(R,S)-3-(2-碘-5-硝基苯甲酰)-1-(1-甲基-2-哌啶甲基)-1H-吲哚

David Zhang 2024-11-26

(R,S)-3-(2-碘-5-硝基苯甲酰)-1-(1-甲基-2-哌啶甲基)-1H-吲哚

常用名：(R,S)-3-(2-碘-5-硝基苯甲酰)-1-(1-甲基-2-哌啶甲基)-1H-吲哚

CAS号：444912-48-5

英文名：AM1241

中文别名：N/A

名称

中文名：(2-碘-5-硝基苯基)(1-((1-甲基哌啶-2-基)甲基)-1H-吲哚-3-基)甲酮
英文名：am-1241
英文别名：更多

生物活性

描述：AM1241是一种有效的,典型的[2],选择性的CB2receptor激动剂,对小鼠脾脏的CB2受体的Ki值为3.4nM,对大鼠大脑CB1受体的Ki值为280nM,在啮齿动物组织中,对CB2受体的选择性是对CB1受体的280倍[1]。AM1241能够缓解偏头痛、中风和神经性头痛,对帕金森病也有效果[2]。AM1241可以抑制氧化损伤,通过Akt和Erk1/2的磷酸化激活STAT3[3]。
相关类别：信号通路>>G蛋白偶联受体/G蛋白>>大麻素受体研究领域>>神经疾病
靶点：

Ki:3.4nM(MousespleenCB2receptor),280nM(RatbrainCB1receptor)[1]

体外研究：AM1241是一种有效的选择性CB2受体激动剂,在小鼠脾脏中Ki为3.4nM,大鼠脑中CB1受体的Ki为280nM,对啮齿动物组织中CB2受体的选择性为82倍[1]。AM1241降低氧化应激水平,增强旁分泌生长因子的产生,降低TGF-β1和PDGF水平,通过Akt和Erk1/2的磷酸化激活Stat3[3]。
体内研究：AM1241(0.1-3mg/kg,ip)剂量依赖性地抑制大鼠的感觉超敏反应。在缺乏CB1受体的小鼠中,AM1241分别抑制1mg/kg和3mg/kg的触觉超敏反应和热敏感[1]。AM1241(0.75,1.5,3,6,12mg/kg,ip)减轻MPTP诱导的帕金森病并促进PD小鼠多巴胺能(DA)神经元的再生[2]。
参考文献：

[1].IbrahimMM,etal.ActivationofCB2cannabinoidreceptorsbyAM1241inhibitsexperimentalneuropathicpain:paininhibitionbyreceptorsnotpresentintheCNS.ProcNatlAcadSciUSA.2003Sep2;100(18):10529-33.

[2].ShiJ,etal.AM1241alleviatesMPTP-inducedParkinson’sdiseaseandpromotestheregenerationofDAneuronsinPDmice.Oncotarget.2017Jun29;8(40):67837-67850.

[3].HanD,etal.ActivationofcannabinoidreceptortypeIIbyAM1241protectsadipose-derivedmesenchymalstemcellsfromoxidativedamageandenhancestheirtherapeuticefficacyinmyocardialinfarctionmiceviaStat3activation.Oncotarget.2017May4;8(39):64853-64866.

物理化学性质

密度：1.3±0.1g/cm3
沸点：630.7±55.0°Cat760mmHg
分子式：C22H22IN3O3
分子量：503.33
闪点：335.2±31.5°C
PSA：71.06000
LogP：3.41
外观性状：yellow
蒸汽压：0.0±1.8mmHgat25°C
折射率：1.693
储存条件：-20℃
水溶解性：DMSO:~18mg/mLat60°C

安全信息

符号：
GHS07,GHS08
信号词：Danger
危害声明：H315-H319-H334-H335
警示性声明：P261-P305+P351+P338-P342+P311
个人防护装备：dustmasktypeN95(US);Eyeshields;Faceshields;Gloves
危害码(欧洲)：Xn
风险声明(欧洲)：36/37/38-42/43
安全声明(欧洲)：22-26-36/37-45
危险品运输编码：NONHforallmodesoftransport

文献6

更多文献：Self-medicationofacannabinoidCB2agonistinananimalmodelofneuropathicpain.

Pain152,1976-87,(2011)

Drugself-administrationmethodswereusedtotestthehypothesisthatratswouldself-medicatewithacannabinoidCB(2)agonisttoattenuateaneuropathicpainstate.Self-medicationoftheCB(2)ago…

：
：ActivationofCB2cannabinoidreceptorsbyAM1241inhibitsexperimentalneuropathicpain:paininhibitionbyreceptorsnotpresentintheCNS.

Proc.Natl.Acad.Sci.U.S.A.100,10529-10533,(2003)

WedesignedAM1241,aselectiveCB2cannabinoidreceptoragonist,andusedittotestthehypothesisthatCB2receptoractivationwouldreversethesensoryhypersensitivityobservedinneuropathicpai…

：
：CentralandperipheralsitesofactionforCB₂receptormediatedanalgesicactivityinchronicinflammatoryandneuropathicpainmodelsinrats.

Br.J.Pharmacol.162,428-40,(2011)

CannabinoidCB₂receptoractivationbyselectiveagonistshasbeenshowntoproduceanalgesiceffectsinpreclinicalmodelsofinflammatoryandneuropathicpain.However,mechanismsunderlyingCB₂-med…

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英文别名

：(2-iodo-5-nitrophenyl){1-[(1-methylpiperidin-2-yl)methyl]-1H-indol-3-yl}methanone
：Dacinostat
：LAQ-824
：(2-Iodo-5-nitrophenyl){1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl}methanone
：(E)-N-hydroxy-3-[4-[[2-hydroxyethyl-[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]prop-2-enamide
：UNII-V10P524501
：(2-Iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-Indol-3-yl)methanone
：2-Propenamide,N-hydroxy-3-[4-[[(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino]methyl]phenyl]-,(2E)-
：Methanone,(2-iodo-5-nitrophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]-
：(R,S)-3-(2-Iodo-5-nitrobenzoyl)-1-(1-methyl-2-piperidinylmethyl)-1H-indole
：(2E)-N-Hydroxy-3-[4-({(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylamide
：(2E)-N-hydroxy-3-[4-({(2-hydroxyethyl)[2-(1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enamide
：NVP-LAQ824
：UNII:DLM851L3RD
：S1095_Selleck
：AM1241