(+)-p-Hydroxymethamphetamine | 85482-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-p-Hydroxymethamphetamine
• 英文别名: 4-hydroxyD-methamphetamine；4-hydroxymethamphetamine；4-((S)-2-Methylamino-propyl)-phenol；4-[(2S)-2-(methylamino)propyl]phenol
• CAS: 85482-67-3
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: SBUQZKJEOOQSBV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

4-羟基甲基安非他明是甲基安非他明的一个已知人体代谢物。

4-Hydroxymethamphetamine is a known human metabolite of Metamphetamine.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 作用下， 生成 (+)-p-Hydroxymethamphetamine
  参考文献：
  名称：

  DE683693

  摘要：

  公开号：

文献信息

• DE767161
  申请人：——

  公开号：——

  公开（公告）日：——
• METHODS OF TREATMENT, DIAGNOSIS AND MONITORING FOR METHAMPHETAMINE TOXICITY WHICH TARGET CERAMIDE METABOLIC PATHWAYS AND CELLULAR SENESCENCE
  申请人：The Regents of the University of California

  公开号：US20150148387A1

  公开（公告）日：2015-05-28

  Methamphetamine is a highly addictive psychostimulant that causes profound damage to the brain and other body organs. Post mortem studies of human tissues have linked the use of this drug to diseases associated with aging, such as coronary atherosclerosis, but the molecular mechanism underlying these findings remains unknown. We report now that methamphetamine accelerates cellular senescence in vitro and activates transcription of genes involved in cell-cycle control and inflammation in vivo by stimulating production of the sphingolipid messenger ceramide. This pathogenic cascade is triggered by reactive oxygen species, generated through methamphetamine metabolism via cytochrome P 450 -2D6, which recruit nuclear factor (NF)-KB to induce expression of enzymes in the de novo pathway of ceramide biosynthesis. Inhibitors of ceramide formation prevent methamphetamine-induced senescence and attenuate systemic inflammation and health deterioration in rats self-administering the drug. The results support therapeutic approaches to reduce the adverse consequences of methamphetamine abuse and improve effectiveness of treatments.
• [EN] METHODS OF TREATMENT, DIAGNOSIS AND MONITORING FOR METHAMPHETAMINE TOXICITY WHICH TARGET CERAMIDE METABOLIC PATHWAYS AND CELLULAR SENESCENCE<br/>[FR] PROCÉDÉS DE TRAITEMENT, DE DIAGNOSTIC ET DE SURVEILLANCE DE LA TOXICITÉ DE LA MÉTHAMPHÉTAMINE QUI CIBLENT DES VOIES MÉTABOLIQUES DES CÉRAMIDES ET LA SÉNESCENCE CELLULAIRE
  申请人：UNIV CALIFORNIA

  公开号：WO2013149250A1

  公开（公告）日：2013-10-03

  Methamphetamine is a highly addictive psychostimulant that causes profound damage to the brain and other body organs. Post mortem studies of human tissues have linked the use of this drug to diseases associated with aging, such as coronary atherosclerosis, but the molecular mechanism underlying these findings remains unknown. We report now that methamphetamine accelerates cellular senescence in vitro and activates transcription of genes involved in cell-cycle control and inflammation in vivo by stimulating production of the sphingolipid messenger ceramide. This pathogenic cascade is triggered by reactive oxygen species, generated through methamphetamine metabolism via cytochrome Pas0-2D6, which recruit nuclear factor (NF)-KB to induce expression of enzymes in the de novo pathway of ceramide biosynthesis. Inhibitors of ceramide formation prevent methamphetamine-induced senescence and attenuate systemic inflammation and health deterioration in rats self- administering the drug. The results support therapeutic approaches to reduce the adverse consequences of methamphetamine abuse and improve effectiveness of treatments.