ContaminantDB: Guanidine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:49:15 UTC

Update Date

2026-04-16 22:17:00 UTC

Accession Number

CHEM003132

Identification

Common Name

Guanidine

Class

Small Molecule

Description

Guaniidine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH. With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed). Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amide
Amine
Drug
Food Toxin
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Aminomethanamidine	ChEBI
Gu	ChEBI
Guanidin	ChEBI
H2N-C(=nh)-NH2	ChEBI
Iminourea	ChEBI
Carbamidine	Kegg
(4-Aminobutyl) guanidine	HMDB
Aminoformamidine	HMDB
Carbamamidine	HMDB
Imidourea	HMDB
Guanidine hydrochloride	HMDB
Guanidine monohydrate	HMDB
Guanidine monohydrochloride	HMDB
Guanidine sulfate	HMDB
Guanidium chloride	HMDB
Chloride, guanidinium	HMDB
Guanidine monohydroiodine	HMDB
Guanidine sulfate (1:1)	HMDB
Guanidine sulfate (2:1)	HMDB
Guanidine sulfite (1:1)	HMDB
Guanidinium	HMDB
Hydrochloride, guanidine	HMDB
Monohydrobromide, guanidine	HMDB
Monohydrochloride, guanidine	HMDB
Phosphate, guanidine	HMDB
Guanidine monohydrobromide	HMDB
Guanidine phosphate	HMDB
Monohydroiodine, guanidine	HMDB
Nitrate, guanidine	HMDB
Chloride, guanidium	HMDB
Guanidine nitrate	HMDB
Guanidinium chloride	HMDB
Monohydrate, guanidine	HMDB
Sulfate, guanidine	HMDB

Chemical Formula

CH₅N₃

Average Molecular Mass

59.071 g/mol

Monoisotopic Mass

59.048 g/mol

CAS Registry Number

113-00-8

IUPAC Name

guanidine

Traditional Name

guanidine

SMILES

NC(N)=N

InChI Identifier

InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)

InChI Key

ZRALSGWEFCBTJO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Guanidines

Direct Parent

Guanidines

Alternative Parents

Substituents

Guanidine
Carboximidamide
Organopnictogen compound
Hydrocarbon derivative
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:42820 )
guanidines (CHEBI:42820 )
carboxamidine (CHEBI:42820 )
a small molecule (CPD-13517 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Brain
Cartilage
Fibroblasts
Intestine
Kidney
Liver
Muscle
Nerve Cells
Pancreas
Placenta
Platelet
Spleen
Testes

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	50°C
Boiling Point	Not Available
Solubility	1840 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.2	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Basic)	12.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	25.86 m³·mol⁻¹	ChemAxon
Polarizability	5.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00dj-0920000000-b2c19a9125b059b573fd	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00dj-0920000000-b2c19a9125b059b573fd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9000000000-6e00e9be1957670e422b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9000000000-4df2949d18a754b6aa19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-18b92fabd8878a75412f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-6675e99565dbe0735311	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-0bf566c21de369198214	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9000000000-b4670d41c5cfae856086	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-9431377731da436c5aa7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9000000000-2280b2044ac4a1f8b7fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-8278836749ed05b02fb3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-154d1302bda42480ad7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-ab782a456c989f06bfc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-36e3aa30c6cc4afb2049	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-1c8520c5f7efb1187e43	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed and distributed

Mechanism of Toxicity

Uremic toxins such as guaniidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (3). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (4).

Metabolism

Not metabolized. Half Life: 7-8 hours

Toxicity Values

LD₅₀ = 475 mg/kg (oral, rat).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of Eaton-Lambert. It is not indicated for treating myasthenia gravis.

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

DB00536

HMDB ID

HMDB0001842

FooDB ID

FDB005416

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6342

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Helmut Hoffmann, Carlhans Suling, “Process for the production of guanidine salts of aliphatic mercaptosulphonic acids.” U.S. Patent US3956368, issued November, 1954.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=8070089

2. De Deyn PP, Marescau B, D'Hooge R, Possemiers I, Nagler J, Mahler C: Guanidino compound levels in brain regions of non-dialyzed uremic patients. Neurochem Int. 1995 Sep;27(3):227-37.

3. Bullough A, Karadia S, Watters M: Phaeochromocytoma: an unusual cause of hypertension in pregnancy. Anaesthesia. 2001 Jan;56(1):43-6.

4. Mannik M, Person RE: Deep penetration of antibodies into the articular cartilage of patients with rheumatoid arthritis. Rheumatol Int. 1994;14(3):95-102.

5. Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10.

6. Eropkin MIu, Smirnova TD, Eropkina EM, Mamaeva EG: [The study of the Ca2+ role in cytotoxic response of human cells in culture to the action of xenobiotics]. Tsitologiia. 2000;42(2):154-9.

7. Rufanova VA, Sorokin A: CrkII associates with BCAR3 in response to endothelin-1 in human glomerular mesangial cells. Exp Biol Med (Maywood). 2006 Jun;231(6):752-6.

8. Bjornsson S: Size-dependent separation of proteoglycans by electrophoresis in gels of pure agarose. Anal Biochem. 1993 May 1;210(2):292-8.

9. Sakamoto N, Toge T, Nishiyama M: Tumor-specific synergistic therapy of mitomycin C: modulation of bioreductive activation. Hiroshima J Med Sci. 1997 Jun;46(2):67-73.