甲胺 | 74-89-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 甲胺
• 中文别名: 氨基甲烷；一甲胺(无水)；伯胺；无水一甲胺；一甲胺
• 英文名称: methylamine
• 英文别名: Methanamine；monomethylamine；MeNH2；N-methylamine；methyl ammonia；aminomethane
• CAS: 74-89-5
• 化学式: CH₅N
• 分子量: 31.0574
• InChiKey: BAVYZALUXZFZLV-UHFFFAOYSA-N

物化性质

• 物理描述：
  Methylamine, anhydrous appears as a colorless gas or a liquid. Pungent fishy odor resembling odor of ammonia. The liquid boils at 20.3°F hence vaporizes rapidly when unconfined. Vapors are heavier than air and may collect in low-lying areas. Easily ignited under most conditions. Under prolonged exposure to intense heat the containers may rupture violently and rocket. Used for making pharmaceuticals, insecticides, paint removers, surfactants, rubber chemicals.
• 颜色/状态：
  Colorless gas [Note: A liquid below 21 degrees F. Shipped as a liquefied compressed gas]
• 气味：
  Fish or ammonia-like odor
• 沸点：
  -6.3 °C
• 熔点：
  -93.4 °C
• 闪点：
  -10 °C (14 °F) - closed cup /Methylamine solution 30-50%/
• 溶解度：
  1 volume of water at 12.5 °C dissolves 1154 volumes of gas; at 25 °C dissolves 959 volumes of gas; 10.5 g is contained in 100 mL saturated benzene solution
• 密度：
  0.6624 g/cu cm at 25 °C; 0.0014 g/cu cm at 101.33 kPa
• 蒸汽密度：
  Saturated vapor density: 0.21270 lb/cu ft at 60 °F (Methylamine, anhydrous)
• 蒸汽压力：
  2.65X10+3 mm Hg at 25 °C
• 亨利常数：
  1.11e-05 atm-m3/mole
• 大气OH速率常数：
  2.20e-11 cm3/molecule*sec
• 稳定性/保质期：

  1、甲胺水溶液或醇溶液均为易燃液体。由于闪点低，容易挥发，有毒，并能与空气形成爆炸性混合物，应避免日光直射和使用可能产生静电的设备。甲胺对铜或铜合金、铝、锡以及镀锌铁板有腐蚀作用，且具有易燃性。

  2、化学性质方面，甲胺展现出典型的伯胺反应：

  • 其水溶液呈碱性，能与无机酸、有机酸及芳香族硝基化合物等物质反应生成具有一定熔点的盐类。与铜、银等重金属氯化物也能形成络合盐。
  • 与酰氯或酸酐进行酰基化反应，可生成N-取代酰胺；与羧酸生成的盐再经过脱水处理也能生成N-取代酰胺。与苯磺酰氯反应，则能生成N-取代苯磺酰胺。
  • 可以与卤代烃、醇、酚或胺盐等烃基化试剂作用，氮原子上的氢可被烃基所取代。
  • 能够与氰酸、二硫化碳、腈类化合物及环氧化物发生加成反应。
  • 在伯胺与脂肪族或芳香族物质进行反应时，脱水生成Schiff碱。
  • 对于酸性高锰酸钾而言，甲胺较为稳定；然而，它容易被碱性高锰酸钾所氧化，生成醛或羧酸。在过硫酸、过氧化氢及有机过氧酸的作用下，则可得到含氧化合物的胺类化合物。
  • 在与亚硝酸反应时能够定量地生成氮气。
  • 加热条件下，甲胺与氯仿和氢氧化钾醇溶液共同作用可生成异腈。
  • 与Grignard试剂反应可生成烃类物质。

  此外，在高温（550~670℃）下发生热解，生成氨、氰化氢、甲烷、氢气以及氮气等产物。在紫外光照射下也能分解产生甲烷和氮气气体及液体。

  3. 稳定性：稳定

  4. 禁配物：酸类、卤素、酸酐、强氧化剂、氯仿

  5. 聚合危害：不聚合

  6. 分解产物：氨

• 自燃温度：
  806 °F (430 °C)
• 分解：
  Hazardous decomposition products formed under fire conditions: Carbon oxides, nitrogen oxides (NOx) /Methylamine solution 30-50%/
• 腐蚀性：
  Corrosive to copper, copper alloys, zinc alloys, aluminum, and galvanized surfaces (Methylamine solution)
• 燃烧热：
  -1085.6 kJ/mole at 25 °C (gas)
• 汽化热：
  Molar enthalpy of vaporization at 25 °C: 23.37 kJ/mol
• 表面张力：
  19.15 mN/m at 25 °C
• 电离电位：
  8.97 eV
• 气味阈值：
  The odor of methylamine is faint but readily detectable at less than 10 ppm, becomes strong at from 20 to 100 ppm and intolerably ammoniacal at 100 to 500 ppm.
• 解离常数：
  pKa = 10.66 at 25 °C
• 保留指数：
  305 ;380 ;328

