M3668

Metergoline

Name: Metergoline
Brand: SIGMA

别名:

N-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamine, [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester

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About This Item

经验公式（希尔记法）:

C₂₅H₂₉N₃O₂

CAS Number:

17692-51-2

分子量:

403.52

EC 号:

241-686-3

MDL编号:

MFCD00153829

UNSPSC代码:

12352200

PubChem化学物质编号:

24278105

NACRES:

NA.77

主要文件

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质量水平

100

mp

148-150 °C (lit.)

溶解性

0.1 M HCl: 1.4 mg/mL
ethanol: 4 mg/mL
H₂O: insoluble

储存温度

−20°C

SMILES字符串

[H][C@]2(CNC(=O)OCc1ccccc1)CN(C)[C@]3([H])Cc4cn(C)c5cccc(c45)[C@@]3([H])C2

InChI

1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1

InChI key

WZHJKEUHNJHDLS-QTGUNEKASA-N

基因信息

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)
rat ... Htr7(65032)

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应用

Metergoline has been used as a serotonin receptor antagonist:

to study its effects on astrocyte calcium signals evoked by whisker stimulation
to study its effects on lipopolysaccharide-induced anorexia in rats
to evaluate the non-specific binding by 5-HT_1A receptor binding assays

生化/生理作用

Metergoline is an ergot alkaloid and a selective serotonin antagonist which blocks the 5-HT_2A and 5-HT_2C receptors with higher affinity. It possesses antifungal activity against infection caused by Candida krusei. Metergoline exhibits a therapeutic effect against premenstrual dysphoric disorder. It also exhibits antipyretic and analgesic activities.