Metergoline

SIGMA/M3668

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

CAS Number: 17692-51-2
Empirical Formula (Hill Notation): C₂₅H₂₉N₃O₂
Molecular Weight: 403.52
EC Number: 241-686-3
MDL Number: MFCD00153829
Linear Formula: C₂₅H₂₉N₃O₂
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-M3668-500MG	500 mg	$176.00 1/EA	Add To Favorites
45-M3668-5G	5 g	$1640.00 1/EA	Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

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
mp	148-150 °C (lit.)
Quality Level	100
SMILES string	[H][C@]2(CNC(=O)OCc1ccccc1)CN(C)[C@]3([H])Cc4cn(C)c5cccc(c45)[C@@]3([H])C2
solubility	0.1 M HCl: 1.4 mg/mL
	ethanol: 4 mg/mL
	H₂O: insoluble
storage temp.	−20°C

Application:	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
Biochem/physiol Actions:	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.

Symbol	GHS07
Signal word	Warning
Hazard statements	H302 + H312 + H332
Precautionary statements	P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
Hazard Codes	Xn
Risk Statements	20/21/22
Safety Statements	36
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3

mp	148-150 °C (lit.)
Storage Temp.	−20°C
UNSPSC	12352200

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