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CAS No. : | 1758-80-1 | MDL No. : | MFCD00082632 |
Formula : | C4H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OGNSCSPNOLGXSM-VKHMYHEASA-N |
M.W : | 118.13 | Pubchem ID : | 134490 |
Synonyms : |
L-2,4-Diaminobutyric acid
|
Chemical Name : | (S)-2,4-Diaminobutanoic acid |
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 28.53 |
TPSA : | 89.34 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -10.32 cm/s |
Log Po/w (iLOGP) : | 0.24 |
Log Po/w (XLOGP3) : | -4.64 |
Log Po/w (WLOGP) : | -1.25 |
Log Po/w (MLOGP) : | -3.46 |
Log Po/w (SILICOS-IT) : | -1.43 |
Consensus Log Po/w : | -2.11 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 3.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 2.55 |
Solubility : | 41800.0 mg/ml ; 354.0 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 3.39 |
Solubility : | 288000.0 mg/ml ; 2440.0 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 0.66 |
Solubility : | 537.0 mg/ml ; 4.55 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.48 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
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With water; palladium Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
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With sodium nitrite |
Yield | Reaction Conditions | Operation in experiment |
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With copper (II) carbonate hydroxide; water anschliessenden Behandeln mit Benzolsulfonylchlorid und wss.Natronlauge und Einleiten von Schwefelwasserstoff in eine Suspension des Reaktionsprodukts in Wasser; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper (II) carbonate hydroxide; water Behandeln der Reaktionsloesung mit Benzoylchlorid und wss. Natronlauge und Einleiten von Schwefelwasserstoff in eine Suspension des erhaltenen Kupfer(II)-Salzes in Wasser; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; sodium hydrogencarbonate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) CuCO3, (ii) /BRN= 515874/, AcOEt, NaHCO3; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium hydroxide In 1,4-dioxane; water at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In water; acetone at 45℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22 % Chromat. | In water for 40h; Irradiation; pH 2.0; |
Yield | Reaction Conditions | Operation in experiment |
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27.5% | With basic copper carbonate powder; sodium hydrogencarbonate In water for 12h; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride at 110℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
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31% | With basic copper carbonate powder; sodium hydrogencarbonate In water for 12h; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
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16% | In methanol |
Yield | Reaction Conditions | Operation in experiment |
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With lithium hydroxide In methanol; water at 40℃; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
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46% | With triethylamine In water; N,N-dimethyl-formamide at 57℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
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40% | With copper(II) carbonate; copper(II) hydroxide; sodium hydrogencarbonate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 30h; Heating / reflux; | 5 (S)-3-ammino-pyrrolidin-2-one Example 5 (S)-3-ammino-pyrrolidin-2-one 5M solution of hexamethyldisilazane (108 ml, 523 mmol) in CH3CN was added dropwise to a solution of (S)-2,4-diamino-butyric acid (10 g, 52.3 mmol) in CH3CN (150 ml) at room temperature. The resulting mixture was refluxed for 30 hours. The crude reaction was poured into cold MeOH (400 ml), stirred at room temperature for 30 minutes and then evaporated under vacuum. The resulting solid was dissolved in CH2Cl2 (700 ml) and the insoluble residue was removed by filtration under vacuum. The title compound was obtained (3.13 g) after evaporating the solution to dryness in a 60% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 3-[4-(2-(Z)-octadec-9-enyloxycarbonyl-ethylamino)-butylamino]-propionic acid (Z)-octadec-9-enyl ester dihydrochloride; L-2,4-diaminobutyrate With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h; Stage #2: With hydrogenchloride In ethyl acetate at 20℃; for 2h; | 6 The N-terminal-protected