N-羟基甲基苯丙胺 | 52271-36-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-羟基甲基苯丙胺
• 中文别名: 7H-吡唑并[4,3-g]苯并噻唑(8CI)
• 英文名称: methamphetamine hydroxylamine
• 英文别名: N-Hydroxy-N-Methylamphetamin；N-methyl-N-(1-phenylpropan-2-yl)hydroxylamine
• CAS: 52271-36-0
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: PCDVFYKROPOLBF-UHFFFAOYSA-N

物化性质

• 溶解度：
  氯仿（微溶）、DMSO（微溶）、乙醇（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-羟基甲基苯丙胺 在 potassium phosphate buffer 、 1,4-dihydronicotinamide adenine dinucleotide 、 human liver microsomes 作用下， 反应 0.5h， 生成 DL-甲基苯丙胺
  参考文献：
  名称：

  苯甲酰胺肟还原酶和人肝微粒体还原苯丙胺羟胺和其他脂肪族羟胺。

  摘要：

  为了还原强碱性官能团如am，胍和氨基amino的N-羟基化衍生物，已描述了对氧不敏感的肝微粒体系统，即苯甲酰胺肟还原酶。为了重建苯甲酰胺肟还原酶的完整活性，系统需要细胞色素b（5），NADH-细胞色素b（5）-还原酶和苯甲酰胺肟还原酶（一种细胞色素P450酶），该酶已从猪肝中纯化至同质。尚不清楚该酶系统是否还能够还原脂族羟胺。脂族胺的N-羟基化是众所周知的代谢过程。研究苯甲酰肟肟还原酶将脂族胺的N-羟基化代谢物还原回母体化合物的可能性是有意义的。总体，N-羟基化和还原将构成无效的代谢循环。作为医学上相关化合物的实例，研究了甲基苯丙胺，苯丙胺和N-甲基胺作为模型化合物的羟胺。通过新开发的HPLC方法分析了甲基苯丙胺和苯丙胺的形成。苯甲酰胺肟还原酶很容易将所有三种羟胺还原为其母体胺，甲基苯丙胺的还原速率分别为220.6 nmol min（-1）（mg蛋白质）（-1），5.25 nmol min（-1）（mg蛋白质）（-

  DOI：

  10.1021/tx000043t
• 作为产物：
  描述：

  DL-甲基苯丙胺 生成 N-羟基甲基苯丙胺
  参考文献：
  名称：

  Synthesis of N-alkyl-N-hydroxyamphetamines and related nitrones

  摘要：

  DOI：

  10.1016/0040-4020(73)80256-x

文献信息

• Identification of a nitrone as anin vitro metabolite ofN-methylamphetamine
  作者：R. T. Coutts、G. R. Jones、S.-F. Liu

  DOI：10.1002/bms.1200050609

  日期：1978.6

  chromatographic and gas chromatographic mass spectrometric characteristics determined to confirm that the metabolically formed nitrone was not N-(alpha-methylbenzeneethylidene) methylamine N-oxide. Two previously unreported metabolites of (+/-)-Nmethylamphetamine, N-hydroxyamphetamine and 1-hydroxy-1-phenyl-2-propanone, were isolated from rat in vitro experiments; the latter metabolite was not produced in vitro

  从（+/-）-N-甲基苯异丙胺与来自大鼠和兔子的强化肝匀浆中孵育，分离出相对不稳定的硝酮，α-甲基-（N-亚甲基）苯乙胺N-氧化物。直接通过气相色谱和气相色谱质谱法确认硝酮的鉴定，然后在甲基丙烯酸甲酯和丙烯酸乙酯的作用下将其转化为异恶唑烷加合物。由N-羟基苯丙胺和甲醛明确合成了真实的硝酮样品。还合成了异构体硝酮N-（α-甲基苯乙叉基）甲胺N-氧化物，并通过气相色谱和气相色谱质谱分析确定了代谢产物形成的硝酮不是N-（α-甲基苯乙叉基）甲胺N-氧化物。 。从大鼠体外实验中分离出两种以前未报告的（+/-）-Nmethylamphetamine代谢产物N-hydroxyamphetamine和1-hydroxy-1-phenyl-2-propanone；后者的代谢产物不是由兔肝匀浆体外产生的。
• METHODS AND COMPOSITIONS FOR THE TREATMENT OF VASCULAR DEPRESSION
  申请人：Krishnan Ranga

  公开号：US20080064709A1

  公开（公告）日：2008-03-13

  Methods and compositions are provided for treating vascular depression. The methods involve administering to a subject in need thereof a xanthine derivative in a therapeutically effective amount to treat vascular depression, particularly the xanthine derivatives pentoxifylline or propentofylline. The methods may further include administration of an additional therapeutic agent in combination with the xanthine derivative selected from the group consisting of a selective serotonin reuptake inhibitor (SSRI), a serotonin-norepinephrine reuptake inhibitor (SNRI), and a drug used in the treatment of cerebrovascular disease. Compositions of the invention include pharmaceutical compositions and kits for treating vascular depression in a subject in need thereof that include therapeutically effective amounts of a xanthine derivative and an additional therapeutic agent selected from the group consisting of an SSRI, an SNRI, and a drug used in the treatment of cerebrovascular disease.
• XANTHINE DERIVATIVES FOR THE TREATMENT OF VASCULAR DEPRESSION
  申请人：Krishnan Ranga

