Not to be confused with Guanine, Guanosine, or Guanfacine.
Guanidine
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| Names |
| IUPAC names
Guanidine[1]
Iminomethanediamine
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| Identifiers |
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CAS Number
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113-00-8 Y |
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Beilstein Reference
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506044 |
| ChEBI |
CHEBI:42820 Y |
| ChEMBL |
ChEMBL821 Y |
| ChemSpider |
3400 Y |
| DrugBank |
DB00536 Y |
| EC Number |
204-021-8 |
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Gmelin Reference
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100679 |
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IUPHAR/BPS
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4783 |
| Jmol interactive 3D |
Image
Image |
| MeSH |
Guanidine |
| PubChem |
3520 |
| UNII |
JU58VJ6Y3B Y |
InChI
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InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4) Y
Key: ZRALSGWEFCBTJO-UHFFFAOYSA-N Y
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SMILES
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[nH]:c(:[nH2]):[nH2]
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NC(N)=N
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| Properties |
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Chemical formula
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CH5N3 |
| Molar mass |
59.07 g·mol−1 |
| Melting point |
50 °C (122 °F; 323 K) |
| log P |
−1.251 |
| Thermochemistry |
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Std enthalpy of
formation (ΔfHo298)
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−57–−55 kJ mol−1 |
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Std enthalpy of
combustion (ΔcHo298)
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−1.0511–−1.0531 MJ mol−1 |
| Pharmacology |
| Pharmacokinetics: |
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Biological half-life
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7–8 hours |
| Hazards |
| Lethal dose or concentration (LD, LC): |
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LD50 (Median dose)
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475 mg/kg (oral, rat)[2] |
| Related compounds |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is YN ?) |
| Infobox references |
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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 as a normal product of protein metabolism. Guanidine is the functional group on the side chain of arginine.
Contents
- 1 Structure
- 2 Production
- 3 Guanidinium salts
- 3.1 Industry
- 3.2 Biochemistry
- 3.3 Other
- 4 Guanidine derivatives
- 5 See also
- 6 References
Structure
Guanidine can be thought of as a nitrogenous analogue of the carbonic acid functional group. That is, the C=O group in carbonic acid is replaced by a C=NH group, and each OH is replaced by a NH2 group.[3] A detailed crystallographic analysis of guanidine was elucidated 148 years after its first synthesis, despite the simplicity of the molecule.[4] In the year 2013, the positions of the hydrogen atoms and their displacement parameters were accurately determined using single-crystal neutron diffraction.[5]
Production
Guanidine can be obtained from natural sources, being first isolated by Adolph Strecker via the degradation of guanine.[6]
The compound was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano.[7] The commercial route involves a two step process starting with the reaction of dicyandiamide with ammonium salts. Via the intermediacy of biguanidine, this ammonolysis step affords salts of the guanidinium cation (see below). In the second step, the salt is treated with base, such as sodium methoxide.[6]
Guanidinium salts
With a pKa of 13.7, guanidine is a moderately strong base. In neutral water, it exists exclusively as guanidinium [C(NH2)3]+). Most guanidine derivatives are in fact such salts.
Industry
The main salt of commercial interest is the nitrate [C(NH2)3]NO3. It is used as a propellant, for example in air bags.
Biochemistry
Guanidine is protonated in physiological conditions. This conjugate acid is called the guanidinium cation, [CH6N3]+. It is a highly stable +1 cation in aqueous solution due to the efficient resonance stabilization of the charge and efficient solvation by water molecules. As a result, its pKa is 13.6[8] meaning that guanidine is a very strong base in water.
Guanidinium chloride has chaotropic properties and is used to denature proteins. Guanidine hydrochloride is known to denature proteins with a linear relationship between concentration and free energy of unfolding. In aqueous solutions containing 6 M guanidinium chloride, almost all proteins lose their entire secondary structure and become randomly coiled peptide chains. Guanidinium thiocyanate is also used for its denaturing effect on various biological samples. Guanidine hydrochloride[9] is used as an adjuvant in treatment of botulism, introduced in 1968,[10] but now its role is considered controversial[11] - because in some patients there was no improvement after this drug administration.
Other
Guanidinium hydroxide is the active ingredient in some non-lye hair relaxers.
Guanidine derivatives
The general structure of a guanidine
Guanidines are a group of organic compounds sharing a common functional group with the general structure (R1R2N)(R3R4N)C=N-R5. The central bond within this group is that of an imine, and the group is related structurally to amidines and ureas. Examples of guanidines are arginine, triazabicyclodecene, saxitoxin, and creatine.
See also
- Category:Guanidines
- Sakaguchi test
References
- ^ "Guanidine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 29 February 2012.
- ^ http://chem.sis.nlm.nih.gov/chemidplus/rn/50-01-1
- ^ M. Goebel, T.M. Klapoetke (2007). "First structural characterization of guanidine". Chem. Commun. 43 (30): 3180–2. doi:10.1039/B705100J.
- ^ T. Yamada, X. Liu, U. Englert, H. Yamane, R. Dronskowski (2009). "Solid-state structure of free base guanidine achieved at last". Chem. Eur. J. 15 (23): 5651–5. doi:10.1002/chem.200900508. PMID 19388036.
