Guanidine

Not to be confused with Guanine, Guanosine, or Guanfacine.
Guanidine
Skeletal formula of guanidine
Skeletal formula of guanidine
Skeletal formula of guanidine with the implicit carbon shown, and all explicit hydrogens added.
Skeletal formula of guanidine with the implicit carbon shown, and all explicit hydrogens added.
Ball and stick model of guanidine
Ball and stick model of guanidine
Spacefill model of guanidine
Spacefill model of guanidine
Names
Preferred IUPAC name
Guanidine[1]
Other names
Iminomethanediamine
Identifiers
3D model (JSmol)
506044
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.656 Edit this at Wikidata
EC Number
  • 204-021-8
100679
MeSH Guanidine
UNII
  • InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4) checkY
    Key: ZRALSGWEFCBTJO-UHFFFAOYSA-N checkY
  • NC(N)=N
Properties
CH5N3
Molar mass 59.072 g·mol−1
Melting point 50 °C (122 °F; 323 K)
log P −1.251
Basicity (pKb) 0.4[2]
Conjugate acid Guanidinium
Thermochemistry
−57 – −55 kJ mol−1
−1.0511 – −1.0531 MJ mol−1
Pharmacology
Pharmacokinetics:
7–8 hours
Hazards
Lethal dose or concentration (LD, LC):
475 mg/kg (oral, rat)[3]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Guanidine is the compound with the formula HNC(NH2)2. It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine predominantly in patients experiencing renal failure.[4] A guanidine moiety also appears in larger organic molecules, including on the side chain of arginine.

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 883. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Cite error: The named reference Perrin was invoked but never defined (see the help page).
  3. ^ "Guanidine hydrochloride". ChemIDplus. National Library of Medicine. Archived from the original on 2014-08-12. Retrieved 2014-08-10.
  4. ^ Sawynok J, Dawborn JK (1975). "Plasma concentration and urinary excretion of guanidine derivatives in normal subjects and patients with renal failure". Clinical and Experimental Pharmacology & Physiology. 2 (1): 1–15. doi:10.1111/j.1440-1681.1975.tb02368.x. PMID 1126056. S2CID 41794868.