替苯丙胺 | 4764-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 中文名称: 替苯丙胺
• 英文名称: MDA
• 英文别名: 3,4-methylenedioxyamphetamine；methylenedioxyamphetamine；1-(benzo[d][1,3]dioxol-5-yl)propan-2-amine；(±)-MDA；(R/S)-1-(3,4-methylenedioxyphenyl)-2-amino-propane；(+/-)-Tenamfetamine；Tenamphetamine；Tenamfetamine；1-(1,3-benzodioxol-5-yl)propan-2-amine
• CAS: 4764-17-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: NGBBVGZWCFBOGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

设计药物甲氧基安非他明（MDA）、R,S-甲氧基甲基安非他明（MDMA）、R,S-甲氧基乙基安非他明（MDE）、R, S-苯并二氧杂唑基丁胺（BDB）和R, S-N-甲基-苯并二氧杂唑基丁胺（MBDB）的一相和二相代谢物通过气相色谱-质谱（GC-MS）或液相色谱-质谱（LC-MS）在人类和大鼠的尿液和肝脏微粒体中进行了鉴定。可以假设出两个重叠的途径：（1）去甲基化随后通过儿茶酚-O-甲基转移酶（COMT）催化的甲基化以及/或葡萄糖醛酸化/硫酸化；（2）N-脱烷基化、脱氨，仅对于MDA、MDMA、MDE，氧化为相应的苯甲酸衍生物与甘氨酸结合。去甲基化主要由CYP2D1/6或CYP3A2/4催化，但也可以通过CYP独立机制进行。在人类中，MDMA和MBDB也可以通过CYP1A2去甲基化。N-脱甲基化主要由CYP1A2催化，N-脱乙基化由CYP3A2/4催化。...

The phase I and II metabolites of the designer drugs methylenedioxyamphetamine (MDA), R,S-methylenedioxymethamphetamine (MDMA), R,S-methylenedioxyethylamphetamine (MDE), R, S-benzodioxazolylbutanamine (BDB) and R, S-N-methyl-benzodioxazolylbutanamine (MBDB) were identified by gas chromatography-mass spectrometry (GC-MS) or liquid chromotography-mass spectrometry (LC-MS) in urine and liver microsomes of humans and rats. Two overlapping pathways could be postulated: (1) demethylenation followed by catechol-O-methyl-transferase (COMT) catalyzed methylation and/or glucuronidation/sulfatation; (2) N-dealkylation, deamination and only for MDA, MDMA, MDE oxidation to the corresponding benzoic acid derivatives conjugated with glycine. Demethylenation was mainly catalyzed by CYP2D1/6 or CYP3A2/4, but also by CYP independent mechanisms. In humans, MDMA and MBDB could also be demethylenated by CYP1A2. N-demethylation was mainly catalyzed by CYP1A2, N-deethylation by CYP3A2/4. ...

来源:Hazardous Substances Data Bank (HSDB)

代谢

MDA的两个主要代谢物，即alpha-甲基多巴胺（alpha-MeDA）和3-O-甲基-alpha-甲基多巴胺（3-O-Me-alpha-MeDA），被注射到大鼠的脑室内和脑实质中。此外，它们的先驱物质，即（alpha-MeDOPA和3-O-Me-alpha-MeDOPA）被单独和联合地系统给药。这些处理均未产生持久的大脑血清素（5-HT）耗竭。这些发现表明，MDA的任何一个主要代谢物都没有介导其对5-HT神经元的毒性作用，可能是由于一个次要代谢物负责，或者是其他机制参与其中。

The two major metabolites of (+/-)3,4-methylenedioxyamphetamine (MDA), alpha-methyldopamine (alpha-MeDA) and 3-O-methyl-alpha-methyldopamine (3-O-Me-alpha-MeDA), were administered to rats intracerebroventricularly and into brain parenchyma. In addition, their precursors, (alpha-MeDOPA and 3-O-Me-alpha-MeDOPA, respectively) were administered systemically, individually and in combination. None of these treatments produced a lasting depletion of brain serotonin (5-HT). These findings suggest that neither of MDA's major metabolites mediate its toxic effects on 5-HT neurons and that either a minor metabolite is responsible or that alternate mechanisms are involved.