- ^ P. K. Sawinski, M. Meven, U. Englert, R. Dronskowski (2013). "Single-Crystal Neutron Diffraction Study on Guanidine, CN3H5". Cryst. Growth Des. 13: 1730–5. doi:10.1021/cg400054k.
- ^ a b Thomas Güthner, Bernd Mertschenk and Bernd Schulz "Guanidine and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_545.pub2
- ^ Strecker, A (1861). "Untersuchungen über die chemischen Beziehungen zwischen Guanin, Xanthin, Theobromin, Caffeïn und Kreatinin". Liebigs Ann. Chem. 118 (2): 151–177. doi:10.1002/jlac.18611180203.
- ^ Perrin, D.D., Dissociation Constants of Organic Bases in Aqueous Solution, Butterworths, London, 1965; Supplement, 1972.
- ^ Kaplan, J. E.; Davis, L. E.; Narayan, V; Koster, J; Katzenstein, D (1979). "Botulism, type A, and treatment with guanidine". Annals of Neurology 6 (1): 69–71. doi:10.1002/ana.410060117. PMID 389150.
- ^ http://jama.ama-assn.org/content/240/21/2276.abstract
- ^ Pediatric anaerobic infections: diagnosis and management, p.529
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Antidiarrheals, intestinal anti-inflammatory and anti-infective agents (A07)
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| Rehydration |
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| Intestinal anti-infectives |
- Antibiotics
- Amphotericin B
- Colistin
- Fidaxomicin
- Kanamycin
- Natamycin
- Neomycin
- Nystatin
- Paromomycin
- Polymyxin B
- Rifaximin
- Streptomycin
- Vancomycin
- Sulfonamides
- Phthalylsulfathiazole
- Succinylsulfathiazole
- Sulfaguanidine
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| Intestinal adsorbents |
- Charcoal
- Bismuth
- Pectin
- Kaolin
- Crospovidone
- Attapulgite
- Diosmectite
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| Antipropulsives (opioids) |
- Opium tincture (laudanum)
- Codeine
- Morphine
- Camphorated opium tincture (paregoric)
- crosses BBB: Diphenoxylate (Diphenoxylate/atropine)
- Difenoxin
- does not cross BBB: Eluxadoline
- Loperamide
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| Intestinal anti-inflammatory agents |
- corticosteroids acting locally
- Prednisolone
- Hydrocortisone
- Prednisone
- Betamethasone
- Tixocortol
- Budesonide
- Beclometasone
- antiallergic agents, excluding corticosteroids
- aminosalicylic acid and similar agents
- Sulfasalazine
- Mesalazine
- Olsalazine
- Balsalazide
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| Antidiarrheal micro-organisms |
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| Other antidiarrheals |
- Albumin tannate
- Ceratonia
- Crofelemer
- Octreotide
- Racecadotril
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Index of digestion
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| Description |
- Anatomy
- Physiology
- Development
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| Disease |
- Congenital
- Neoplasms and cancer
- Inflammatory bowel disease
- Gluten sensitivity
- Other
- Symptoms and signs
- Blood tests
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| Treatment |
- Procedures
- Drugs
- anabolic steroids
- antacids
- diarrhoea and infection
- bile and liver
- functional gastrointestinal disorders
- laxatives
- peptic ulcer and reflux
- nausea and vomiting
- other
- Surgery
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Sympatholytic (and closely related) antihypertensives (C02)
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Sympatholytics
(antagonize α-adrenergic
vasoconstriction) |
| Central |
| α2 agonist |
- Clonidine
- Guanabenz
- Guanfacine
- Methyldopa#
- Tiamenidine‡
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| Adrenergic release inhibitors |
- Bethanidine
- Bretylium
- Debrisoquine
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoclor
- Guanazodine
- Guanoxabenz
- Guanoxan
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| Imidazoline receptor agonist |
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| Ganglion-blocking/nicotinic antagonist |
- Hexamethonium‡
- Mecamylamine
- Pentolinium
- Trimethaphan
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| Peripheral |
| Indirect |
| MAOI |
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| Adrenergic uptake inhibitor |
- Bietaserpine
- Deserpidine
- Methoserpidine
- Rescinnamine
- Reserpine
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| Tyrosine hydroxylase inhibitor |
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| Direct |
| α1 blockers |
- Prazosin
- Indoramin
- Trimazosin
- Doxazosin
- Urapidil
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| Non-selective α blocker |
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| Other antagonists |
| Serotonin antagonist |
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| Endothelin antagonist (for PH) |
- dual (Bosentan, Macitentan)
- selective (Ambrisentan, Sitaxentan)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of the circulatory system
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| Description |
- Anatomy
- Arteries
- head and neck
- arms
- chest
- abdomen
- legs
- Veins
- head and neck
- arms
- chest
- abdomen and pelvis
- legs
- Development
- Cells
- Physiology
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| Disease |
- Congenital
- Neoplasms and cancer
- Lymphatic vessels
- Injury
- Vasculitis
- Other
- Symptoms and signs
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| Treatment |
- Procedures
- Drugs
- beta blockers
- channel blockers
- diuretics
- nonsympatholytic vasodilatory antihypertensives
- peripheral vasodilators
- renin–angiotensin system
- sympatholytic antihypertensives
- vasoprotectives
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| Authority control |
- LCCN: sh85057589
- GND: 4158491-0
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