  公开号：US20090258860A1

  公开（公告）日：2009-10-15

  Methods and compositions are provided for treating vascular depression. The methods involve administering to a subject in need thereof a xanthine derivative in a therapeutically effective amount to treat vascular depression, particularly the xanthine derivatives pentoxifylline or propentofylline. The methods may further include administration of an additional therapeutic agent in combination with the xanthine derivative selected from the group consisting of a selective serotonin reuptake inhibitor (SSRI), a serotonin-norepinephrine reuptake inhibitor (SNRI), and a drug used in the treatment of cerebrovascular disease. Compositions of the invention include pharmaceutical compositions and kits for treating vascular depression in a subject in need thereof that include therapeutically effective amounts of a xanthine derivative and an additional therapeutic agent selected from the group consisting of an SSRI, an SNRI, and a drug used in the treatment of cerebrovascular disease.
• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF VASCULAR DEPRESSION<br/>[FR] MÉTHODES ET COMPOSITIONS DE TRAITEMENT DE LA DÉPRESSION VASCULAIRE.
  申请人：UNIV DUKE

  公开号：WO2008033754A2

  公开（公告）日：2008-03-20

  [EN] Methods and compositions are provided for treating vascular depression. The methods involve administering to a subject in need thereof a xanthine derivative in a therapeutically effective amount to treat vascular depression, particularly the xanthine derivatives pentoxifylline or propentofylline. The methods may further include administration of an additional therapeutic agent in combination with the xanthine derivative selected from the group consisting of a selective serotonin reuptake inhibitor (SSRI), a serotonin-norepinephrine reuptake inhibitor (SNRI), and a drug used in the treatment of cerebrovascular disease. Compositions of the invention include pharmaceutical compositions and kits for treating vascular depression in a subject in need thereof that include therapeutically effective amounts of a xanthine derivative and an additional therapeutic agent selected from the group consisting of an SSRI, an SNRI, and a drug used in the treatment of cerebrovascular disease.
  [FR] L'invention porte sur des méthodes et compositions de traitement de la dépression vasculaire. Les méthodes consistent à administrer à un patient le nécessitant une dose à effet thérapeutique de dérivé de xantine et en particulier ses dérivés pentoxifylline ou propentofylline. Les méthodes peuvent également consister à administrer un agent thérapeutique additionnel sélectionné parmi un inhibiteur sélectif du recaptage de la sérotonine (SSRI), un inhibiteur du recaptage de la sérotonine-norépinéphrine (SNRI), et un médicament de traitement des maladies cérébrovasculaires. Les compositions de l'invention comportent des préparations pharmaceutiques et trousses contenant un dérivé de la xantine et un agent thérapeutique additionnel sélectionné parmi un SSRI, un SNRI), et un médicament de traitement des maladies cérébrovasculaires.
• Reduction of Amphetamine Hydroxylamine and Other Aliphatic Hydroxylamines by Benzamidoxime Reductase and Human Liver Microsomes
  作者：Bernd Clement、Detlef Behrens、Wenke Möller、John R. Cashman

  DOI：10.1021/tx000043t

  日期：2000.10.1

  benzamidoxime reductase, has been described. To reconstitute the complete activity of the benzamidoxime reductase, the system required cytochrome b(5), NADH-cytochrome b(5)-reductase, and the benzamidoxime reductase, a cytochrome P450 enzyme, which has been purified to homogeneity from pig liver. It was not known if this enzyme system was also capable of reducing aliphatic hydroxylamines. The N-hydroxylation

  为了还原强碱性官能团如am，胍和氨基amino的N-羟基化衍生物，已描述了对氧不敏感的肝微粒体系统，即苯甲酰胺肟还原酶。为了重建苯甲酰胺肟还原酶的完整活性，系统需要细胞色素b（5），NADH-细胞色素b（5）-还原酶和苯甲酰胺肟还原酶（一种细胞色素P450酶），该酶已从猪肝中纯化至同质。尚不清楚该酶系统是否还能够还原脂族羟胺。脂族胺的N-羟基化是众所周知的代谢过程。研究苯甲酰肟肟还原酶将脂族胺的N-羟基化代谢物还原回母体化合物的可能性是有意义的。总体，N-羟基化和还原将构成无效的代谢循环。作为医学上相关化合物的实例，研究了甲基苯丙胺，苯丙胺和N-甲基胺作为模型化合物的羟胺。通过新开发的HPLC方法分析了甲基苯丙胺和苯丙胺的形成。苯甲酰胺肟还原酶很容易将所有三种羟胺还原为其母体胺，甲基苯丙胺的还原速率分别为220.6 nmol min（-1）（mg蛋白质）（-1），5.25 nmol min（-1）（mg蛋白质）（-