来源:Hazardous Substances Data Bank (HSDB)

代谢

3,4-亚甲二氧基苯丙胺（MDA）和3,4-亚甲二氧基甲基苯丙胺（MDMA，摇头丸）是具有刺激和致幻作用的环取代苯丙胺衍生物。尽管有对中枢神经系统造成不可逆损害的警告，这些苯丙胺的娱乐使用，尤其是MDMA，仍然很普遍。MDA和MDMA主要是血清素神经毒素。因为（1）MDA或MDMA直接注射到大脑中不会产生神经毒性，（2）一些MDA和MDMA的主要代谢物通过脑室内给药（i.c.v.）不能复制它们的神经毒性，（3）α-甲基多巴胺（α-MeDA）和N-甲基-α-MeDA是MDA和MDMA的代谢物，（4）α-MeDA和N-甲基-α-MeDA容易被氧化成相应的邻醌，这些邻醌可以与谷胱甘肽（GSH）发生结合，（5）醌硫醚表现出多种毒理学活性，/研究者/开始了关于α-MeDA和N-甲基-α-MeDA的硫醚代谢物在MDA和MDMA神经毒性中潜在作用的研究。/这些/研究发现，硫醚结合物刺激了血清素、多巴胺和去甲肾上腺素的急性释放，并产生了与“血清素综合征”相一致的行为反应。将结合物直接注射到大鼠大脑中也会导致血清素（5-HT）浓度的长期降低、GFAP表达升高和微胶质细胞的激活。这些数据与α-MeDA和N-甲基-α-MeDA的硫醚代谢物有助于亲本苯丙胺的神经毒性的观点一致。

3,4-Methylenedioxyamphetamine (MDA) and 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) are ring-substituted amphetamine derivatives with stimulant and hallucinogenic properties. The recreational use of these amphetamines, especially MDMA, is prevalent despite warnings of irreversible damage to the central nervous system. MDA and MDMA are primarily serotonergic neurotoxicants. Because (1) neither MDA nor MDMA produces neurotoxicity when injected directly into brain, (2) intracerebroventricular (i.c.v.) administration of some major metabolites of MDA and MDMA fails to reproduce their neurotoxicity, (3) alpha-methyldopamine (alpha-MeDA) and N-methyl-alpha-MeDA are metabolites of both MDA and MDMA, (4) alpha-MeDA and N-methyl-alpha-MeDA are readily oxidized to the corresponding ortho-quinones, which can undergo conjugation with glutathione (GSH), and (5) quinone thioethers exhibit a variety of toxicologic activities, /the investigators/ initiated studies on the potential role of thioether metabolites of alpha-MeDA and N-methyl-alpha-MeDA in the neurotoxicity of MDA and MDMA. /These/ studies have revealed that the thioether conjugates stimulate the acute release of serotonin, dopamine, and norepinephrine and produce a behavioral response commensurate with the "serotonin syndrome." Direct injection of the conjugates into rat brain also produces long-term depletions in serotonin (5-HT) concentrations, elevations in GFAP expression, and activation of microglial cells. The data are consistent with the view that thioether metabolites of alpha-MeDA and N-methyl-alpha-MeDA contribute to the neurotoxicity of the parent amphetamines.

来源:Hazardous Substances Data Bank (HSDB)

代谢

3,4-亚甲二氧基苯丙胺（MDA）和3,4-甲基亚甲二氧基甲基苯丙胺（MDMA，摇头丸）是广泛滥用的苯丙胺衍生物，它们针对的是血清素系统。MDA和MDMA的血清素神经毒性似乎依赖于它们的系统性代谢。5-(谷胱甘肽-S-基)-α-甲基多巴胺[5-(GSyl)-α-MeDA]和2,5-双(谷胱甘肽-S-基)-α-甲基多巴胺[2,5-bis(GSyl)-α-MeDA]，MDA和MDMA的代谢物，也是选择性的血清素神经毒素，并且会产生与MDA和MDMA相似的行为和神经化学变化。5-(GSyl)-α-MeDA和2,5-bis(GSyl)-α-MeDA在抑制5-羟基色胺（血清素）进入瞬时转染了人血清素转运体（hSERT）的SK-N-MC细胞方面比MDA和MDMA更有效（K(i)分别为69、50、107和102微M）。此外，5-(GSyl)-α-MeDA和2,5-bis(GSyl)-α-MeDA同时刺激多巴胺（DA）进入表达hSERT的细胞，这种效果被氟西汀减弱，表明刺激的DA运输是hSERT依赖的。最后，5-(GSyl)-α-MeDA和2,5-bis(GSyl)-α-MeDA，以及较轻微的MDA和MDMA，在hSERT和转染了人多巴胺转运体的细胞中诱导了浓度和时间依赖性的活性氧种（ROS）增加。氟西汀减弱了hSERT表达细胞中ROS生成的增加。结果表明，MDA和MDMA的血清素神经毒性可能是由代谢依赖性的DA运输进入hSERT表达细胞以及由活性氧种生成的红氧活性儿茶酚硫醚代谢物和DA介导的。