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  2
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

代谢

目的：有人声称口服肌酸补充剂可能会通过增加甲基胺和甲醛的产生而对健康消费者产生潜在的细胞毒性作用。尽管有这种说法，但至今没有科学证据在人类身上得到证实或反驳这种广泛使用的增进体能物质的这种有害效果。方法：二十名年轻健康的男性连续14天每天摄入21克肌酸一水合物。在补充剂使用前后的第14天收集静脉血样本和24小时尿液。在血浆和尿液中分析肌酸和肌酐，并在24小时尿样中测定甲基胺、甲醛和甲酸。结果：口服肌酸补充剂使血浆肌酸含量增加了7.2倍（P < 0.001），尿液排出量增加了141倍（P < 0.001），但对肌酐水平没有影响。在肌酸喂养后，24小时尿液中甲基胺和甲醛的排泄分别增加了9.2倍（P = 0.001）和4.5倍（P = 0.002），但尿液中白蛋白排出量没有增加（肌酸喂养前9.78 +/- 1.93 mg/24小时，肌酸喂养后6.97 +/- 1.15 mg/24小时）。结论：这项调查表明，短期、高剂量的口服肌酸补充剂增加了潜在细胞毒性化合物的排泄，但对肾脏通透性没有不良影响。这为肾小球微血管病缺失提供了间接证据。

PURPOSE: It has been claimed that oral creatine supplementation might have potential cytotoxic effects on healthy consumers by increasing the production of methylamine and formaldehyde. Despite this allegation, there has been no scientific evidence obtained in humans to sustain or disprove such a detrimental effect of this widely used ergogenic substance. METHODS: Twenty young healthy men ingested 21 g of creatine monohydrate daily for 14 consecutive days. Venous blood samples and 24-hr urine were collected before and after the 14th day of supplementation. Creatine and creatinine were analyzed in plasma and urine, and methylamine, formaldehyde, and formate were determined in 24-hr urine samples. RESULTS: Oral creatine supplementation increased plasma creatine content 7.2-fold (P < 0.001) and urine output 141-fold (P < 0.001) with no effect on creatinine levels. Twenty-four-hour urine excretion of methylamine and formaldehyde increased, respectively, 9.2-fold (P = 0.001) and 4.5-fold (P = 0.002) after creatine feeding, with no increase in urinary albumin output (9.78 +/- 1.93 mg/24 hr before, 6.97 +/- 1.15 mg/24 hr creatine feeding). CONCLUSION: This investigation shows that short-term, high-dose oral creatine supplementation enhances the excretion of potential cytotoxic compounds, but does not have any detrimental effects on kidney permeability. This provides indirect evidence of the absence of microangiopathy in renal glomeruli.

来源:Hazardous Substances Data Bank (HSDB)

代谢

单甲基胺和三甲基胺在体内被转化为二甲胺。

Mono- and trimethylamines are converted to dimethylamine in the body.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在碳限制连续培养中，对Arthobacter P1中甲基胺和甲醛代谢的调控进行了研究。获得了证据表明，在这个生物体中，将甲基胺转化为甲醛以及甲醛固定的酶的合成是依次诱导的。

The regulation of methylamine and formaldehyde metabolism in Arthobacter P1 was investigated in carbon-limited continuous cultures. Evidence was obtained that the synthesis of enzymes involved in the conversion of methylamine into formaldehyde and in formaldehyde fixation is induced sequentially in this organism.

来源:Hazardous Substances Data Bank (HSDB)

代谢

甲基胺在大鼠体内的代谢已被研究，以阐明单胺氧化酶和肠道细菌在化合物代谢中的作用。在一系列实验中，先单独或联合给予短效和长效单胺氧化酶抑制剂，然后注射甲基(14)C胺盐酸盐，通过检测呼出气和尿液中放射性物质的排泄，间接评估单胺氧化酶在甲基胺代谢中的作用。数据...提供了间接证据，证明异烟肼（一种抑制甲基胺氧化的抑制剂）的作用是通过与被其他研究者提出的作为甲基胺代谢主要贡献者的MAO系统不同的酶系统介导的。肠道中甲基胺的细菌氧化在化合物的整体代谢中只起到较小的作用。

The metabolism of methylamine has been investigated in the rat in order to elucidate the role of monoamine oxidase and intestinal bacteria in the metabolism of the compound. In a series of experiments in which short and long acting inhibitors of monoamine oxidase were administered either alone or in combination prior to methyl (14)C amine hydrochloride injection, the excretion of radioactivity in the expired air and the urine was examined to indirectly assess the role of monoamine oxidase in the metabolism of methylamine. The data ... provide indirect evidence to demonstrate that the effect of iproniazid, an inhibitor of methylamine oxidation, is mediated through enzyme systems separate from MAO systems which have been invoked as major contributors to metabolism of methylamine by other investigators. The bacterial oxidation of methylamine in the intestine plays a minor role in the overall metabolism of the compounds.

