2024.100502. PMID: 38770222; PMCID: PMC11103407. 4: Horowitz KM, Kong EL, Regina AC, Horowitz BZ. Gyromitra Mushroom Toxicity. 2024 Feb 9. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2025 Jan–. PMID: 29262102. 5: Gyromitrin (acetaldehyde formylmethylhydrazone). IARC Monogr Eval Carcinog Risk Chem Hum. 1983 Jul;31:163-70. PMID: 6579004. 6: Karlson-Stiber C, Persson H. Cytotoxic fungi--an overview. Toxicon. 2003 Sep 15;42(4):339-49. doi: 10.1016/s0041-0101(03)00238-1. PMID: 14505933. 7: Toth B, Patil K. Gyromitrin as a tumor inducer. Neoplasma. 1981;28(5):559-64. PMID: 7198186. 8: Braun R, Dittmar W, Greeff U. Considerations on the carcinogenicity of the mushroom poison gyromitrin and its metabolites. J Appl Toxicol. 1981 Oct;1(5):243-6. doi: 10.1002/jat.2550010502. PMID: 6892244. 9: Bergman K, Hellenäs KE. Methylation of rat and mouse DNA by the mushroom poison gyromitrin and its metabolite monomethylhydrazine. Cancer Lett. 1992 Jan 10;61(2):165-70. doi: 10.1016/0304-3835(92)90175-u. PMID: 1730140. 10: List PH, Luft P. Gyromitrin, das Gift der Frühjahrslorchel. 16. Uber Pilzinhaltsstoffe [Gyromitrin, the poison of Gyromitra esculenta. 16. On the fungi contents]. Arch Pharm Ber Dtsch Pharm Ges. 1968 Apr;301(4):294-305. German. doi: 10.1002/ardp.19683010410. PMID: 5244383. 11: Tuğcan MO, Akpınar AA. Mushroom poisoning: An updated review. Turk J Emerg Med. 2025 Jan 2;25(1):10-16. doi: 10.4103/tjem.tjem_129_24. PMID: 39882097; PMCID: PMC11774429. 12: von Wright A, Niskanen A, Pyysalo H. Mutagenic properties of ethylidene gyromitrin and its metabolites in microsomal activation tests and in the host- mediated assay. Mutat Res. 1978 Oct;54(2):167-73. doi: 10.1016/0165-1161(78)90037-7. PMID: 362188. 13: Pyysalo H. Tests for gyromitrin, a poisonous compound in false morel gyromitra esculenta. Z Lebensm Unters Forsch. 1976;160(3):325-30. doi: 10.1007/BF01132299. PMID: 983341. 14: Gouvinhas I, Silva J, Alves MJ, Garcia J. The most dreadful mushroom toxins: a review of their toxicological mechanisms, chemical structural characteristics, and treatment. EXCLI J. 2024 May 28;23:833-859. doi: 10.17179/excli2024-7257. PMID: 39165585; PMCID: PMC11333700. 15: Lagrange E, Vernoux JP. Warning on False or True Morels and Button Mushrooms with Potential Toxicity Linked to Hydrazinic Toxins: An Update. Toxins (Basel). 2020 Jul 29;12(8):482. doi: 10.3390/toxins12080482. Erratum in: Toxins (Basel). 2022 May 16;14(5):345. doi: 10.3390/toxins14050345. PMID: 32751277; PMCID: PMC7472412. 16: Braun R, Kremer J, Rau H. Renal functional response to the mushroom poison gyromitrin. Toxicology. 1979 Jun-Jul;13(2):187-96. PMID: 42171. 17: von der Hude W, Braun R. On the mutagenicity of metabolites derived from the mushroom poison gyromitrin. Toxicology. 1983 Feb;26(2):155-60. doi: 10.1016/0300-483x(83)90066-5. PMID: 6344333. 18: Braun R, Greeff U, Netter KJ. Liver injury by the false morel poison gyromitrin. Toxicology. 1979 Feb;12(2):155-63. doi: 10.1016/0300-483x(79)90042-8. PMID: 473232. 19: Arshadi M, Nilsson C, Magnusson B. Gas chromatography-mass spectrometry determination of the pentafluorobenzoyl derivative of methylhydrazine in false morel (Gyromitra esculenta) as a monitor for the content of the toxin gyromitrin. J Chromatogr A. 2006 Sep 1;1125(2):229-33. doi: 10.1016/j.chroma.2006.05.040. Epub 2006 Jun 19. PMID: 16782115. 20: Mäkinen SM, Kreula M, Kauppi M. Acute oral toxicity of ethylidene gyromitrin in rabbits, rats and chickens. Food Cosmet Toxicol. 1977 Dec;15(6):575-8. doi: 10.1016/0015-6264(77)90072-4. PMID: 604233.