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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/04 00:47:42」(JST)

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Tris or Tris(hydroxymethyl)aminomethane or THAM is an organic compound with the formula (HOCH₂)₃CNH₂. Tris is extensively used in biochemistry and molecular biology.^[1] In biochemistry, Tris is widely used as a component of buffer solutions, such as in TAE and TBE buffer, especially for solutions of nucleic acids. It contains a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes.

Buffering features

Tris has a pK_a of 8.07 at 25 °C, which implies that the buffer has an effective pH range between 7.5 and 9.0.

Buffer details

The pK_a declines approximately 0.03 units per degree Celsius rise in temperature.^[2]^[3]
Silver-containing single-junction pH electrodes (e.g., silver chloride electrode) are incompatible with Tris (Ag-tris precipitation clogs the junction). Double-junction electrodes are resistant to this problem, and non-silver containing electrodes are immune.
Making buffer solutions by neutralizing TrisHCl requires attention to the attendant changes in ionic strength.

Buffer inhibition

Tris inhibits a number of enzymes,^[4]^[5] and therefore it should be used with care when studying proteins.

Preparation

Tris is prepared industrially in two steps from nitromethane via the intermediate (HOCH₂)₃CNO₂. Reduction of the latter gives tris(hydroxymethyl)aminomethane.^[6]

Uses

The useful buffer range for tris (7-9) coincides with the physiological pH typical of most living organisms. This, and its low cost, make tris one of the most common buffers in the biology/biochemistry laboratory. Tris is also used as a primary standard to standardize acid solutions for chemical analysis.

Tris is used to increase membrane permeability of cell membranes.^[7]

Medical

Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis.^[8]^[9]

References

^ Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
^ El-Harakany, A.A.; Abdel Halima, F.M. and Barakat, A.O. (1984). "Dissociation constants and related thermodynamic quantities of the protonated acid form of tris-(hydroxymethyl)-aminomethane in mixtures of 2-methoxyethanol and water at different temperatures". J. Electroanal. Chem. 162 (1–2): 285–305. doi:10.1016/S0022-0728(84)80171-0.
^ Vega, C.A.; Butler, R.A. et al. (1985). "Thermodynamics of the Dissociation of Protonated Tris(hydroxymethy1)aminomethane in 25 and 50 wt % 2-Propanol from 5 to 45 °C". J. Chem. Eng. Data 30 (4): 376–379. doi:10.1021/je00042a003.
^ Desmarais, WT et al. (2002). "The 1.20 Å resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with Tris: A tale of buffer inhibition". Structure 10 (8): 1063–1072. doi:10.1016/S0969-2126(02)00810-9. PMID 12176384.
^ Ghalanbor, Z et al. (2008). "Binding of Tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity". Protein Peptide Lett. 15 (2): 212–214. doi:10.2174/092986608783489616. PMID 18289113.
^ Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". doi:10.1002/14356007.a17_401.
^ Irvin, R.T.; MacAlister, T.J.; Costerton, J.W. (1981). "Tris(hydroxymethyl)aminomethane Buffer Modification of Escherichia coli Outer Membrane Permeability". J. Bacteriol 145 (3): 1397–1403.
^ Kallet, RH; Jasmer RM; Luce JM et al. (2000). "The treatment of acidosis in acute lung injury with tris-hydroxymethyl aminomethane (THAM)". American Journal of Respiratory and Critical Care Medicine 161 (4): 1149–1153. doi:10.1164/ajrccm.161.4.9906031. PMID 10764304.
^ Hoste, EA; Colpaert, K; Vanholder, RC; Lameire, NH; De Waele, JJ; Blot, SI; Colardyn, FA (2005). "Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis.". Journal of nephrology 18 (3): 303–7. PMID 16013019.

UpToDate Contents

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1. 乳酸アシドーシスにおける重炭酸療法 bicarbonate therapy in lactic acidosis
2. 成人における代謝性アシドーシスへのアプローチ approach to the adult with metabolic acidosis
3. 高二酸化炭素血症の許容（Permissive hypercapnia） permissive hypercapnia
4. 経腟分娩後の出血管理 management of postpartum hemorrhage at vaginal delivery
5. 産褥性子宮内反症 puerperal uterine inversion

English Journal

A comparison of oxytocin and carboprost tromethamine in the prevention of postpartum hemorrhage in high-risk patients undergoing cesarean delivery.