来源:Hazardous Substances Data Bank (HSDB)

代谢

尿素毒素往往会因为饮食过量或者肾脏过滤功能不佳而在血液中积聚。大多数尿素毒素是代谢废物，通常通过尿液或粪便排出。

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

识别和使用：甲基胺是一种无色气体。在21华氏度以下为液体。作为液化压缩气体运输。它用作加速剂、染料、药品、杀虫剂、杀菌剂、表面活性剂、制革、醋酸纺织品的染色、燃料添加剂、聚合抑制剂、油漆去除剂成分、溶剂、摄影显影剂、火箭推进剂的中介。人类研究：容易产生嗅觉疲劳。短暂接触20至100 ppm会产生暂时的眼睛、鼻子和喉咙刺激。在低于10 ppm的较长时间接触下不会产生刺激症状。一名工人在接触2至60 ppm甲基胺的浓度下报告了过敏性或化学性支气管炎，并在大约25 ppm时注意到一些刺激。甲基胺抑制表皮生长因子、胰岛素和血清刺激人类成纤维细胞培养中DNA合成的刺激作用。动物研究：将40%水溶液的甲基胺0.1 mL涂抹在豚鼠皮肤上会导致坏死。液化的甲基胺在几分钟内导致豚鼠皮肤颜色变化、肿胀和呈紫色，48小时后变灰和坏死。12天后，新鲜肉芽组织出现，被无毛囊的扁平表皮覆盖。将5%水溶液的一滴应用于动物眼睛导致结膜出血、角膜浅层浑浊和水肿。甲基胺在大鼠中引起间质性肺炎，进而发展为纤维化。在鼠淋巴瘤细胞试验中，甲基胺在遗传毒性测试中呈阳性。在含有和不含有代谢活化的鼠伤寒沙门氏菌菌株（TA1535、TA1537、TA97、TA98和TA100）中，甲基胺在遗传毒性测试中呈阴性。甲基胺从胺分解中内源性产生，在某些病理条件下，包括糖尿病，其组织水平升高。甲基胺是一种内源性脂肪胺，在小鼠中具有厌食性质。甲基胺对摄食的影响取决于下丘脑释放的一氧化氮和多巴胺。生态毒性：从斑马鱼（Brachydanio rerio）中分离出的单个受精卵可以在体外发育，以阐明可能对胚胎发生的危害。甲基胺在0.1 - 5 mg/mL孵化介质浓度下，通过细胞毒性作用在24期基本导致大多数卵的死亡。未观察到畸形。

IDENTIFICATION AND USE: Methylamine is colorless gas. A liquid below 21 degrees F. Shipped as a liquefied compressed gas. it is used as an intermediate for accelerators, dyes, pharmaceuticals, insecticides, fungicides, surface active agents, tanning, dyeing of acetate textiles, fuel additive, polymerization inhibitor, component of paint removers, solvent, photographic developer, rocket propellant. HUMAN STUDIES: Olfactory fatigue occurs readily. Brief exposures to 20 to 100 ppm produce transient eye, nose, and throat irritation. No symptoms of irritation are produced from longer exposures at less than 10 ppm. Allergic or chemical bronchitis was reported in a worker exposed to methylamine at concentrations ranging from 2 to 60 ppm, and some irritation was noted at about 25 ppm. Stimulation of DNA synthesis in human fibroblast cultures by epidermal growth factor, insulin, and serum is inhibited by methylamine. ANIMAL STUDIES: Application of 0.1 mL of a 40% aqueous solution of methylamine to the skin of a guinea pig caused necrosis. Liquified methylamine caused change in guinea pig skin color with swelling and purple hue within a few minutes, gray and necrotic in 48 hr. At 12 days fresh granulation tissue had appeared covered by flat epidermis with no hair follicles. A drop of 5% solution in water applied to animal eyes caused hemorrhages in the conjunctiva, superficial corneal opacities, and edema. Methylamine caused interstitial pneumonitis progressing to fibrosis in rats. Methylamine was positive when tested for genotoxicity in a mouse lymphoma cell assay. Methylamine was negative when tested for genotoxicity in Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of metabolic activation. Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. Methylamine is an endogenous aliphatic amine exhibiting anorexigenic properties in mice. The effects of methylamine on feeding depend on the hypothalamic release of nitric oxide and dopamine. ECOTOXICITY: Isolated individual fertilized eggs from zebrafish (Brachydanio rerio) developed in vitro can be used to elucidate possible actions of hazardous agents on embryogenesis. Methylamine at concentration 0.1 - 5 mg/mL incubation media caused mortality of most of eggs by cytotoxic effects essentially at stage 24. Malformations were not observed.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