amino acid (0.41 mmol, 2.6 eq.), HCTU (168 mg, 0.41 mmol, 2.6 eq.), and diisopropylethylamine (0.19 mL, 1.10 mmol, 7.0 eq.) were added to a solution of the amine hydrochloride 6 (n = 4, R = oleyl; 150 mg, 0.156 mmol) in DMF-CH2Cl2 [1 : 1] (4.0 mL). The mixture was stirred at rt. under N2 for 18 h and then the mixture was concentrated to low volume and EtOAc EPO (30 mL) was added. The organic solution was washed successively with 5% aqueous KHSO4 solution (3 x 8 mL), 5% aqueous K2CO3 solution (3 x 8 mL) and brine (3 x 10 mL), then dried (Na2SO4) and concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting eluting with a solvent gradient of MeOH (50-100%) in water and then by silica gel column chromatography eluting with a solvent gradient of EtOAc (20-40%) in hexane. The residue was dissolved in EtOAc (2.0 mL) and 5.0N HCl in EtOAc (3.0 mL) was added. The resulting mixture was stirred at rt. for 2 h and then concentrated in vacuo and the solid residue triturated with diethyl ether (5.0 mL) to afford the surfactants 8a-d as white powders (75-93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 29.A Using the procedure described in the literature for the conversion of racemic 2,4-diaminobutyric acid into racemic 4-benzyloxycarbonylamino-2-tert-butoxycarbonylaminobutyric acid [A. D. Borthwick, S. J. Angier, A. J. Crame, A. M. Exall, T. M. Haley, G. J. Hart, A. M. Mason, A. M. K. Pennell and G. G. Weingarten, J. Med. Chem., 43(23), 4452-4464 (2000)], 2(S)-(-)-2,4-diaminobutyric acid (20.78 g, 108 mmoles) was converted into 4-benzyloxycarbonylamino-2(S)-(-)-tert-butoxycarbonylaminobutyric acid (17.07 g, 69%): FABMS: m/z 353.0 (MH+); δH (CDCl3) 1.43 (9H, s, COOC(CH3)3), 5.04/5.13 (2H, AB system, CH2C6H5) and 7.37 ppm (5H, m, CH2C6H5); δH (CDCl3) CH3: 28.4, 28.4, 28.4; CH2: 33.4, 37.2, 67.1; CH: 50.9, 128.2, 128.2, 128.6, 128.6, 128.6; C, 80.5, 136.4, 156.0, 157.1, 176.0; [α]D25° C.-13.5° (c=0.51, MeOH). The (S)-(-)-Isomer has also been prepared by an alternative procedure [K. Vogler, R. O. Studer, P. Lanz, W. Lergier and E. Bohni, Helv. Chim. Acta, 48(5), 1161-1177 (1965)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 62.6% 2: 21.1% | Stage #1: L-2,4-diaminobutyrate; acrylonitrile With sodium hydroxide In tetrahydrofuran; water at 20℃; for 51h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water Cooling; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cupriachelin With hydrogenchloride; water for 24h; Stage #2: With sodium hydrogencarbonate In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 37℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-carbamoyltransferase for 0.333333h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; In water; at 20℃; | S3: The reaction solution is cooled to room temperature.Adjust the pH to 5~6 with concentrated hydrochloric acid, remove the salt by cationic resin exchange resin,Elute with 5% ammonia water as eluent, concentrate the eluent, and adjust the pH to 2~3 with concentrated hydrochloric acid.Beating with ethanol to obtain crude L-2,4-diaminobutyrate,After drying the crude product, 394.2 g of a white solid was obtained.The yield was 85%. |
210 g | In water; for 24h;Reflux; | N2-tert-butoxycarbonyl-L-2,4-diaminobutyric acid 450 g, add 3 liters of deionized water and heat reflux for 24 hours, then concentrated to dryness, add anhydrous methanol crystals.Filtered, washed twice with methanol and dried at 60 C to give 210 g of free L-2,4-diaminobutyric acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.2 g | With palladium 10% on activated carbon; hydrogen; In methanol; for 24h; | 5.2 g of N 2 -benzyloxycarbonyl-L-2,4-diaminobutyric acid,Add 100 ml of anhydrous methanol,Add 0.5 g of 10% Pd / C, through hydrogen,Reaction for 24 hours,Then filter,Washed,The combined filtrates,Then concentrated to dryness,Add anhydrous methanol crystallization.filter,Washed twice with methanol,Dried at 60 C,2.2 g of free L-2,4-diaminobutyric acid was obtained,Melting point: 190-192 C, rotation = + 15 (c = 1 water). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
