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gyromitrin
N-methyl-N-formyl hydrazone of acetaldehyde

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Name:	N-[(E)-ethylideneamino]-N-methylformamide
CAS Number:	16568-02-8	3D/inchi
Other(deleted CASRN):	69349-96-8
FDA UNII:	S9J72G0T46
Beilstein Number:	1922396
XlogP3-AA:	-0.30 (est)
Molecular Weight:	100.12096000
Formula:	C4 H8 N2 O
BioActivity Summary:	listing
NMR Predictor:	Predict (works with chrome, Edge or firefox)

Category:natural substances and extractives

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:	Search
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NCBI:	Search

Physical Properties:

Appearance:	colorless to pale yellow clear liquid (est)
Assay:	95.00 to 100.00
Food Chemicals Codex Listed:	No
Boiling Point:	135.80 °C. @ 760.00 mm Hg (est)
Vapor Pressure:	7.600000 mmHg @ 25.00 °C. (est)
Flash Point:	97.00 °F. TCC ( 36.00 °C. ) (est)
logP (o/w):	-0.300 (est)
Soluble in:
	water, 3.608e+005 mg/L @ 25 °C (est)

Organoleptic Properties:

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

None found

Safety Information:


Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
unreported-child LDLo 10 mg/kg Mitteilungen aus dem Gebiete der Lebensmitteluntersuchung und Hygiene. Vol. 65, Pg. 453, 1974. unreported-human LDLo 20 mg/kg Mitteilungen aus dem Gebiete der Lebensmitteluntersuchung und Hygiene. Vol. 65, Pg. 453, 1974. oral-mouse LD50 344 mg/kg Mutation Research. Vol. 54, Pg. 167, 1978. oral-rabbit LD50 50 mg/kg Naturwissenschaften. Vol. 62, Pg. 395, 1975. oral-rat LD50 320 mg/kg BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Food and Cosmetics Toxicology. Vol. 15, Pg. 575, 1977.
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for gyromitrin usage levels up to:
	not for fragrance use.

Recommendation for gyromitrin flavor usage levels up to:
	not for flavor use.

Safety References:

EPI System: View

Chemical Carcinogenesis Research Information System:Search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

Carcinogenic Potency Database:Search

EPA GENetic TOXicology:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :9548611

National Institute of Allergy and Infectious Diseases:Data

N-[(E)-ethylideneamino]-N-methylformamide

Chemidplus:0016568028

References:

	N-[(E)-ethylideneamino]-N-methylformamide
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	9548611
Pubchem (sid):	134993450

Other Information:

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
CHEBI:	View
KEGG (GenomeNet):	C08305
HMDB (The Human Metabolome Database):	HMDB33952
FooDB:	FDB012167
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View

Potential Blenders and core components note

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):note

gyromitra esculenta
Search Trop Picture

Synonyms:

	acetaldehyde formylmethylhydrazone
	acetaldehyde methyl formyl hydrazone
	acetaldehyde methylformylhydrazone
	acetaldehyde N-methyl-N-formylhydrazone
	acetaldehyde N-methylformylhydrazone
	acetaldehyde-N-formyl-N-methylhydrazone
	acetaldehyde-N-methyl-N-formylhydrazone
	acetaldehyde, N-formyl-N-methylhydrazone
	acetylaldehyde-N-methyl-N-formylhydrazone
N-[(E)-	ethylideneamino]-N-methylformamide
	formic acid, 2-ethylidene-1-methylhydrazide
	formic acid, ethylidenemethylhydrazide
	hydrazine carboxaldehyde, ethylidenemethyl-
	hydrazine carboxyaldehyde, ethylidenemethyl-
	hydrazinecarboxaldehyde, ethylidenemethyl-
N-	methyl-N-formyl hydrazone of acetaldehyde

Articles:

PubMed:[Mushroom poisonings that we don't think about: Gyromitra poisoning].

PubMed: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.

PubMed:The epidemiology, toxidromic classification, general management, and prevention of mushroom poisoning in the United States.

PubMed:[Acute higher funghi mushroom poisoning and its treatment].

PubMed:Cytotoxic fungi--an overview.

PubMed:Clinical approach to toxic mushroom ingestion.

PubMed:Methylation of rat and mouse DNA by the mushroom poison gyromitrin and its metabolite monomethylhydrazine.

PubMed:Poisoning by Gyromitra esculenta--a review.

PubMed:[Poisoning by Geromitra esculenta].

PubMed:[Diagnosis and therapy of mushroom poisoning (II)].

PubMed:Un fleur du mal--gyromitrin poisoning.

PubMed:N-methyl-N-formylhydrazine: a toxic and mutagenic inhibitor of the intestinal diamine oxidase.

PubMed:Methylation of deoxyribonucleic acid in the rat by the mushroom poison gyromitrin.

PubMed:Gyromitrin (acetaldehyde formylmethylhydrazone).

PubMed:On the mutagenicity of metabolites derived from the mushroom poison gyromitrin.

PubMed:Poisoning by Gyromitra : a possible mechanism.

PubMed:[Influence of the mushroom poison gyromitrin on the lipids of rat liver (author's transl)].

PubMed:The toxicology of 1-acetyl-2-methyl-2-formyl hydrazine (Ac-MFH).

PubMed:Cancer induction in mice with acetaldehyde methylformylhydrazone of the false morel mushroom.

PubMed:Considerations on the carcinogenicity of the mushroom poison gyromitrin and its metabolites.

PubMed:Gyromitrin as a tumor inducer.

PubMed:Indications for nitrosamide formation from the mushroom poison gyromitrin by rat liver microsomes.

PubMed:The importance of human intestinal diamine oxidase in the oxidation of histamine and/or putrescine.

PubMed:Renal functional response to the mushroom poison gyromitrin.

PubMed:Liver injury by the false morel poison gyromitrin.

PubMed:[Acute poisoning by Gyromitra esculenta (author's transl)].

PubMed:Mutagenic properties of ethylidene gyromitrin and its metabolites in microsomal activation tests and in the host-mediated assay.

PubMed:Acute oral toxicity of ethylidene gyromitrin in rabbits, rats and chickens.

PubMed:Formation of methylhydrazine from acetaldehyde N-methyl-N-formylhydrazone, a component of Gyromitra esculenta.

PubMed:Short-term peroral toxicity of ethylidene gyromitrin in rabbits and chickens.

PubMed:Tests for gyromitrin, a poisonous compound in false morel gyromitra esculenta.

PubMed:[Detection and content determination of gyromitrin in fresh Gyromitra esculenta. 19. Mushroom contents].

PubMed:[Gyromitrin, the poison of Gyromitra esculenta. 16. On the fungi contents].

Notes:

isolated from edible mushroom gyromitra (helvella) esculenta; inhalation hallucinogen; highly toxic. Toxin from the fungus Gyromitra esculenta. Freq. cause of mushroom poisoning Gyromitrin is a toxin and possible carcinogen present in most members of the fungal genus Gyromitra, most notably the false morel G. esculenta.

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