• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

反式-2-(2,5-二甲氧基-4-碘苯基)环丙胺和反式-2-(2,5-二甲氧基-4-溴苯基)环丙胺是 5-HT(2)受体家族的强效激动剂。

trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT(2) receptor family.

机构信息

Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, IN 47907, USA.

出版信息

Beilstein J Org Chem. 2012;8:1705-9. doi: 10.3762/bjoc.8.194. Epub 2012 Oct 8.

DOI:10.3762/bjoc.8.194
PMID:23209503
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3511003/
Abstract

A strategy to replace the ethylamine side chain of 2,5-dimethoxy-4-iodoamphetamine (DOI, 1a), and 2,5-dimethoxy-4-bromoamphetamine (DOB, 1b) with a cyclopropylamine moiety was successful in leading to compounds with high affinity at the 5-HT(2) family of receptors; and the more potent stereoisomer of the cyclopropane analogues had the expected (-)-(1R,2S)-configuration. Screening for affinity at various serotonin receptor subtypes, however, revealed that the cyclopropane congeners also had increased affinity at several sites in addition to the 5-HT(2A) and 5-HT(2B) receptors. Therefore, at appropriate doses - although (-)-4 and (-)-5 may be useful as tools to probe 5-HT(2) receptor function - one would need to be mindful that their selectivity for 5-HT(2A) receptors is somewhat less than for DOI itself.

摘要

用环丙胺取代 2,5-二甲氧基-4-碘苯丙胺（DOI，1a）和 2,5-二甲氧基-4-溴苯丙胺（DOB，1b）中的乙胺侧链的策略是成功的，导致了对 5-HT（2）受体家族具有高亲和力的化合物；并且环丙烷类似物的更强立体异构体具有预期的（-）-（1R，2S）-构型。然而，在各种 5-羟色胺受体亚型上进行亲和力筛选时，发现除了 5-HT（2A）和 5-HT（2B）受体之外，环丙烷同系物在几个部位也具有更高的亲和力。因此，在适当的剂量下——尽管（-）-4 和（-）-5 可能可用作探测 5-HT（2）受体功能的工具——人们需要注意，它们对 5-HT（2A）受体的选择性略低于 DOI 本身。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/4b60ddaabf8a/Beilstein_J_Org_Chem-08-1705-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/1a9e885b3ad9/Beilstein_J_Org_Chem-08-1705-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/2b128729e8b8/Beilstein_J_Org_Chem-08-1705-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/e933eb5f3f44/Beilstein_J_Org_Chem-08-1705-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/4b60ddaabf8a/Beilstein_J_Org_Chem-08-1705-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/1a9e885b3ad9/Beilstein_J_Org_Chem-08-1705-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/2b128729e8b8/Beilstein_J_Org_Chem-08-1705-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/e933eb5f3f44/Beilstein_J_Org_Chem-08-1705-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/17ff/3511003/4b60ddaabf8a/Beilstein_J_Org_Chem-08-1705-g005.jpg

相似文献

1
trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT(2) receptor family.反式-2-(2,5-二甲氧基-4-碘苯基)环丙胺和反式-2-(2,5-二甲氧基-4-溴苯基)环丙胺是 5-HT(2)受体家族的强效激动剂。
Beilstein J Org Chem. 2012;8:1705-9. doi: 10.3762/bjoc.8.194. Epub 2012 Oct 8.
2
Interaction of 5-HT2A and 5-HT2C receptors in R(-)-2,5-dimethoxy-4-iodoamphetamine-elicited head twitch behavior in mice.5-HT2A 和 5-HT2C 受体在 R(-)-2,5-二甲氧基-4-碘苯丙胺诱发的小鼠头部抽动行为中的相互作用。
J Pharmacol Exp Ther. 2010 Dec;335(3):728-34. doi: 10.1124/jpet.110.172247. Epub 2010 Sep 21.
3
(1R, 3S)-(-)-trans-PAT: a novel full-efficacy serotonin 5-HT2C receptor agonist with 5-HT2A and 5-HT2B receptor inverse agonist/antagonist activity.(1R, 3S)-(-)-反式-PAT：一种新型的具有5-HT2A和5-HT2B受体反向激动剂/拮抗剂活性的全效血清素5-HT2C受体激动剂。
Eur J Pharmacol. 2009 Aug 1;615(1-3):1-9. doi: 10.1016/j.ejphar.2009.04.035. Epub 2009 May 3.
4
Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives.一系列反式-2-(吲哚-3-基)环丙胺衍生物的合成及其对血清素受体的亲和力
J Med Chem. 1998 Dec 3;41(25):4995-5001. doi: 10.1021/jm980318q.
5
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.
J Med Chem. 2004 Nov 18;47(24):6034-41. doi: 10.1021/jm040082s.
6
5-HT(2A) and 5-HT(2C) receptors exert opposing effects on locomotor activity in mice.5-羟色胺（2A）和5-羟色胺（2C）受体对小鼠的运动活动产生相反的影响。
Neuropsychopharmacology. 2009 Jul;34(8):1958-67. doi: 10.1038/npp.2009.29. Epub 2009 Mar 25.
7
LSD and the phenethylamine hallucinogen DOI are potent partial agonists at 5-HT2A receptors on interneurons in rat piriform cortex.麦角酸二乙酰胺（LSD）和苯乙胺类致幻剂DOI是大鼠梨状皮质中间神经元5-HT2A受体的强效部分激动剂。
J Pharmacol Exp Ther. 1996 Sep;278(3):1373-82.
8
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.5-羟色胺（5-HT）2A、2B和2C受体激动剂放射性配体结合位点的药理学特性
Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23. doi: 10.1007/s00210-004-0951-4. Epub 2004 Jul 30.
9
LSD and DOB: interaction with 5-HT2A receptors to inhibit NMDA receptor-mediated transmission in the rat prefrontal cortex.麦角酸二乙酰胺（LSD）和4-溴-2,5-二甲氧基苯乙胺（DOB）：与5-羟色胺2A（5-HT2A）受体相互作用以抑制大鼠前额叶皮质中N-甲基-D-天冬氨酸（NMDA）受体介导的神经传递。
Eur J Neurosci. 1999 Sep;11(9):3064-72. doi: 10.1046/j.1460-9568.1999.00726.x.
10
Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists.苯乙胺类血清素2A受体激动剂中2,5-二甲氧基结构单元的研究。
ACS Chem Neurosci. 2020 May 6;11(9):1238-1244. doi: 10.1021/acschemneuro.0c00129. Epub 2020 Apr 13.

