Guanidine

Guanidine
Skeletal formula of guanidine	Skeletal formula of guanidine with the implicit carbon shown, and all explicit hydrogens added.
Ball and stick model of guanidine	Spacefill model of guanidine
Names
	Preferred IUPAC name Guanidine
	Other names Iminomethanediamine
Identifiers
CAS Number	113-00-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	506044
ChEBI	CHEBI:42820 ;
ChEMBL	ChEMBL821 ;
ChemSpider	3400 ;
DrugBank	DB00536 ;
ECHA InfoCard	100.003.656
EC Number	204-021-8;
Gmelin Reference	100679
IUPHAR/BPS	4783;
MeSH	Guanidine
PubChem CID	3520;
UNII	JU58VJ6Y3B ;
CompTox Dashboard (EPA)	DTXSID0023117 ;
	InChI InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4) Key: ZRALSGWEFCBTJO-UHFFFAOYSA-N ;
	SMILES NC(N)=N;
Properties
Chemical formula	CH5N3
Molar mass	59.072 g·mol−1
Melting point	50 °C (122 °F; 323 K)
log P	−1.251
Basicity (pKb)	0.4
Conjugate acid	Guanidinium
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−57 – −55 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−1.0511 – −1.0531 MJ mol−1
Pharmacology
	Pharmacokinetics:
Biological half-life	7–8 hours
Hazards
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	475 mg/kg (oral, rat)
Related compounds
Related compounds	Urea; Biguanide;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

^ 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.
^ Cite error: The named reference Perrin was invoked but never defined (see the help page).
^ "Guanidine hydrochloride". ChemIDplus. National Library of Medicine. Archived from the original on 2014-08-12. Retrieved 2014-08-10.
^ 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.

[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.

[Perrin-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.

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