尿毒症毒素如甲基胺通过有机离子转运体（特别是OAT3）被积极运输到肾脏中。尿毒症毒素水平的增加可以刺激活性氧种类的产生。这似乎是通过尿毒症毒素直接结合或抑制NADPH氧化酶（特别是肾脏和心脏中丰富的NOX4）来介导的（A7868）。活性氧种类可以诱导几种不同的DNA甲基转移酶（DNMTs），这些酶参与沉默一种被称为KLOTHO的蛋白质。KLOTHO已被确定在抗衰老、矿物质代谢和维生素D代谢中具有重要作用。许多研究表明，在急性或慢性肾脏疾病中，由于局部活性氧种类水平升高，KLOTHO mRNA和蛋白质水平会降低（A7869）。

Uremic toxins such as methylamine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

长期暴露于尿毒症毒素可能会导致多种疾病，包括肾脏损伤、慢性肾病和心血管疾病。

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

该物质可以通过吸入被身体吸收。

The substance can be absorbed into the body by inhalation.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

吸收、分配和排泄

甲基胺可以通过半碳酰胺敏感的胺氧化酶（SSAO）转化为甲醛和过氧化氢，这些物质已被证实对培养的内皮细胞具有毒性。/作者/研究了这些来自甲基胺的脱氨产物是否会在体内产生潜在的有害毒性效应。在小鼠给药[14C]-甲基胺后，不同组织中检测到了持久的残留放射性。甚至在注射[14C]-甲基胺后5天，仍可检测到大约10%的总给药放射性。通过高度选择性的SSAO抑制剂，（E）-2-(4-氟苯乙基)-3-氟丙烯胺盐酸盐（MDL-72974A），可以阻断80%的不可逆加合物的形成。残留放射性主要与不溶性组织成分和可溶性大分子相关。放射性标记的大分子在酶促蛋白水解后被分解。结果表明，来自甲基胺的甲醛在体内与蛋白质发生相互作用。在链脲佐菌素诱导的糖尿病小鼠中，发现肾脏中的SSAO活性和残留放射性的形成显著增加。长期给药甲基胺会增强血液中的前肾素水平，这强烈表明甲基胺的失控脱氨可能是引发内皮损伤和随后动脉粥样硬化发生的风险因素。

Methylamine can be converted by semicarbazide-sensitive amine oxidase (SSAO) to formaldehyde and hydrogen peroxide, which have been proven to be toxic towards cultured endothelial cells. /The authors/ investigated whether or not these deaminated products from methylamine can exert potentially hazardous toxic effects in vivo. Long lasting residual radioactivity in different tissues was detected following administration of [14C]-methylamine in the mouse. Approximately 10% of the total administered radioactivity could even be detected 5 days after injection of [14C]-methylamine. Eighty percent of the formation of irreversible adducts can be blocked by a highly selective SSAO inhibitor, (E)-2-(4-fluorophenethyl)-3-fluoroallylamine hydrochloride (MDL-72974A). The residual radioactivity was primarily associated with the insoluble tissue components and the soluble macromolecules. Radioactively labelled macromolecules were fragmented following enzymatic proteolysis. Results suggest that the formaldehyde derived from methylamine interacts with proteins in vivo. In the streptozotocin-induced diabetic mice, both SSAO activity and the formation of residual radioactivity were found to be significantly increased in the kidney. Chronic administration of methylamine enhances blood prorenin level, which strongly suggests that uncontrolled deamination of methylamine may be a risk factor for initiation of endothelial injury, and subsequent genesis of atherosclerosis.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

/MILK/ ...在人类母乳和羊水中测量挥发性脂肪胺的存在...以评估它们在新生儿高胃泌素血症中的作用。这些挥发性含氮氨基酸代谢物之前已被证明能在体内和体外实验准备中刺激胃泌素的释放。...目前的研究...表明，在分娩后的前几周内，母乳中存在显著浓度的这些刺激胃泌素的挥发性胺，羊水中也有。在母乳和羊水样本中确定的个别胺类包括甲基胺、二甲胺、乙胺、三甲胺、丙胺、异丁胺和丁胺。这项研究提供了间接证据，支持胎儿/新生儿在出生前后的短时间内测得的高胃泌素血症可能是由于摄入了含有高浓度刺激胃泌素胺的液体。