Bai J, Sun Q, Zhai H.Author information Department of Gynecology and Obstetrics, Jinan Maternity and Child Care Hospital, Jinan, Shandong 250001, P.R. China.AbstractThe aim of this study was to compare carboprost with oxytocin for the prevention of postpartum hemorrhage (PPH) in females with a high risk of PPH undergoing cesarean delivery. Patients were randomly divided into three groups that received different uterotonics (oxytocin, carboprost and oxytocin plus carboprost) during cesarean section, following the delivery of the infant. A total of 117 females (age range, 19-40 years) at 35-40 weeks gestation who delivered by cesarean between December, 2010 and May, 2012 were included in this study. There were 29 cases of twins, 12 cases of polyhydramnios, 23 cases of placenta previa and 53 cases of fetal macrosomia. There were 37 patients in the oxytocin group, 36 in the carboprost group and 44 in the oxytocin plus carboprost group. No significant differences were identified in maternal age, gravidity/parity, gestational age and reason for cesarean delivery between the three groups. The median blood loss in the oxytocin, carboprost and oxytocin plus carboprost groups was 610, 438 and 520 ml, respectively. The blood loss in the carboprost group was significantly lower than that in the oxytocin and oxytocin plus carboprost groups (both P<0.05). Vomiting occurred in eight patients from the carboprost group, two from the oxytocin group and two from the oxytocin plus carboprost group (P=0.036). Carboprost was more effective than oxytocin in preventing PPH in high-risk patients undergoing cesarean delivery.
Experimental and therapeutic medicine.Exp Ther Med.2014 Jan;7(1):46-50. Epub 2013 Nov 1.
The aim of this study was to compare carboprost with oxytocin for the prevention of postpartum hemorrhage (PPH) in females with a high risk of PPH undergoing cesarean delivery. Patients were randomly divided into three groups that received different uterotonics (oxytocin, carboprost and oxytocin plu
PMID 24348762

Characteristics of urinary tract infection pathogens and their in vitro susceptibility to antimicrobial agents in China: data from a multicenter study.

Qiao LD, Chen S, Yang Y, Zhang K, Zheng B, Guo HF, Yang B, Niu YJ, Wang Y, Shi BK, Yang WM, Zhao XK, Gao XF, Chen M, Tian Y.Author information Department of Urology, Beijing Tongren Hospital Capital Medical University, Beijing, China.AbstractOBJECTIVE: This study assessed the characteristics of pathogens identified in clinical isolates from patients with urinary tract infection (UTI) and their in vitro sensitivity to commonly used antibiotics in the clinical setting in China.
BMJ open.BMJ Open.2013 Dec 13;3(12):e004152. doi: 10.1136/bmjopen-2013-004152.
OBJECTIVE: This study assessed the characteristics of pathogens identified in clinical isolates from patients with urinary tract infection (UTI) and their in vitro sensitivity to commonly used antibiotics in the clinical setting in China.DESIGN AND SETTING: Multicenter study was conducted between Ja
PMID 24334199

Reduction of Interleukin 8 and Platelet-Derived Growth Factor Levels by Topical Ketorolac, 0.45%, in Patients With Diabetic Retinopathy.

Schoenberger SD, Kim SJ, Shah R, Sheng J, Cherney E.Author information Vanderbilt Eye Institute, Vanderbilt University Medical Center, Nashville, Tennessee.AbstractIMPORTANCE Inhibition of inflammatory cytokines may have therapeutic effects in diabetic retinopathy (DR). OBJECTIVE To compare aqueous and vitreous levels of 17 inflammatory cytokines in patients treated preoperatively with topical ketorolac tromethamine, 0.45%, or placebo before pars plana vitrectomy for complications related to proliferative DR (PDR). DESIGN, SETTING, AND PARTICIPANTS A prospective, randomized, placebo-controlled, patient-masked interventional study performed in a university academic hospital included 20 eyes from 20 patients undergoing pars plana vitrectomy for complications of PDR. INTERVENTIONS Eyes were randomized to ketorolac tromethamine, 0.45% (Acuvail), or placebo 4 times daily for 3 days before pars plana vitrectomy. Undiluted aqueous and vitreous samples were taken at the time of surgery and immediately frozen at -80°C. MAIN OUTCOMES AND MEASURES Aqueous and vitreous levels of prostaglandin E2 and 16 other inflammatory cytokines implicated in the pathogenesis of DR. RESULTS Prostaglandin E2, platelet-derived growth factor (PDGF) AA, eotaxin, vascular endothelial growth factor, interferon γ-inducible protein of 10 kDa, monocyte chemoattractant protein 1, growth-related oncogene, interleukin 6, interleukin 8 (IL-8), and tumor necrosis factor were detectable in the aqueous and vitreous of at least half of the eyes, and these cytokines were analyzed further. Aqueous levels were lower in the ketorolac group for all cytokines detected, but only the difference in IL-8 was statistically significant (52% reduction; P = .04). Levels of IL-8 (41% reduction; P = .002) and PDGF-AA (21% reduction; P = .009) were significantly lower in the vitreous of patients treated with ketorolac. CONCLUSIONS AND RELEVANCE Topical ketorolac tromethamine, 0.45%, significantly lowered aqueous IL-8 levels and vitreous IL-8 and PDGF-AA levels in this series of eyes, suggesting that it may cause meaningful inhibition of inflammatory cytokines implicated in the pathogenesis of DR. TRIAL REGISTRATION clinicaltrials.gov Identifier: NCT01609881.
JAMA ophthalmology.JAMA Ophthalmol.2013 Dec 12. doi: 10.1001/jamaophthalmol.2013.6203. [Epub ahead of print]
IMPORTANCE Inhibition of inflammatory cytokines may have therapeutic effects in diabetic retinopathy (DR). OBJECTIVE To compare aqueous and vitreous levels of 17 inflammatory cytokines in patients treated preoperatively with topical ketorolac tromethamine, 0.45%, or placebo before pars plana vitrect
PMID 24336915

