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{{Chembox|verifiedrevid=450914731|ImageFile1=Guanidinium chloride V.2.svg|ImageSize1=120px|ImageFileL2=Guanidinium-ion-3D-balls.png|ImageFileR2=Chloride-ion-3D-vdW.png|IUPACName=Carbamimidoylazanium chloride|OtherNames=Guanidine hydrochloride|Section1={{Chembox Identifiers |
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{{Chembox |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| verifiedrevid = 443851585 |
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| ImageFile = Guanidinium chloride V.2.svg |
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| ImageSize = 120px |
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| IUPACName = Carbamimidoylazanium chloride |
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| OtherNames = Guanidine hydrochloride |
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| Section1 = {{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 3YQC9ZY4YB |
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| UNII = 3YQC9ZY4YB |
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| KEGG = D11626 |
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| InChIKey = PJJJBBJSCAKJQF-UHFFFAOYAG |
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| InChIKey = PJJJBBJSCAKJQF-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 50-01-1 |
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| CASNo = 50-01-1 |
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| PubChem = 10855382 |
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| PubChem = 10855382 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5540 |
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| ChemSpiderID = 5540 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 32735 |
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| ChEBI = 32735 |
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| SMILES = Cl.=C(N)N |
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| SMILES = Cl.=C(N)N |
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| InChI = 1/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H |
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| InChI = 1/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H |
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}}|Section2={{Chembox Properties |
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| C=1 | H=6 | Cl=1 | N=3 |
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| Section2 = {{Chembox Properties |
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| Appearance = ] crystals |
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| C=1 | H=6 | Cl=1 | N=3 |
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| Density = 1.354 g/cm<sup>3</sup> at 20 °C |
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| Appearance = ] crystals |
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| MeltingPtC = 182.3 |
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| Density = 1.354 g/cm<sup>3</sup> at 20 °C |
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| MeltingPtC = 182.3 |
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| BoilingPt = |
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| BoilingPt = |
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| pKa = 13.6 |
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| Solubility = 2.15 g/ml at 20 °C <ref>{{Cite web|url=http://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=0894|title = Icsc 0894 - Guanidine Hydrochloride}}</ref> |
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| Solubility = very soluble in water and ]<ref name="hand"> |
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}}|Section3={{Chembox Hazards |
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{{Cite book |
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| ExternalSDS = |
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| last = Lide |
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| first = David R. |
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| FlashPt = |
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| AutoignitionPt = |
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| author-link = |
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| first2 = |
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| date = |
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| year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| edition = 87 |
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| volume = |
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| series = |
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| publication-place = Boca Raton, FL |
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| place = |
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| publisher = CRC Press |
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| id = |
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| isbn = 0849305942 |
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| doi = |
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| pages = 3–296 |
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| url = |
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}}</ref> |
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}} |
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| Section3 = {{Chembox Hazards |
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| ExternalMSDS = |
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| FlashPt = |
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'''Guanidinium chloride''' or '''guanidine hydrochloride''', usually abbreviated GdmCl and sometimes GndCl or GuHCl, is the ] salt of ]. |
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'''Guanidinium chloride''' or '''guanidine hydrochloride''', usually abbreviated GdmCl and sometimes GdnHCl or GuHCl, is the ] salt of ]. |
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== Structure == |
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==Use in protein denaturation== |
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Guanidinium chloride crystallizes in ] ] ''Pbca''. The ] consists of a network of ] ]s and ] ] linked by N–H···Cl ]s.<ref name=":0" /> |
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== Acidity == |