132 g | In methanol Reflux; | 10 Free L-2,4-diaminobutyric acid 200 g plus 2 liters of methanol, 600 g of trimethyl orthoacetate was heated to reflux for 12-36 hours, then concentrated anhydrous methanol was added.Filtered and rinsed with a small amount of methanol and dried at 60 ° C for 5 hours to obtain 132 g of (S) -2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid as a final product, which has an HPLC purity of 99.6% , Melting point: 280 ° C or more decomposition, optical rotation + 170 ° (C = 1MeOH), 1H-NMR (D)2O): 3.97-4.00 (1H, t), 3.18-3.40 (2H, m), 2.15 (3H, s), 2.02-2.10 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate In water at 40℃; | b.10 Preparation of Alpha and Gamma-DNP-L-2,4-Dab L-2,4-DAB (11.0 mg) and sodium carbonate (anhydrous, 20.0 mg) were dissolved in water (10 mL) at 40° C. FDNB (18.6 mg) was added, and the mixture was stirred vigorously by means of a magnetic stirrer at 40° C. The finely divided suspension of FDNB disappeared after about 30 min, indicating that the reaction was complete. Acidification of the resulting solution with concentrated HCl yielded mixture of α- and γ-DNP-L-2,4-DAB, which were further purified using HPLC C18 to yield pure α- and γ-DNP-L-2,4-DAB, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In hexane for 18h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 110℃; for 10h;Sealed tube; | To 1.0 mg of cichorinotoxin was added 1.0 mL of 6 N HCl, andthe mixture was frozen at -30 C and degassed under a highvacuum pump. The glass vessel was sealed and heated at110 C for 5 h, 10 h and 22 h to obtain the hydrolysates, each of which were concentrated to dryness. The residues were evaluatedusing an amino acid analyzer. Marfey?s method was employedto determine the stereochemistry of each of the aminoacids. The dried hydrolysates obtained by heating for 10 h weredissolved in 140 muL of H2O. To 25 muL of the solution wereadded 1% Marfey?s reagent ((1-fluoro-2,4-dinitro-5-fluorophenyl)-L-alaninamide, 1.8 muM) dissolved in acetone and 10 muLof 1 M NaHCO3 (10 muM). The solution was heated at 35 C for1 h, then 2 N aq HCl was added to quench the reaction, and thenit was concentrated to dryness. The residues were dissolved inDMSO and subjected to reversed-phase HPLC (C18) using amobile phase composed of 13% CH3CN/87% 50 mM triethylaminephosphate. Amino acid compositions of naturalcichorinotoxin (not Marfey?s derivatives) were analyzed byHitachi Keisoku Service Ltd (Tokyo) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With Rh/Al<SUB>2</SUB>O<SUB>3</SUB>; hydrogen; acetic acid In methanol at 20℃; for 2.5h; chemoselective reaction; | (2S)-2,4-diaminobutanoic acid (30) To a stirred solution of commercially available 29 (21.5 mg, 119.05 μmol) in MeOH (8.2 mL)acetic acid (102 μL, 1.79 mmol) and Rh/Al2O3 (12.3 mg, 5.95 μmol) were added. The suspension was stirred under H2 atmosphere (1 atm, balloon) at room temperature for 2.5 h.The mixture was filtered through 0.45 μm PTFE syringe filter, washed with MeOH and concentrated under reduced pressure to furnish 30 (12.1 mg, 86 % yield) as a white solid.NMR data are in agreement with those reported in the literature.[13]1H NMR (400 MHz, D2O, 25 °C): δ = 3.87 (t, J = 6.7 Hz, 1H, H2), 3.34 - 3.15 (m, 2H, H4a,H4b), 2.35 - 2.17 (m, 2H, H3a, H3b).13C NMR (101 MHz, D2O, 25 °C): δ = 173.2 (C1), 52.5 (C2), 36.5 (C4), 28.1 (C3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium hydroxide In 1,4-dioxane; water at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72 % | With triethylamine In methanol at 65℃; | 1.4; 2-6; 10 (4) Preparation of (S) -1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid After connecting a condenser to a 500mL two-neck round flask and circulating the refrigerant, 11.81g of (S)-2,4-diaminobutanoic acid, 10.2g of triethylamine, 120mL of methanol and 24.1g of trimethylorthoacetate prepared above was added and stirred under reflux at 65° C. for 12 hours to perform a cyclization reaction.Next, the completion of the reaction was confirmed by TLC, the reaction solution was cooled to room temperature (23-25 ° C), and then concentrated under reduced pressure to remove the solvent.50 mL of methanol and 110 mL of ethyl acetate were added to the residue, stirred at room temperature (20 to 25 ° C) for 2 hours, and then filtered to obtain 10.24 g of ectoin (72% yield) as the final target compound.In addition, the obtained ectoin was analyzed by liquid chromatography to confirm that the purity was 99.3%. |
[ 101854-78-8 ]
(R)-2,4-Diaminobutanoic acid hydrochloride
Similarity: 0.97
[ 89497-09-6 ]
(2S,4S)-2,4-Diaminopentanedioic acid
Similarity: 0.97
[ 73143-97-2 ]
(S)-2,4-Diaminobutanoic acid hydrobromide
Similarity: 0.97
Precautionary Statements-General | |
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H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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