Japanese Journal

Design and Evaluation of Bioadhesive in-Situ Nasal Gel of Ketorolac Tromethamine

Chelladurai Sankar,Mishra Madhusmita,Mishra Brahmeshwar
Chemical & pharmaceutical bulletin 56(11), 1596-1599, 2008-11-01
… The present study was aimed at developing safe and effective bioadhesive gelling systems of ketorolac tromethamine, a potent non-narcotic analgesic with moderate anti-inflammatory activity for nasal systemic delivery. … The anti-inflammatory activity and mucosal irritancy of selected gels were also evaluated in rats and these results were compared with per oral, intraperitoneal and nasal solution administration of ketorolac tromethamine. …
NAID 110006968063

Enhanced Electrochemical Detection of Ketorolac Tromethamine at Polypyrrole Modified Glassy Carbon Electrode

Santhosh Padmanabhan,Senthil Kumar Nagarajan,Renukadevi Murugesan [他],GOPALAN Anantha Iyengar,VASUDEVAN Thiyagarajan,LEE Kwang-Pill
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 23(4), 475-478, 2007-04-10
NAID 10018914445

犬の開花期黄体に及ぼすPGF_<2α>-analogue(Etiproston tromethamine)投与の影響(臨床繁殖学)

桐原信之,永縄敦子,堀達也 [他],河上栄一,筒井敏彦
The journal of veterinary medical science 67(1), 1-6, 2005-01-25
犬において,黄体退行による流産および分娩誘起,子宮蓄膿症の治療などに各種PGF_<2α>-analogue(PGA)が使用されている.しかし,犬の臨床に副作用の少ない,最も適したPGAを検索している段階である.そこで,犬では未検討であるPGAのetiprostontromethamine(PGA-E)について,犬で比較的多く使用されているcloprostenol(PGA-C)をコントロ …
NAID 110003963664

Related Pictures

★リンクテーブル★

リンク元	「トロメタミン」「trometamol」「Tris buffer」「THAM」
拡張検索	「dinoprost tromethamine」

「トロメタミン」

Tris
Names
	IUPAC name 2-Amino-2-hydroxymethyl-propane-1,3-diol
	Other names TRIS, Tris, Tris base, Tris buffer, Trizma, Trisamine, THAM, Tromethamine, Trometamol, Tromethane, Trisaminol
Identifiers
CAS Registry Number	77-86-1
ATC code	B05BB03; B05XX02
ChEBI	CHEBI:9754
ChEMBL	ChEMBL1200391
ChemSpider	6257
	InChI InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2 ; Key: LENZDBCJOHFCAS-UHFFFAOYSA-N ; InChI=1/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2; Key: LENZDBCJOHFCAS-UHFFFAOYAN ;
IUPHAR/BPS	7328
Jmol-3D images	Image
KEGG	D00396
PubChem	6503
RTECS number	TY2900000
	SMILES OCC(N)(CO)CO ;
UNII	023C2WHX2V
Properties
Chemical formula	C4H11NO3
Molar mass	121.14 g·mol−1
Appearance	White crystalline powder
Density	1.328g/cm3
Melting point	>175-176 °C (448-449 K)
Boiling point	219 °C (426 °F; 492 K)
Solubility in water	~50 g/100 mL (25 °C)
Acidity (pKa)	8.07
Hazards
Main hazards	Irritant
Safety data sheet	External MSDS
R-phrases	R36 R37 R38
S-phrases	S26 S36
NFPA 704	2
Flash point	Non-flammable
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references