/MILK/ ...The presence of volatile aliphatic amines ... in human breast milk and amniotic fluid /was measured/ to assess their role in neonatal hypergastrinemia. These volatile nitrogenous amino acid metabolites have been previously demonstrated to stimulate gastrin release in in vivo and in vitro laboratory preparations. ... The present study ... demonstrated that these gastrin-stimulatory volatile amines were present in significant concentrations in breast milk during the first several weeks after parturition and in amniotic fluid. The individual amines that were identified in both human milk and amniotic fluid samples were methylamine, dimethylamine, ethylamine, trimethylamine, propylamine, isobutylamine, and butylamine. This study provides indirect evidence to support the possibility that the hypergastrinemia measured in the fetus/neonate during the period immediately before and after birth may be attributable, in part, to the ingestion of fluid containing high concentrations of gastrin-stimulating amines.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

背景：目前，透析充分性是通过尿素清除率来评判的。然而，尿素相对无毒，并且具有与其他大量保留溶质不同的特性。特别是，细胞内隔离的溶质可能与尿素表现不同。方法：我们使用高效液相色谱法（HPLC）研究了这类物质的一个例子，即脂肪族胺单甲基胺（MMA），在稳定的血液透析门诊患者（n = 10）中的情况。结果：终末期肾病患者的平均MMA水平在透析前为76 +/- 15微克/升，而正常受试者（n = 10）为32 +/- 4微克/升（P < 0.001）。平均尿素减少率为62%，而MMA的减少率为43%（P < 0.01）。MMA水平在透析后1小时反弹到基线的85%，而尿素水平仅反弹到基线的47%。MMA的计算分布体积远大于尿素，这与细胞内隔离一致。红细胞内MMA浓度的测量证实红细胞中的水平高于血浆，比率为4.9:1。由于MMA的细胞内隔离，我们计算了从全血中移除的MMA的清除率。尿素的清除率平均为222 +/- 41毫升/分钟，MMA为121 +/- 14毫升/分钟，而血浆中肌酐的清除率为162 +/- 20毫升/分钟（P < 0.01，对于所有差异）。使用体外透析，在没有红细胞的情况下，溶质清除率相似：尿素、肌酐和MMA分别为333 +/- 6、313 +/- 8和326 +/- 4毫升/分钟。这些发现表明，MMA在体内的清除率相对于肌酐较低是由于MMA进入透析器血液路径中的红细胞，从而减少了透析对其的移除。结论：总之，我们发现，在常规血液透析中，MMA的清除效率不如尿素或肌酐，并且红细胞可能会限制其透析，不仅是由于未能释放它，而且还可能在血液通过透析器时进一步隔离它。

BACKGROUND: Dialysis adequacy is currently judged by measures of urea clearance. However, urea is relatively non-toxic and has properties distinct from large classes of other retained solutes. In particular, intracellularly sequestered solutes are likely to behave differently than urea. METHODS: We studied an example of this class, the aliphatic amine monomethylamine (MMA), in stable hemodialysis outpatients (n = 10) using an HPLC-based assay. RESULTS: Mean MMA levels pre-dialysis in end-stage renal disease subjects were 76 +/- 15 ug/L compared to 32 +/- 4 ug/L in normal subjects (n = 10) (P < 0.001). Mean urea reduction was 62% while the reduction ratio for MMA was 43% (P < 0.01). MMA levels rebounded in the 1 hour post-dialytic period to 85% of baseline, whereas urea levels rebounded only to 47% of baseline. MMA had a much larger calculated volume of distribution compared to urea, consistent with intracellular sequestration. Measures of intra-red blood cell (RBC) MMA concentrations confirmed greater levels in RBCs than in plasma with a ratio of 4.9:1. Because of the intracellular sequestration of MMA, we calculated its clearance using that amount removed from whole blood. Clearances for urea averaged 222 +/- 41 mL/min and for MMA 121 +/- 14 mL/min, while plasma clearance for creatinine was 162 +/- 20 mL/min (P < 0.01, for all differences). Using in vitro dialysis, in the absence of RBCs, solute clearance rates were similar: 333 +/- 6, 313 +/- 8 and 326 +/- 4 mL/min for urea, creatinine and MMA, respectively. These findings suggest that the lower MMA clearance relative to creatinine in vivo is a result of MMA movement into RBCs within the dialyzer blood path diminishing its removal by dialysis. CONCLUSION: In conclusion, we find that, in conventional hemodialysis, MMA is not cleared as efficiently as urea or creatinine and raise the possibility that RBCs may limit its dialysis not merely by failing to discharge it, but by further sequestering it as blood passes through the dialyzer.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在这项研究中，我们检查了两种肌酸单水合物补充方案对24小时尿肌酸和甲基胺排泄的影响。九名男性参与者完成了两个试验，间隔6周。在一个试验中，参与者连续5天每天摄入4次，每次5克的肌酸单水合物，而在另一个试验中，他们连续5天每天摄入20次，每次1克的肌酸单水合物。我们在2个基线日（第1-2天）、5天补充期间（第3-7天）以及补充后2天（第8-9天）收集了24小时尿液样本。使用高效液相色谱法检测尿液中的肌酸，使用气相色谱法检测甲基胺。与4次5克/天的方案（62.32 +/- 9.36克）相比，20次1克/天的方案排泄的肌酸较少（49.25 +/- 10.53克）（平均值 +/- 标准差；P < 0.05）。在补充期间的第3-7天，甲基胺的平均总排泄量（n = 6）在20次1克/天和4次5克/天的方案中分别为8.61 +/- 7.58毫克和24.81 +/- 25.76毫克（P < 0.05）。使用20次1克/天剂量排泄的肌酸较少，这表明肌酸在体内，最可能在肌肉中的保留更多。较低剂量和更频繁的肌酸单水合物补充似乎能进一步减少甲基胺的形成。

