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Guanidine hydrochloride(CAS No. 50-01-1)

Guanidine hydrochloride CH5N3.HCl (cas 50-01-1) Molecular Structure

50-01-1 Structure

Identification and Related Records

【Name】
Guanidine hydrochloride
【CAS Registry number】
50-01-1
【Synonyms】
Guanidine,monohydrochloride (8CI,9CI)
Buffer AL
Guanidine chloride
Guanidinehydrochloride
Guanidinium chloride
Guanidinium hydrochloride
【EINECS(EC#)】
200-002-3
【Molecular Formula】
CH5N3.HCl (Products with the same molecular formula)
【Molecular Weight】
95.53
【Inchi】
InChI=1/CH5N3.ClH/c2-1(3)4;/h(H5,2,3,4);1H
【InChIKey】
ZRALSGWEFCBTJO-UHFFFAOYSA-N
【Canonical SMILES】
C(=N)(N)N
【MOL File】
50-01-1.mol

Chemical and Physical Properties

【Appearance】
White cryst. powder
【Density】
1.34
【Melting Point】
179-186℃
【Boiling Point】
132.9 °C at 760 mmHg
【Refractive Index】
n20/D 1.465
【Flash Point】
34.2 °C
【Water】
2280 g/L (20℃)
【Solubilities】
2280 g/L (20 oC) in water
【Color/Form】
Deliquescent crystalline mass
【Stability】
Stable. Hygroscopic. Incompatible with strong oxidizing agents.
【HS Code】
29252000
【Storage temp】
Store at RT.
【Computed Properties】
Molecular Weight:59.0705 [g/mol]
Molecular Formula:CH5N3
XLogP3-AA:-1.3
H-Bond Donor:3
H-Bond Acceptor:1
Rotatable Bond Count:0
Exact Mass:59.048347
MonoIsotopic Mass:59.048347
Topological Polar Surface Area:75.9
Heavy Atom Count:4
Formal Charge:0
Complexity:26.3
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:3
Feature 3D Cation Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/38
【Safety Statements 】
S22
【Safety】

Safety Information of Guanidine hydrochloride (50-01-1):
Hazard Codes: Xn,Xi
Risk Statements: 22-36/38?
22:? Harmful if swallowed
36:? Irritating to the eyes???
38:? Irritating to the skin?
Safety Statements: 26-36-22
22:? Do not breathe dust
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:? Wear suitable protective clothing

【Sensitive】
Hygroscopic
【Formulations/Preparations】
Oral: Tablets 125 mg guanidine hydrochloride (Schering Canada for Key Pharm) /Guanidine hydrochloride/
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl guanidine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Guanidine Hydrochloride/
【Specification】

White cryst. powder
Safety Statements:26-36-22
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
22:Do not breathe dust
【Octanol/Water Partition Coefficient】
log Kow = -1.63 (est)
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