3,4-Methylenedioxyamphetamine (MDA) and 3,4-methyl-enedioxymethamphetamine (MDMA, ecstasy) are widely abused amphetamine derivatives that target the serotonin system. The serotonergic neurotoxicity of MDA and MDMA seems dependent on their systemic metabolism. 5-(Glutathion-S-yl)-alpha-methyldopamine [5-(GSyl)-alpha-MeDA] and 2,5-bis(glutathion-S-yl)-alpha-methyldopamine [2,5-bis(GSyl)-alpha-MeDA], metabolites of MDA and MDMA, are also selective serotonergic neurotoxicants and produce behavioral and neurochemical changes similar to those seen with MDA and MDMA. 5-(GSyl)-alpha-MeDA and 2,5-bis(GSyl)-alpha-MeDA are more potent than MDA and MDMA (K(i) = 69, 50, 107, and 102 microM, respectively) at inhibiting 5-hy-droxytryptamine (serotonin) transport into SK-N-MC cells transiently transfected with the human serotonin transporter (hSERT). Moreover, 5-(GSyl)-alpha-MeDA and 2,5-bis(GSyl)-alpha-MeDA simultaneously stimulated dopamine (DA) transport into the hSERT-expressing cells, an effect attenuated by fluoxetine, indicating that stimulated DA transport was hSERT-dependent. Finally, 5-(GSyl)-alpha-MeDA and 2,5-bis(GSyl)-alpha-MeDA, and to a lesser extent MDA and MDMA, induced a concentration and time-dependent increase in reactive oxygen species (ROS) in both hSERT and human dopamine transporter-transfected cells. Fluoxetine attenuated the increase in ROS generation in hSERT-expressing cells. The results are consistent with the view that the serotonergic neurotoxicity of MDA and MDMA may be mediated by the metabolism-dependent stimulation of DA transport into hSERT-expressing cells and ROS generation by redox active catechol-thioether metabolites and DA.

来源:Hazardous Substances Data Bank (HSDB)

代谢

3,4-亚甲二氧基苯丙胺在狗和猴子尿液中的代谢物通过气液相色谱法分离，以其三氟乙酰化和/或正丁基醚衍生物的形式，并通过比较这些衍生物与合成化合物的色谱和质谱行为来鉴定。在狗和猴子尿液中鉴定出的代谢物包括α-甲基多巴胺、3-O-甲基-α-甲基多巴胺和3,4-二羟基苄基甲基酮。猴子尿液中还含有3,4-亚甲二氧基苄基甲基酮和3,4-亚甲二氧基苯甲酸，后者以葡萄糖醛酸苷和/或硫酸盐结合物的形式存在，而狗尿液中则含有3-甲氧基-4-羟基苯甲酸，以葡萄糖醛酸苷和硫酸盐以外的结合物形式存在。两种物种中的酚类代谢物以自由形式存在，并且作为葡萄糖醛酸苷和/或硫酸盐结合物。

Metabolites of 3,4-methylenedioxyamphetamine in the urine of dogs and monkeys were separated by gas-liquid chromatography as their trifluoroacetyl and/or n-butyl ether derivatives and identified by comparison of the chromatographic and mass spectrometric behavior of these derivatives with those of synthetic compounds. The metabolites identified in dog and monkey urine were alpha-methyldopamine, 3-O-methyl-alpha-methyldopamine, and 3,4-dihydroxybenzyl methyl ketone. The monkey urine also contained 3,4-methylenedioxybenzyl methyl ketone and 3,4-methylenedioxybenzoic acid present as a glucuronide and/or sulfate conjugate, whereas the dog urine had 3-methoxy-4-hydroxybenzoic acid present as a conjugate other than glucuronide and sulfate. The phenolic metabolites in both species were present free and as glucuronide and/or sulfate conjugates.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