引用本文的文献

1
Unravelling the target landscape of tranylcypromines for new drug discovery.解析反苯环丙胺的靶点格局以用于新药研发。
Acta Pharm Sin B. 2025 Jun;15(6):2985-3007. doi: 10.1016/j.apsb.2025.04.012. Epub 2025 Apr 14.
2
Discovery and Structure-Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT Receptor Agonists.发现并研究 2,5-二甲氧基苯哌啶类化合物作为选择性血清素 5-HT 受体激动剂的结构-活性关系。
J Med Chem. 2024 May 9;67(9):7224-7244. doi: 10.1021/acs.jmedchem.4c00082. Epub 2024 Apr 22.
3
DARK Classics in Chemical Neuroscience: NBOMes.

本文引用的文献

1
Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives.一系列反式-2-(吲哚-3-基)环丙胺衍生物的合成及其对血清素受体的亲和力
J Med Chem. 1998 Dec 3;41(25):4995-5001. doi: 10.1021/jm980318q.
2
Asymmetric synthesis of psychotomimetic phenylisopropylamines.拟精神病苯基异丙胺的不对称合成。
J Med Chem. 1973 May;16(5):480-3. doi: 10.1021/jm00263a013.
3
Binding to the serotonin 5-HT2 receptor by the enantiomers of 125I-DOI.
Neuropharmacology. 1987 Dec;26(12):1803-6. doi: 10.1016/0028-3908(87)90138-9.
化学神经科学中的黑暗经典：N-苯甲酰基-N-取代色胺类物质（NBOMes）
ACS Chem Neurosci. 2020 Dec 2;11(23):3860-3869. doi: 10.1021/acschemneuro.9b00528. Epub 2019 Nov 12.
4
Effects of dopaminergic and serotonergic compounds in rats trained to discriminate a high and a low training dose of the synthetic cathinone mephedrone.在训练大鼠区分高剂量和低剂量合成卡西酮甲卡西酮的过程中，多巴胺能和血清素能化合物的作用。
Psychopharmacology (Berl). 2019 Mar;236(3):1015-1029. doi: 10.1007/s00213-019-05241-z. Epub 2019 Apr 13.
5
In vivo evaluation of [F]FECIMBI-36, an agonist 5-HT receptor PET radioligand in nonhuman primate.[F]FECIMBI-36（一种5-羟色胺受体PET放射性配体激动剂）在非人灵长类动物体内的评估。
Bioorg Med Chem Lett. 2017 Jan 1;27(1):21-23. doi: 10.1016/j.bmcl.2016.11.043. Epub 2016 Nov 16.
6
Effect of 5-HT2A and 5-HT2C receptors on temporal discrimination by mice.5-羟色胺2A和5-羟色胺2C受体对小鼠时间辨别能力的影响。
Neuropharmacology. 2016 Aug;107:364-375. doi: 10.1016/j.neuropharm.2016.03.038. Epub 2016 Mar 25.
4
[125I]-2-(2,5-dimethoxy-4-iodophenyl)aminoethane ([125I]-2C-I) as a label for the 5-HT2 receptor in rat frontal cortex.
Pharmacol Biochem Behav. 1990 Jan;35(1):211-7. doi: 10.1016/0091-3057(90)90228-a.
5
LSD and phenethylamine hallucinogens: new structural analogy and implications for receptor geometry.麦角酸二乙胺（LSD）和苯乙胺类致幻剂：新的结构类比及其对受体几何形状的影响
Life Sci. 1978 Jun 26;22(24):2165-70. doi: 10.1016/0024-3205(78)90567-2.
6
Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue.强效致幻剂类似物反式-2-(2,5-二甲氧基-4-甲基苯基)环丙胺的拆分及绝对构型
J Med Chem. 1979 Apr;22(4):458-60. doi: 10.1021/jm00190a021.