In this study, we examined the effect of two creatine monohydrate supplementation regimes on 24-hr urinary creatine and methylamine excretion. Nine male participants completed two trials, separated by 6 weeks. Participants ingested 4 x 5 g x day(-1) creatine monohydrate for 5 days in one trial and 20 x 1 g x day(-1) for 5 days in the other. We collected 24-hr urine samples on 2 baseline days (days 1-2), during 5 days of supplementation (days 3-7), and for 2 days post-supplementation (days 8-9). Urine was assayed for creatine using high-performance liquid chromatography and methylamine using gas chromatography. Less creatine was excreted following the 20 x 1 g x day(-1) regime (49.25 +/- 10.53 g) than the 4 x 5 g x day(-1) regime (62.32 +/- 9.36 g) (mean +/- s; P < 0.05). Mean total excretion of methylamine (n = 6) over days 3-7 was 8.61 +/- 7.58 mg and 24.81 +/- 25.76 mg on the 20 x 1 g x day(-1) and 4 x 5 g x day(-1) regimes, respectively (P < 0.05). The lower excretion of creatine using 20 x 1 g x day(-1) doses suggests a greater retention in the body and most probably in the muscle. Lower and more frequent doses of creatine monohydrate appear to further attenuate formation of methylamine.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 安全说明：
  S16,S26,S29,S3,S3/7,S33,S36/37,S36/37/39,S39,S45,S7
• 危险品运输编号：
  UN 3286 3/PG 2
• WGK Germany：
  2
• 海关编码：
  2921110090
• 危险类别：
  3
• 危险品标志：
  Xn
• 危险类别码：
  R37/38,R12,R41,R20
• RTECS号：
  PF6300000
• 包装等级：
  II
• 危险标志：
  GHS02,GHS05,GHS07
• 危险性描述：
  H225,H314,H335
• 危险性防范说明：
  P210,P280,P303 + P361 + P353,P304 + P340 + P310,P305 + P351 + P338,P403 + P235

SDS

第一部分：化学品名称

制备方法与用途

制备方法： 在工业生产中，甲胺是通过将甲醇和氨在高温下通入装有活性氧化铝催化剂的转化器来合成的。虽然甲基化反应不会仅限于一甲胺阶段，但所得产物是一甲胺、二甲胺和三甲胺的混合物。为增加一甲胺和二甲胺的比例，需使氨过量并加入水进行循环。当氨是甲醇的2.5倍，且反应温度控制在425℃、压力保持在2.45MPa时，可得到10-12%的一甲胺、8-9%的二甲胺和11-13%的三甲胺混合物。由于三甲胺与氨及其他甲胺在常压下形成共沸物，分离方法通常采用加压精馏和萃取精馏相结合的方式。据文献报道，改变甲醇和氨的比例是获得理想产品的有效手段，其中甲醇与氨的比例为1:1.5时适合生成三甲胺，而比例为1:4时适合生成一甲胺。