From ammonium thiocyanate or thiourea + ammonia
(1) By heating calcium cyanamide with ammonium iodide. (2) By treating urea with ammonia under pressure.
Free guanidine can be isolated from guanidine salts by reaction with a strong base such as an alkali metal hydroxide or methoxide. After removal of the precipitated salt the free guanidine base is obtained as colorless, waxy, very hygroscopic crystals.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.
【Therapeutic Uses】
Guanidine is indicated 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. The Eaton-Lambert syndrome is ordinarily differentiated from myasthenia gravis by the usual association of the syndrome with small cell carcinoma of the lung, but myography may be necessary to make the diagnosis. /Guanidine hydrochloride/
... Low-dose guanidine and pyridostigmine combination therapy /was used/ in 9 patients with LEMS /Lambert-Eaton myasthenic syndrome/ and ... its long-term safety and effectiveness /was analyzed/. In all patients, a liberal amount of pyridostigmine was used, while daily guanidine dose was kept below 1000 mg a day, and guanidine was given between pyridostigmine dosings. This combination therapy was used for 3 to 102 months (mean: 34.1 months) and improved clinical status in all patients. Although guanidine had to be discontinued due to severe gastrointestinal symptoms in 3 cases, no serious side reactions such as bone marrow suppressions or signs of renal insufficiency developed in any case ... /Guanidine hydrochloride/ [Oh SJ et al; Muscle Nerve 20(9):1146-52 (1997)]
【Biomedical Effects and Toxicity】
Accumulation of specific guanidine compounds (GCs) has been related to neurological, cardiovascular, hematological, and immunological complications of renal failure ... The obvious increases of urea, guanidinosuccinic acid, creatinine, guanidine, methylguanidine, and N(G)N(G)-dimethylarginine (symmetrical dimethylarginine) seen in blood of oldest heterozygous and younger homozygous polycystic kidney disease (PKD) rats were largely within the same range as those found in the studied human PKD population, especially in patients with a glomerular filtration rate below 60 mL/min/1.73 sq m. The decreased levels of plasma guanidinoacetic acid seen at end-stage renal disease in homozygous and oldest heterozygous PKD/Mhm rats were also observed in serum of patients with a glomerular filtration rate below 20 mL/min/1.73 sq m ... /Guanidino compounds/ [Torremans A et al; Kidney Int 69(11):2003-12 (2006)] PubMed Abstract
Brush-border membrane vesicles were prepared from donor human kidneys ... Uptake of (14)C-guanidine ... in the vesicles, as determined by rapid filtration, was significantly greater in the presence of an outwardly-directed proton gradient, at all early time points, than in the absence of the gradient ... Evidence was obtained suggesting that the transporter for guanidine is distinct from the previously described organic cation proton antiporter for TEA. /Tetraethylammonium/ [Chun JK et al; Pharmaceutical Research 14(7): 936-941 (1997)] PubMed Abstract
The characteristics of guanidine uptake in brush-border membrane vesicles isolated from rabbit renal cortex were investigated. Guanidine uptake was markedly stimulated by an outwardly directed H+ gradient, resulting in a transient uphill transport. This stimulation was not due to an inside-negative, H+-diffusion potential because an ionophore-induced H+-diffusion potential and a K+-diffusion potential (both inside-negative) failed to enhance guanidine uptake. The H+ gradient itself appeared to be the driving force for the uptake ... [Miyamoto Y et al; Am J Physiol 256(4 Pt 2):F540-8 (1989)] PubMed Abstract
... The plasma, erythrocyte, and urinary concentration of guanidino compounds in 30 hemodialysis patients and 15 patients with chronic renal failure who had not undergone hemodialysis /were determined/ ... Plasma levels of taurocyamine, guanidinosuccinic acid, alpha-N-acetyl-L-arginine, creatine, guanidinobutyric acid, guanidine, and methylguanidine were significantly increased in patients with chronic renal failure with or without hemodialysis. In contrast, plasma guanidinoacetic acid concentrations were significantly decreased. Erythrocyte concentrations of creatinine, guanidinosuccinic acid, guanidine and methylguanidine were also markedly elevated. No correlation was observed between plasma creatinine concentration and erythrocyte concentration of guanidinosuccinic acid or methylguanidine. However, there was a significant correlation between plasma and erythrocyte methylguanidine, and between plasma and erythrocyte guanidinosuccinic acid. /Guanidino compounds/ [Tanaka A et al; Ren Fail 21(5):499-514 (1999)] PubMed Abstract
Twelve guanidino compounds were determined in simultaneously sampled serum and cerebrospinal fluid of eight non-dialyzed patients with renal insufficiency ... In patients with serum urea levels about 10 times higher than in controls, the levels of guanidinosuccinic acid, creatinine, guanidine and methylguanidine, in serum as well as in cerebrospinal fluid, are at least 10 times higher than in control subjects. The levels of argininic acid and N-alpha-acetylarginine (in serum) and gamma-guanidinobutyric acid (in cerebrospinal fluid) are slightly increased (less than 10 X). The levels of the other guanidino compounds are close to normal values. A significant positive correlation exists between the guanidinosuccinic acid, creatinine and guanidine levels in serum and cerebrospinal fluid ... /Guanidino compounds/ [De Deyn PP et al; Clin Chim Acta 167(1):81-8 (1987)] PubMed Abstract
