Gyromitrin

Gyromitrin is a volatile derivative of hydrazine (see Figure 4) with the chemical formula of acetaldehyde methyl formylhydrazone and is readily converted to N-methyl-N-formyl hydrazine and N-methylhydrazine. It is primarily a liver toxin although the red blood cells and central nervous system are also involved. The 

Figure 4. Gyromitrin, toxin of the False Morel mushroom.

The structure of gyromitrine was found to be acetaldehyde iV-methyl-iV-formylhydrazone on the basis of spectral analysis and chemical transformations. On acidic hydrolysis gyromitrine was converted to monomethyl-hydrazine 343), also a natural constituent of G. esculenta 344,345), which is the highly toxic substance used as rocket fuel to help send Apollo 

Common Name(s) Brown Bonnet Poison Gyromitrin 

Common Name(s) Walnut Morel Poison Gyromitrin 

Common Name(s) Red False Morel Poison Gyromitrin 

Common Name(s) Beefsteak Morel Poison Gyromitrin 

Formyl-hydrazino)-4-(5-nitro-2-furyl) thiazole Furan Gyromitrin Flexachlorobenzene Flexachloroethane Flexamethyl phosphoramide Hydrazine Hydrazine sulfate Hydrazobenzene Indeno [1,2,3-cd] pyrene Isoprene Lead (II) acetate Lead chromate Lead phosphate Lindane (and other hexachlorocyclohexane isomers) 

Common Name(s) Snow Mushroom, Snow-Bank Morel Poison Gyromitrin 

SYNS ACETALDEHYDE-N-FORMYI N-METHYL-HYDRAZONE ETHYLIDENE GYROMITRIN GYROAOTRIN N-METHYL-N-FORMYL HYDRA-ZONE of ACETALDEHYDE 

The absorption rate is not known. Symptoms typically occur after a latent period of 6-24 h after ingestion of the mushroom. Gyromitrin is converted to methylformylhydrazine (MFH) and then to monomethylhydrazine (MMH). Some MFH is also converted to nitrosamide, which causes liver tumors in experimental animals. 

Enol imines have also been generated and characterized by NRMS. For example, AT-methylformimidic acid, CH3-N=CH-OH (8) was obtained by neutralization of cation-radical 8+, which was generated by dissociative ionization of gyromitrin, CH3CH=N-N(CH3)CH=0 [72]. 

The direct insertion of plant material into the mass spectrometer can give useful information on the constituents present, provided that sufficient data have already been accumulated from synthetic compounds and from conventional phytochemistry. Direct mass spectral analysis (MIKES) of whole freeze-dried mushrooms (Helvella esculenta) indicates the presence of gyromitrin (21 = 

---