MDA等设计型安非他命药物（例如，... MDA）... 作为狂欢药物已经获得了流行和臭名。... 人类使用/滥用这类药物已经与多种不良反应有关，包括威胁生命的血清素综合症、肝毒性、神经毒性和精神病理学。

Designer drugs of the amphetamine type (eg, ... MDA) ... have gained popularity and notoriety as rave drugs. ... A variety of adverse effects have been associated with the use/abuse of this class of drugs in humans, including a life-threatening serotonin syndrome, hepatotoxicity, neurotoxicity, and psychopathology.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

对隔离和聚集的小鼠的致死性分别确定了分级ip剂量的D-安非他命、DL-4-甲氧基安非他命（PMA）、DL-2,5-二甲氧基安非他命（DMA）、DL-2,5-二甲氧基-4-溴安非他命（DOB）、DL-2,5-二甲氧基-4-甲基安非他命（DOM）和DL-3,4-亚甲二氧基安非他命（MDA）。对安非他命及其衍生物的致死效果的拮抗作用进行了测试的药物有：氯丙嗪（2.0 mg/kg）、普萘洛尔（10 mg/kg）和苯氧苄胺（30 mg/kg）。氯丙嗪在隔离和聚集的小鼠中都能显著防止安非他命的致死性，而苯氧苄胺在隔离的小鼠中也能产生保护作用，但普萘洛尔无效。在使用这三种药物之前，PMA、DMA或DOB并未达到等效的保护程度。只有苯氧苄胺在隔离的小鼠中能防止DOM的致死性。苯氧苄胺和普萘洛尔在两种居住条件下都提供了对MDA的广泛保护。...

Lethality to both isolated and aggregated mice was determined for graded ip doses of d-amphetamine, dl-4-methoxyamphetamine (PMA), dl-2,5-dimethoxyamphetamine (DMA), dl-2,5-dimethoxy-4-bromoamphetamine (DOB), dl-2,5-dimethoxy-4-methylamphetamine (DOM) and dl-3,4-methylenedioxyamphetamine (MDA). Haloperidol (2.0 mg/kg), propranolol (10 mg/kg) and phenoxybenzamine (30 mg/kg) were tested for ability to antagonize the lethal effects of amphetamine and its derivatives. Considerable protection against amphetamine lethality was produced by haloperidol in both isolated and aggregated mice and by phenoxybenzamine in isolated mice, but propranolol was ineffective. An equivalent degree of protection was not achieved by use of any of the three agents before PMA, DMA or DOB. Protection against DOM was achieved only with phenoxybenzamine and only for isolated mice. Extensive protection against MDA was supplied by both phenoxybenzamine and propranolol for either condition of housing. ...

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

立即急救：确保已经进行了充分去污。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、气囊面罩装置或口袋面罩，按训练进行操作。如有必要，执行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者向前倾或将其置于左侧（如果可能，头部向下）以保持呼吸道畅通，防止吸入。保持患者安静，维持正常体温。寻求医疗帮助。/毒物A和B/

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

基本治疗：建立专利气道（如需要，使用口咽或鼻咽气道）。如有必要，进行吸痰。观察呼吸不足的迹象，如有需要，协助通气。通过非循环呼吸面罩以10至15升/分钟的速度给予氧气。监测肺水肿，如有必要，进行治疗……。监测休克，如有必要，进行治疗……。预防癫痫发作，如有必要，进行治疗……。对于眼睛污染，立即用水冲洗眼睛。在运输过程中，用0.9%的生理盐水（NS）连续冲洗每只眼睛……。不要使用催吐剂。对于摄入，如果患者能吞咽、有强烈的咳嗽反射且不流口水，则用水冲洗口腔，并给予5毫升/千克，最多200毫升的水进行稀释……。在去污后，用干性无菌敷料覆盖皮肤烧伤……。/毒物A和B/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 解毒与急救

高级治疗：对于昏迷、严重肺水肿或严重呼吸困难的病人，考虑进行口咽或鼻咽气管插管以控制气道。使用气囊面罩装置的正压通气技术可能有益。考虑使用药物治疗肺水肿……。对于严重的支气管痉挛，考虑给予β受体激动剂，如沙丁胺醇……。监测心率和必要时治疗心律失常……。开始静脉输注D5W/SRP：“保持开放”，最小流量/。如果出现低血容量的迹象，使用0.9%的生理盐水（NS）或乳酸钠林格氏液。对于伴有低血容量迹象的低血压，谨慎给予液体。注意液体过载的迹象……。用地西泮或劳拉西泮治疗癫痫……。使用丙美卡因氢氯化物协助眼部冲洗……。/毒物A和B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