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Guanidinium chloride is one of the strongest ]s used in physiochemical studies of ]. In 6 molar guanidinium chloride solution, all ]s with well ordered structure lose it, and most of them become randomly coiled, i.e. they do not contain any residual structure. However, at concentrations in the millimolar range in vivo, proteins are shown to change conformation from the ] to non-prion state. This change requires a switch from a ] based structure to a ] based structure.{{Citation needed|date=June 2010}} |
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Guanidinium chloride is a weak acid with a pK<sub>a</sub> of 13.6. The reason that it is such a weak acid is the complete delocalisation of the positive charge through 3 nitrogen atoms (plus a little bit positive charge on carbon). However, some stronger bases can deprotonate it, such as ]: |
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<chem>C(NH2)3+ + OH- <=>> HNC(NH2)2 + H2O</chem> |
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== Historical survey == |
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Petrunkin and Petrunkin (1927, 1928) appear to be the first who studied the binding of GndCl to ] and a mixture of thermally denatured protein from brain extract. Greenstein (1938, 1939), however, appears to be the first to discover the high denaturing action of guanidinium ]s and thiocyanates in following the liberation of ] groups in ] and few other proteins as a function of salt concentration.<ref>{{cite book|last=Lapange|first=Savo|title=Physicochemical aspects of protein denaturation|location=New York|publisher=Wiley|year=1978|isbn=0471034096}}</ref> |
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The equilibrium is not complete because the acidity difference between guanidinium and water is not large (The approximate pK<sub>a</sub> values: 13.6 vs 15.7). |
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== Medical Uses == |
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Complete ] should be done with extremely strong bases, such as ]. |
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Guanidine hydrochloride is indicated for the reduction of the symptoms of muscle weakness and easy fatigability associated with ]. It is not indicated for treating myasthenia gravis. It apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes. Initial dosage is usually between 10 and 15 mg/kg (5 to 7 mg/pound) of body weight per day in 3 or 4 divided doses. This dosage may be gradually increased to a total daily dosage of 35 mg/kg (16 mg/pound) of body weight per day or up to the development of side effects. Side effects include increased peristalsis and diarrhea. Fatal bone-marrow suppression, apparently dose related, can occur with guanidine. |
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<chem>C(NH2)3+Cl- + Li+N(C3H7)2- -> HNC(NH2)2 + HN(C3H7)2 + LiCl</chem> |
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== Use in protein denaturation == |
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Guanidinium chloride is a strong ] and one of the strongest ]s used in physiochemical studies of ]. It also has the ability to decrease enzyme activity and increase the solubility of hydrophobic molecules.<ref name=":0">{{Cite web|url=https://biospectra.us/bp/products/biological-buffers/all-biological-buffers/guanidine-hydrochloride-detail.html|title=BioSpectra - Guanidine Hydrochloride|website=biospectra.us|access-date=2017-06-08}}</ref> At high concentrations of guanidinium chloride (e.g., 6 ]), ]s lose their ordered ], and they tend to become ], i.e. they do not contain any residual structure. However, at concentrations in the millimolar range in vivo, guanidinium chloride has been shown to "cure" ] positive yeast cells (i.e. cells exhibiting a prion positive phenotype revert to a prion negative phenotype). This is the result of inhibition of the ] chaperone protein known to play an important role in prion fiber fragmentation and propagation.<ref>Ferreira PC, Ness F, Edwards SR, Cox BS, Tuite MF (2001) The elimination of the yeast prion by guanidine hydrochloride is the result of Hsp104 inactivation. Mol Microbiol 40 (6):1357-1369.</ref><ref>Ness F, Ferreira P, Cox BS, Tuite MF (2002) Guanidine hydrochloride inhibits the generation of prion "seeds" but not prion protein aggregation in yeast. Mol Cell Biol 22 (15):5593-5605.</ref><ref>Eaglestone SS, Ruddock LW, Cox BS, Tuite MF (2000) Guanidine hydrochloride blocks a critical step in the propagation of the prion-like determinant of Saccharomyces cerevisiae. Proc Natl Acad Sci USA 97 (1):240-244.</ref> |
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== Historical survey == |
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Petrunkin and Petrunkin (1927, 1928) appear to be the first who studied the binding of GnHCl to ] and a mixture of thermally denatured protein from brain extract. Greenstein (1938, 1939), however, appears to be the first to discover the high denaturing action of guanidinium ]s and thiocyanates in following the liberation of ] groups in ] and other proteins as a function of salt concentration.<ref>{{cite book|last=Lapange|first=Savo|title=Physicochemical aspects of protein denaturation|location=New York|publisher=Wiley|year=1978|isbn=0-471-03409-6}}</ref> |
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== Medical uses == |
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Guanidine hydrochloride is indicated for the reduction of the symptoms of muscle weakness and easy fatigability associated with ]. It is not indicated for treating myasthenia gravis. It apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes. Initial dosage is usually between 10 and 15 mg/kg (5 to 7 mg/pound) of body weight per day in 3 or 4 divided doses. This dosage may be gradually increased to a total daily dosage of 35 mg/kg (16 mg/pound) of body weight per day or up to the development of side effects. Side effects may include increased peristalsis, diarrhea, paresthesia (tingling and numbness), and nausea. Fatal bone-marrow suppression, apparently dose related, can occur with guanidine.<ref name="Wiederholt">{{cite journal |last1=Wiederholt |first1=W. C. |title=Guanidine hydrochloride therapy in neuromuscular disorders |journal=Western Journal of Medicine |date=1975 |volume=123 |issue=2 |pages=132–133|pmid=1179724 }}</ref> |
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== References == |
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