para-iodobenzylguanidine | 14629-42-6

• 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: para-iodobenzylguanidine
• 英文别名: 4-Iodobenzylguanidine；2-[(4-iodophenyl)methyl]guanidine
• CAS: 14629-42-6
• 化学式: C₈H₁₀IN₃
• 分子量: 275.092
• InChiKey: LZZMAYUQAQMFPR-UHFFFAOYSA-N

物化性质

• 沸点：
  330.7±44.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氰胺 、 4-碘苄胺盐酸盐 反应 4.0h， 生成 para-iodobenzylguanidine
  参考文献：
  名称：

  Adrenal medulla imaging agents: a structure-distribution relationship study of radiolabeled aralkylguanidines

  摘要：

  Fourteen 125I-labeled aralkylguanidines were synthesized and evaluated as potential imaging agents for the adrenal medullae and tumors of adrenomedullary origin. These guanidines are radiotracer analogues of guanethidine, an antihypertensive agent thought to mediate neuron blockade by uptake into adrenergic nerves. Dog adrenal medullae were used as a model to test radiotracer affinity for catecholamine storage tissue. Tissue distribution studies revealed that a number of radioiodinated guanidines showed pronounced localization in the adrenal medullae following intravenous injection, in certain cases exceeding that of either (-)-[3H]norepinephrine or [14C]guanethidine. (m-[125I]Iodobenzyl)guanidine (m-IBG, 2b) gave the best combination of high concentration and selectivity. The low adrenomedullary affinity observed with [14C]guanidine and m-[125I]iodobenzylamine demonstrates the uniqueness of the aralkylguanidine structure. Preliminary evidence suggests that 2b is a storage analogue of norepinephrine. [125I]2a is now being used clinically in imaging and radiotherapy of catecholamine tumors, such as pheochromocytoma.

  DOI：

  10.1021/jm00368a008

文献信息

• COMPOSITIONS, METHODS, AND SYSTEMS FOR THE SYNTHESIS AND USE OF IMAGING AGENTS
  申请人：Lantheus Medical Imaging, Inc.

  公开号：EP3567029A1

  公开（公告）日：2019-11-13

  The present invention relates to systems, compositions, and methods for the synthesis and use of imaging agents, or precursors thereof. An imaging agent precursor may be converted to an imaging agent using the methods described herein. In some cases, the imaging agent is enriched in 18F. In some cases, an imaging agent may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs. In some embodiments, methods and compositions for assessing perfusion and innervation mismatch in a portion of a subject are provided.

  本发明涉及合成和使用成像剂或其前体的系统、组合物和方法。成像剂前体可通过本文所述方法转化为成像剂。在某些情况下，成像剂富含 18F。在某些情况下，成像剂可用于成像受试者感兴趣的区域，包括但不限于心脏、心血管系统、心脏血管、大脑和其他器官。在一些实施方案中，提供了用于评估受试者部分灌注和神经支配失配的方法和组合物。
• Sympathetic Nervous System Blocking Agents. III. Derivatives of Benzylguanidine^1-3
  作者：James H. Short、Thomas D. Darby

  DOI：10.1021/jm00317a017

  日期：1967.9
• US9550000B2
  申请人：——

  公开号：US9550000B2

  公开（公告）日：2017-01-24
• Adrenal medulla imaging agents: a structure-distribution relationship study of radiolabeled aralkylguanidines
  作者：Donald M. Wieland、Thomas J. Mangner、Muthiah N. Inbasekaran、Lawrence E. Brown、Jiann Long Wu

  DOI：10.1021/jm00368a008

  日期：1984.2

  Fourteen 125I-labeled aralkylguanidines were synthesized and evaluated as potential imaging agents for the adrenal medullae and tumors of adrenomedullary origin. These guanidines are radiotracer analogues of guanethidine, an antihypertensive agent thought to mediate neuron blockade by uptake into adrenergic nerves. Dog adrenal medullae were used as a model to test radiotracer affinity for catecholamine storage tissue. Tissue distribution studies revealed that a number of radioiodinated guanidines showed pronounced localization in the adrenal medullae following intravenous injection, in certain cases exceeding that of either (-)-[3H]norepinephrine or [14C]guanethidine. (m-[125I]Iodobenzyl)guanidine (m-IBG, 2b) gave the best combination of high concentration and selectivity. The low adrenomedullary affinity observed with [14C]guanidine and m-[125I]iodobenzylamine demonstrates the uniqueness of the aralkylguanidine structure. Preliminary evidence suggests that 2b is a storage analogue of norepinephrine. [125I]2a is now being used clinically in imaging and radiotherapy of catecholamine tumors, such as pheochromocytoma.