这篇论文首次评估了在五起死亡案例中发现的甲氧基甲基苯丙胺（MDMA）和3,4-亚甲二氧基苯丙胺（MDA）的浓度，这些案例中既有死前又有死后的血液样本。入院时MDMA和MDA的浓度分别在0.55到4.33毫克/升和0到0.10毫克/升之间，分别对应死前血清/血浆。死后血液中MDMA和MDA的浓度分别在0.47到28.39毫克/升和0.02到1.33毫克/升之间。在所有5个案例中，死后浓度都高于相应的死前浓度，MDMA的死后/死前比率在1.1到6.6之间，MDA的比率在1.5到13.3之间。不同解剖部位的浓度也有所不同，中心部位（例如心脏）的浓度远高于周围部位（例如股骨）。总的来说，MDMA和MDA似乎表现出死后重新分布，死后标本中测得的浓度（即使是周围部位的）与接近或临终前的死前发现并不直接可比。

... This paper describes for the first time an evaluation of the concentrations of methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) found in five fatalities admitted to hospital where both antemortem and postmortem blood samples were available. Admission MDMA and MDA concentrations ranged between 0.55 and 4.33 mg/L and 0 and 0.10 mg/L, respectively, in antemortem serum/plasma. Postmortem blood MDMA and MDA concentrations ranged between 0.47 and 28.39 mg/L and 0.02 and 1.33 mg/L, respectively. Postmortem concentrations were higher than corresponding antemortem concentrations in all 5 cases with postmortem/antemortem ratios between 1.1 and 6.6 for MDMA and 1.5 and 13.3 for MDA. Differences in concentrations were also observed between anatomical sites, with central sites (e.g., heart) having much higher concentrations than peripheral sites (e.g., femoral). Overall, MDMA and MDA appear to exhibit postmortem redistribution and concentrations measured in postmortem specimens (even from peripheral sites) are not directly comparable with antemortem findings close to or prior to death.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

数据...在这里报告的数据包括20起死亡案例中的心脏血液、胃内容物、尿液和胆汁标本中的甲氧基甲基安非他明（MDMA）和甲氧基安非他明（MDA）的死后分布；这20例心脏血液中发现的其它药物；以及25例生前尿液和6例头发标本中的MDMA和MDA分布。在有限的头发标本（n=6）中观察到的MDA/MDMA浓度比是一致的，并且似乎高于在其他标本中发现的比值。与其他常见滥用药物（例如，可卡因和海洛因）相比，头发中的“药物/代谢物”浓度比（MDMA/MDA）与其他标本（如尿液和血液）得出的比值没有显著差异。这一观察结果与报告的可卡因/苯甲酰 ecgonine、四氢大麻酚/四氢大麻酸和MDMA/MDA的相对药物/代谢物结合率一致。

Data ... reported /here/ include postmortem distribution of methylenedioxymethamphetamine (MDMA) and methylenedioxyamphetamine (MDA) in heart blood, gastric content, urine, and bile specimens from 20 fatal cases; other drugs found in the heart blood from these 20 cases; and the distribution of MDMA and MDA in 25 antemortem urine and 6 hair specimens. The MDA/MDMA concentration ratio observed in a limited number of hair specimens (n=6) are consistent and appear to be higher than those found in other specimens. Compared to other commonly abused drugs (e.g., cocaine and heroin), the "drug/metabolite" concentration ratio (MDMA/MDA) in hair is not significantly different from the ratios derived from other specimens, such as urine and blood. This observation is consistent with the relative drug/metabolite incorporation rates reported for cocaine/benzoylecgonine, tetrahydrocannabinol/tetrahydrocannabinoic acid, and MDMA/MDA.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  替苯丙胺 在 吡啶 、 三氯氧磷 作用下， 反应 10.0h， 生成 1,3-Dimethyl-6,7-methylendioxy-3,4-dihydro-isochinolin
  参考文献：
  名称：

  Rastogi, Shri Niwas; Kansal, V. K.; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 3, p. 234 - 237

  摘要：

  DOI：
• 作为产物：
  描述：

  异黄樟素 在 甲酸 、 双氧水 、 丙酮 作用下， 生成 替苯丙胺
  参考文献：
  名称：

  Fujisawa; Deguchi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 977,979

  摘要：

  DOI：

文献信息

• [EN] IMIDAZOLIUM REAGENT FOR MASS SPECTROMETRY<br/>[FR] RÉACTIF D'IMIDAZOLIUM POUR SPECTROMÉTRIE DE MASSE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2021234004A1

  公开（公告）日：2021-11-25

  The present invention relates to compounds which are suitable to be used in mass spectrometry as well as methods of mass spectrometric determination of analyte molecules using said compounds.