Guanidine ... compound levels in 28 brain regions in control and uremic brains /was reported/. In all brain regions studied, in controls as well as in uremic patients, concentrations of alpha-keto-delta-guanidinovaleric acid, alpha-N-acetylarginine and beta-guanidinopropionic acid remained below detection limits. Creatine, guanidinoacetic acid, argininic acid, gamma-guanidinobutyric acid, arginine and homoarginine were not increased in uremic patients. Argininic acid and homoarginine were detectable in some brain regions only. Creatine concentrations varied from 2500 + or - 2100 nmol/g tissue in hypophysis to 10500 + or - 1200 nmol/g tissue in cerebellar cortex. Even more pronounced regional differences were found for gamma-guanidinobutyric acid with the lowest concentration in the caudate nucleus (0.6 + or - 0.3 nmol/g tissue) and highest in substantia nigra, pallidum and cerebellar dentate nucleus (8.3 + or - 2.8 nmol/g tissue). The guanidinosuccinic acid levels were below detection limit in controls in the majority of brain regions. Taking into account the detection limit of guanidinosuccinic acid for a certain amount of tissue applied to the analytical system, important increases (approx up to > 100 fold) were observed in all brain regions of uremic patients. Accumulation of guanidinosuccinic acid increased with increasing degree of renal failure with levels up to 65 nmol/g tissue in the hypophysis. Creatinine concentrations were also found to be increased in uremic brain regions but increases seemed to be less strictly related to serum urea levels. Guanidine and methylguanidine were found only occasionally in brain regions of controls while respectively 100- and 30-fold increases were found in brain regions of uremic subjects. Levels of guanidinosuccinic acid and creatinine in uremic brain were comparable to those previously observed in brain of experimental animals displaying convulsions following intraperitoneal injection of the respective compounds ... /Guanidino compounds/ [De Deyn PP et al; Neurochem Int 27(3):227-37 (1995)] PubMed Abstract
... The concentrations of 13 guanidine compounds in serum were measured in 29 patients with chronic renal failure treated by chronic intermittent hemodialysis ... Substantial increases in guanidinosuccinic acid, creatine, N-alpha-acetylarginine, creatinine, guanidine and methylguanidine were found. The values obtained for taurocyamine and beta-guanidinoproprionic acid were much lower than those reported by others: a much smaller increase was observed for beta-guanidinoproprionic acid and taurocyamine was only doubled in 4 of 29 uraemic patients. The concentrations of other guanidino compounds such as arginine and guanidinoacetic acid were normal. No differences were found between the polycystic renal disease, the chronic glomerulonephritis and the interstitial nephritis subgroups. /Guanidino compounds/ [De Deyn P et al; Clin Chim Acta 157(2):143-50 (1986)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that guanidine is expected to have very high mobility in soil(SRC). However, guanidine has a pKa of 12.5(3) and should exist almost entirely as a cation under environmental conditions (pH 5-9)(SRC). As a result, guanidine may have greater adsorption and less mobility than its estimated Koc value indicates since cations generally adsorb more strongly to soils containing organic carbon and clay than neutral species(4). Volatilization from moist soil surfaces is not an important environmental fate process since cations do not volatilize(SRC). The potential to volatilize from dry soil surfaces exists based upon an estimated vapor pressure of 2.2 mm Hg(SRC), determined from a fragment constant method(5). Guanidine was degraded in soil samples incubated under aerobic conditions at varying rates as a function of the initial starting concentration(6). At an initial concentration of 10 mg/kg, guanidine was 78% biodegraded after 10 days; however, at an initial concentration of 400 mg/kg, guanidine was 62% biodegraded after 25 days(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that guanidine is not expected to adsorb to suspended solids and sediment(SRC). However, guanidine has a pKa of 12.5(3) and should exist almost entirely as a cation under environmental conditions (pH 5-9)(SRC). As a result, guanidine may have greater adsorption to suspended solids and sediment than its estimated Koc value indicates(SRC). Volatilization of guanidine from water surfaces will not be an important fate process, since cations do not volatilize(SRC). According to a classification scheme(4), BCF values in the range of
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), guanidine, which has an estimated vapor pressure of 2.2 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase guanidine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 9 hours(SRC), calculated from its rate constant of 4.2X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Guanidine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

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