CHEBI:16737 - creatinine

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ChEBI Name creatinine ChEBI ID CHEBI:16737 Definition A lactam obtained by formal cyclocondensation of creatine. It is a metabolite of creatine. Stars This entity has been manually annotated by the ChEBI Team. Secondary ChEBI IDs CHEBI:14029, CHEBI:3910, CHEBI:23406 Supplier Information ZINC000008214766 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and Duboisia hopwoodii) and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits (nAChRα9 and nAChRα10) where it acts as a receptor antagonist. Nicotine constitutes approximately 0.6–3.0% of the dry weight of tobacco. Nicotine is also present at ppb concentrations in edible plants in the family Solanaceae, including potatoes, tomatoes, and eggplants, though sources disagree on whether this has any biological significance to human consumers. It functions as an antiherbivore toxin; consequently, nicotine was widely used as an insecticide in the past, and neonicotinoids (structurally similar to nicotine), such as imidacloprid, are some of the most effective and widely used insecticides. Nicotine is highly addictive. Slow-release forms (gums and patches, when used correctly) can be less addictive and help in quitting. Animal research suggests that monoamine oxidase inhibitors present in tobacco smoke may enhance nicotine's addictive properties. An average cigarette yields about 2 mg of absorbed nicotine. The estimated lower dose limit for fatal outcomes is 500–1,000 mg of ingested nicotine for an adult (6.5–13 mg/kg). Nicotine addiction involves drug-reinforced behavior, compulsive use, and relapse following abstinence. Nicotine dependence involves tolerance, sensitization, physical dependence, and psychological dependence, which can cause distress. Nicotine withdrawal symptoms include depression, stress, anxiety, irritability, difficulty concentrating, and sleep disturbances. Mild nicotine withdrawal symptoms are measurable in unrestricted smokers, who experience normal moods only as their blood nicotine levels peak, with each cigarette. On quitting, withdrawal symptoms worsen sharply, then gradually improve to a normal state. Nicotine use as a tool for quitting smoking has a good safety history. Animal studies suggest that nicotine may adversely affect cognitive development in adolescence, but the relevance of these findings to human brain development is disputed. At low amounts, it has a mild analgesic effect. According to the International Agency for Research on Cancer, "nicotine is not generally considered to be a carcinogen". The Surgeon General of the United States indicates that evidence is inadequate to infer the presence or absence of a causal relationship between exposure to nicotine and risk for cancer. Nicotine has been shown to produce birth defects in humans and is considered a teratogen. The median lethal dose of nicotine in humans is unknown. High doses are known to cause nicotine poisoning, organ failure, and death through paralysis of respiratory muscles, though serious or fatal overdoses are rare. Read full article at Wikipedia Formula C4H7N3O Net Charge 0 Average Mass 113.11800 Monoisotopic Mass 113.05891 InChI InChI=1S/C4H7N3O/c1-7-2-3(8)6-4(7)5/h2H2,1H3,(H2,5,6,8) InChIKey DDRJAANPRJIHGJ-UHFFFAOYSA-N SMILES CN1CC(=O)NC1=N Metabolite of Species Details Mus musculus (NCBI:txid10090) See: PubMed Homo sapiens (NCBI:txid9606) See: DOI Roles Classification Biological Role(s): human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). Application(s): diagnostic agent A substance administered to aid diagnosis of a disease. View more via ChEBI Ontology ChEBI Ontology Outgoing creatinine (CHEBI:16737) has functional parent creatine (CHEBI:16919) creatinine (CHEBI:16737) has role diagnostic agent (CHEBI:33295) creatinine (CHEBI:16737) has role human metabolite (CHEBI:77746) creatinine (CHEBI:16737) is a imidazolidinone (CHEBI:55370) creatinine (CHEBI:16737) is a lactam (CHEBI:24995) IUPAC Name 2-imino-1-methylimidazolidin-4-one Synonyms Sources 1-methylglycocyamidine ChEBI 1-Methylglycocyamidine KEGG COMPOUND 1-Methylhydantoin-2-imide HMDB 2-amino-1,5-dihydro-1-methyl-4H-Imidazol-4-one HMDB 2-Amino-1-methylimidazolin-4-one HMDB Creatine anhydride HMDB creatinina ChEBI Creatinine KEGG COMPOUND creatinine UniProt créatinine ChEBI Kreatinin ChEBI Manual Xrefs Databases C00791 KEGG COMPOUND Creatinine Wikipedia CREATININE MetaCyc D03600 KEGG DRUG HMDB0000562 HMDB View more database links Registry Numbers Types Sources 112064 Reaxys Registry Number Reaxys 60-27-5 CAS Registry Number ChemIDplus 60-27-5 CAS Registry Number NIST Chemistry WebBook Citations Types Sources 11256540 PubMed citation Europe PMC 11981083 PubMed citation Europe PMC 17190852 PubMed citation Europe PMC 17422601 PubMed citation Europe PMC 18182718 PubMed citation Europe PMC 19236048 PubMed citation Europe PMC 19715855 PubMed citation Europe PMC 19968328 PubMed citation Europe PMC 21775764 PubMed citation Europe PMC 22047975 PubMed citation Europe PMC 22121923 PubMed citation Europe PMC 22166252 PubMed citation Europe PMC 22207347 PubMed citation Europe PMC 22212624 PubMed citation Europe PMC 22223530 PubMed citation Europe PMC 22331238 PubMed citation Europe PMC 22338083 PubMed citation Europe PMC 22349552 PubMed citation Europe PMC 22390548 PubMed citation Europe PMC 22432114 PubMed citation Europe PMC 22441184 PubMed citation Europe PMC 22459582 PubMed citation Europe PMC 22498455 PubMed citation Europe PMC Last Modified 23 October 2015