  本发明涉及适用于质谱的化合物，以及利用该化合物进行分析物分子的质谱测定方法。
• Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine)
  作者：Ulrich Braun、Alexander T. Shulgin、Gisela Braun

  DOI：10.1002/jps.2600690220

  日期：1980.2

  The known central nervous system activity of 3,4-methylenedioxyphenylisopropylamine and its N-methyl homolog prompted the synthesis of a series of analogs with substituents on the nitrogen atom. Most of these analogs (R = alkyl, alkenyl, hydroxy, alkoxy, and alkoxyalkyl) were prepared by the reductive alkylation of 3,4-methylenedioxyphenylacetone with the appropriate amine and sodium cyanoborohydride

  3，4-亚甲基二氧基苯基异丙基胺及其N-甲基同系物的已知中枢神经系统活性促使合成一系列在氮原子上具有取代基的类似物。这些类似物的大多数（R =烷基，烯基，羟基，烷氧基和烷氧基烷基）是通过3,4-亚甲基二氧基苯基丙酮与适当的胺和氰基硼氢化钠进行还原性烷基化反应制备的。受阻异构体是间接合成的。在几种动物试验和人类受试者中对它们的药理活性的测量表明，中央活性随N取代基体积的增加而降低。
• [EN] AMPHETAMINE PRODRUGS<br/>[FR] PRO-MÉDICAMENTS À BASE D'AMPHÉTAMINES
  申请人：SHIRE AG

  公开号：WO2014002039A1

  公开（公告）日：2014-01-03

  The present invention relates to amphetamine prodrugs which provide colonic release of amphetamine.

  本发明涉及提供苯丙胺结肠释放的苯丙胺前药。
• AMPHETAMINE CONTROLLED RELEASE, PRODRUG, AND ABUSE-DETERRENT DOSAGE FORMS
  申请人：CHEMAPOTHECA, LLC

  公开号：US20180243241A1

  公开（公告）日：2018-08-30

  The invention also relates to pharmaceutical compositions comprising highly pure amphetamine and amphetamine-class compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds, and to methods of manufacturing, delivering, and using the amphetamine compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds.

  这项发明还涉及包含高纯度苯丙胺和苯丙胺类化合物的药物组合物，这些化合物是通过对手性和消旋苯丙胺衍生物进行立体特异性、区域选择性的杯酸盐加成反应与环氧乙烷磷酰胺化合物合成而得到的，并且涉及通过对手性和消旋苯丙胺衍生物进行立体特异性、区域选择性的杯酸盐加成反应与环氧乙烷磷酰胺化合物合成而得到的苯丙胺化合物的制造、输送和使用方法。
• [EN] AMPHETAMINE CONTROLLED RELEASE, PRODRUG, AND ABUSE DETERRENT DOSAGE FORMS<br/>[FR] LIBÉRATION CONTRÔLÉE DE L'AMPHÉTAMINE, PROMÉDICAMENT ET FORMES POSOLOGIQUES DISSUASIVES DU MÉSUSAGE
  申请人：CHEMAPOTHECA LLC

  公开号：WO2017147375A1

  公开（公告）日：2017-08-31

  The invention also relates to pharmaceutical compositions comprising highly pure amphetamine and amphetamine-class compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds, and to methods of manufacturing, delivering, and using the amphetamine compounds resulting from the synthesis of chiral and racemic amphetamine derivatives by stereospecific, regioselective cuprate addition reaction with aziridine phosphoramidate compounds.

  这项发明还涉及包含高纯度苯丙胺和苯丙胺类化合物的药物组合物，这些化合物是通过对手性和消旋苯丙胺衍生物进行立体特异性、区域选择性的杯酸盐加成反应与环氧乙烷磷酰胺化合物合成的，以及通过对手性和消旋苯丙胺衍生物进行立体特异性、区域选择性的杯酸盐加成反应与环氧乙烷磷酰胺化合物合成的苯丙胺化合物的制造、输送和使用方法。

表征谱图