精制方法： 甲胺中通常会含有二甲胺、三甲胺、甲醇及氨等杂质。首先可将甲胺水溶液进行萃取蒸馏以去除三甲胺，随后通过分馏除去二甲胺。另外，也可以采用以下步骤：将甲胺盐酸盐用干燥的氯仿萃取30小时以上，以去除高级胺，并使用乙醇进行重结晶（熔点225~226℃）精制。另一方法是先将甲胺与甲醛生成的缩合物进行分馏，然后在丁醇中用盐酸分解所得盐酸盐并再次用乙醇重结晶。此过程中的精制甲胺盐酸盐需使用过量的氢氧化钾或氢氧化钠分解以得到气态甲胺，并通过固体氢氧化钾脱水后，利用氧化银去除微量氨。最后，使用干冰-乙醚冷却液化，再用芴酮钠干燥即可获得纯净的甲胺。其他精制方法包括将甲胺盐酸盐用丁醇、无水乙醇或甲醇与氯仿混合物进行重结晶，并用氯仿洗涤以除去微量二甲胺盐酸盐，最后在真空干燥器中干燥。

水溶液： 40%的甲胺水溶液可以用水稀释为30%甲胺溶液。

用途简介： 甲胺广泛应用于橡胶硫化促进剂、染料、医药、杀虫剂以及表面活性剂的合成等领域。

反应信息

• 作为反应物：
  描述：

  甲胺 以 neat (no solvent) 为溶剂， 生成 氢氰酸
  参考文献：
  名称：

  HCN 在 14 μm 区域的傅里叶变换光谱

  摘要：

  摘要 使用美国国家太阳天文台傅里叶变换光谱仪以约 0.005 cm -1 的分辨率测量了 HCN 各种同位素的 710-cm -1 谱带。分析了六个 HCN 波段、一个 H 13 CN 波段和一个 HC 15 N 波段以获得准确的波段原点和旋转常数。对于大多数波段，计算的波段原点的精度优于 0.0003 cm -1。通过与模拟的比较，已经从这些光谱中导出了相对积分强度，并给出了所用方法的示例。

  DOI：

  10.1016/0022-2852(89)90018-0
• 作为产物：
  描述：

  吗啡 在 氢氧化钾 作用下， 生成 甲胺
  参考文献：
  名称：

  Wertheim, Justus Liebigs Annalen der Chemie, 1850, vol. 73, p. 210

  摘要：

  DOI：
• 作为试剂：
  描述：

  4-氯苯甲醛 在 盐酸 、 氯化亚砜 、 potassium carbonate 、 溶剂黄146 、 甲胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  一系列新型三唑和2,4-噻唑烷二酮杂化酰胺衍生物的合成及生物学评价

  摘要：

  一系列具有通过连接体连接的三唑和噻唑烷核的杂化化合物已被合成并进行了广泛的研究。已经测试了目标化合物的各种合成方法。对所获得的化合物进行了病原真菌白色念珠菌、非白色念珠菌、多重耐药念珠菌、根霉、曲霉属菌株的微生物学评估。以及一些皮肤癣菌和其他酵母菌。目标化合物的最低 MIC 值在 0.003 µg/mL 至 0.5 µg/mL 之间，因此这些化合物不比商业唑类药物差或好几倍。酰基哌嗪接头的长度对抗真菌活性的影响有限。一些生物等排类似物在微生物分析中进行了测试，但结果证明其活性弱于先导物质。噻唑烷片段中具有对氯亚苄基取代基的化合物表现出最高的活性。分子模型用于预测合成分子的结合模式并合理化实验观察到的 SAR。与伏立康唑相比，前导化合物在抑制白色念珠菌酵母细胞形成芽管方面的效果高出两倍。观察到吡咯类药物外排泵 Pdr5 水平增加，但增加幅度低于唑类引起的水平。研究结果可用于进一步开发更强大、更安全的抗真菌药物。

  DOI：

  10.3390/ph17060723

文献信息

• Alkyl 1-Chloroalkyl Carbonates: Reagents for the Synthesis of Carbamates and Protection of Amino Groups
  作者：Gérard Barcelo、Jean-Pierre Senet、Gérard Sennyey、Jean Bensoam、Albert Loffet

  DOI：10.1055/s-1986-31724

  日期：——

  The synthesis of 1-chloroalkyl carbonates and their reaction with various type of amines are described. This reaction is useful for the synthesis of carbamate pesticides and for the protection of various amino groups, including amino acids.

  描述了1-氯代烷基碳酸酯的合成及其与各种类型胺的反应。这一反应对于合成氨基甲酸酯类农药和保护包括氨基酸在内的各种氨基团具有重要作用。
• BENZOTHIOPHENE INHIBITORS OF RHO KINASE
  申请人：Kahraman Mehmet

  公开号：US20080021026A1

  公开（公告）日：2008-01-24

  The present invention relates to compounds and methods which may be useful as inhibitors of Rho kinase for the treatment or prevention of disease.

