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Merck
CN

U103

U-69593

selective κ opioid receptor agonist, solid

别名:

(+)-(5α,7α,8β)-N-甲基-N-[7-(1-吡咯烷基)-1-氧杂螺[4,5]癸-8-基]苯乙酰胺, U69593

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关于此项目

经验公式（希尔记法）:
C22H32N2O2
化学文摘社编号:
96744-75-1
分子量:
356.50
UNSPSC Code:
12352200
PubChem Substance ID:
24278769
NACRES:
NA.77
MDL number:
MFCD05664586

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产品名称

U-69593, solid

SMILES string

CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)Cc4ccccc4

InChI

1S/C22H32N2O2/c1-23(21(25)16-18-8-3-2-4-9-18)19-10-12-22(11-7-15-26-22)17-20(19)24-13-5-6-14-24/h2-4,8-9,19-20H,5-7,10-17H2,1H3/t19-,20-,22-/m0/s1

InChI key

PGZRDDYTKFZSFR-ONTIZHBOSA-N

form

solid

optical activity

[α]/D +7.8°, c = 0.825 in methanol(lit.)

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 10 mg/mL
0.1 M HCl: >40 mg/mL
ethanol: >40 mg/mL
0.1 M NaOH: insoluble
H2O: insoluble

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... OPRD1(4985), OPRK1(4986), OPRM1(4988)
mouse ... Oprk1(18387)
rat ... Oprd1(24613), Oprk1(29335), Oprm1(25601)

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相关类别

Biochem/physiol Actions

U-69593是一种选择性κ阿片受体激动剂。已知U-69593可通过使多巴胺的基础溢流正常化来抑制中肢多巴胺神经元中的可卡因敏化。

Features and Benefits

《受体分类和信号转导》手册的 阿片类药物受体页有该化合物的介绍。想要浏览手册的其他页面， 请单击此处。

Preparation Note

U-69593可溶于45% (w/v) 2-羟丙基-环糊精水溶液（10 mg/ml）、0.1 M HCl（>40 mg/ml）以及乙醇（>40 mg/ml）。然而，它不溶于0.1 M NaOH和水。

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000382428
0000382428
0000102364
0000073185
0000030456

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T Nakagawa et al.
Japanese journal of pharmacology, 81(4), 353-361 (2000-02-11)
Chronic and/or sustained opioid treatment has been shown to result in development of sensitization of the adenylyl cyclase (AC) system or cAMP overshoot. In this study, we investigated the molecular mechanism responsible for sensitization of the AC system using CHO
Karl J Iremonger et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 29(22), 7349-7358 (2009-06-06)
Opioid signaling in the CNS is critical for controlling cellular excitability, yet the conditions under which endogenous opioid peptides are released and the precise mechanisms by which they affect synaptic transmission remain poorly understood. The opioid peptide dynorphin is present
Hugo A Tejeda et al.
Psychopharmacology, 210(2), 231-240 (2010-03-17)
Kappa-opioid receptor (KOR) agonists produce dysphoria and psychotomimesis in humans. KORs are enriched in the prefrontal cortex and other brain regions that regulate mood and cognitive function. Dysregulation of the dynorphin/KOR system has been implicated in the pathogenesis of schizophrenia
L M Bohn et al.
Journal of neurochemistry, 74(2), 564-573 (2000-01-26)
As reports on G protein-coupled receptor signal transduction mechanisms continue to emphasize potential differences in signaling due to relative receptor levels and cell type specificities, the need to study endogenously expressed receptors in appropriate model systems becomes increasingly important. Here
S Stevens Negus et al.
Psychopharmacology, 210(2), 149-159 (2010-01-27)
Selective, centrally acting kappa opioid agonists produce antinociception in a wide range of preclinical assays, but these compounds perform poorly as analgesics in humans. This discrepancy may be related to the behavioral depressant effects of kappa agonists. Kappa antagonists do
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