  本发明涉及化合物和方法，这些化合物和方法可能作为Rho激酶的抑制剂在治疗或预防疾病方面有用。
• Enantioselective Transfer Hydrogenation of Aliphatic Ketones Catalyzed by Ruthenium Complexes Linked to the Secondary Face of β-Cyclodextrin
  作者：Alain Schlatter、Wolf-D. Woggon

  DOI：10.1002/adsc.200700558

  日期：2008.5.5

  Ruthenium-η-arene complexes attached to the secondary face of β-cyclodextrin catalyze the enantioselective reduction (ee up to 98%) of aliphatic and aromatic ketones in aqueous medium in the presence of sodium formate (HCOONa).

  在甲酸钠（HCOONa）存在下，附着在β-环糊精第二面上的钌-η-芳烃络合物催化水性介质中脂肪族和芳香族酮的对映选择性还原（ee高达98％）。
• Ammonia–dimethylchloramine system: Kinetic approach in an aqueous medium and comparison with the mechanism involving liquid ammonia
  作者：J. Stephan、V. Pasquet、M. Elkhatib、V. Goutelle、H. Delalu

  DOI：10.1002/kin.20312

  日期：2008.6

  medium. Dimethylchloramine prepared in a pure state undergoes dehydrohalogenation in an alkaline medium: the principal products formed are N-methylmethanimine, 1,3,5-trimethylhexahydrotriazine, formaldehyde, and methylamine. The kinetics of this reaction was studied by UV, GC, and HPLC as a function of temperature, initial concentrations of sodium hydroxide, and chlorinated derivative. The reaction is of

  在对液氨中的氨-二甲基氯胺系统进行了详尽的研究之后，比较该系统在液氨中的反应性与相同系统在水性介质中的反应性是很有趣的。以纯态制备的二甲基氯胺在碱性介质中进行脱卤化氢：形成的主要产物是 N-甲基甲亚胺、1,3,5-三甲基六氢三嗪、甲醛和甲胺。该反应的动力学通过 UV、GC 和 HPLC 作为温度、氢氧化钠初始浓度和氯化衍生物的函数进行了研究。该反应是二级反应，遵循 E2 机理（k1 = 4.2 × 10-5 M-1 s-1，ΔH○# = 82 kJ mol-1，ΔS○# = -59 J mol-1 K-1 ）。二甲基氯胺氧化不对称二甲基肼涉及两个连续的过程。第一步遵循关于卤胺和肼的一级定律，导致形成氨基氮烯中间体 (k2 = 150 × 10-5 M-1 s-1)。第二步对应于在 pH 13) 下将氨基氮烯转化为甲醛二甲腙。该反应遵循一阶定律 (k3 = 23.5 × 10-5 s-1)。二甲基氯胺-氨相互作用对应于
• Identification of Pyridine Synthase Recognition Sequences Allows a Modular Solid-Phase Route to Thiopeptide Variants
  作者：Walter J. Wever、Jonathan W. Bogart、Albert A. Bowers

  DOI：10.1021/jacs.6b05389

  日期：2016.10.19

  Bacillus cereus ATCC 14579. Through a series of truncations, we define a minimum recognition sequence (RS) that is necessary and sufficient for TclM activity. This RS can be readily synthesized and ligated to linear thiopeptide cores prepared via solid-phase peptide synthesis (SPPS), giving an efficient and modular route to thiopeptide variants. We exploit this strategy to define C-terminal core peptide requirements

  硫肽是结构复杂、具有生物活性的天然产物，来源于核糖体合成和翻译后修饰的肽。最近发现一组显着的酶通过正式的 [4 + 2] 环加成催化硫肽核心三噻唑基吡啶的形成。这些吡啶合酶通常在硫肽生物合成的后期作用以影响 N 末端前导肽的大环化和切割，使其成为制备新硫肽变体的潜在有用的生物催化剂。在这里，我们研究了蜡样芽孢杆菌 ATCC 14579 中硫西林生物合成对 TclM 的前导肽要求。通过一系列截断，我们定义了 TclM 活性所必需和充分的最小识别序列 (RS)。这种 RS 可以很容易地合成并连接到通过固相肽合成 (SPPS) 制备的线性硫肽核心，从而为硫肽变体提供高效和模块化的途径。我们利用这种策略来定义 C 末端核心肽的要求，并探索两种吡啶合酶 TclM 和 TbtD 的混杂性差异，最终检查它们获得新结构变体的能力。

表征谱图