Metergoline - Moligand™,≥99% , CAS No.17692-51-2

CAS: 17692-51-2 Cat. No.: M768924 Molecular Weight: 403.52 EC Number: 241-686-3 PubChem CID: 28693

GRADE & PURITY Moligand™, ≥99%

Synonyms

D-[(4,6,6a,7,8,9,10,10a-Octahydro-4,7-dimethyl-10aalpha-indolo[4,3-fg]quinolin-9beta-yl)methyl]carbamic acid benzyl ester | FI 6337 | Liserdol | Metergolin | [(8β)-1,6-DiMethylergolin-8-yl)Methyl]carbaMicacidphenylMethylester | METERGOLINE | Benzyl (((6aR

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Metergoline is a serotonin (5-HT) receptor and dopamine receptors antagonist, with pKis of 8.64, 8.75 and 8.75 for 5-HT2A, 5-HT2B and 5-HT2C, respectively. Metergoline is a high-affinity ligand for the h5-HT7 receptor, with a Ki of 16 nM. Metergoline is also a reversible neural Na+ channels inhibitor. Metergoline is commonly used for the research of seasonal affective disorder, prolactin hormone regulation.

Specifications

Synonyms

D-[(4, 6, 6a, 7, 8, 9, 10, 10a-Octahydro-4, 7-dimethyl-10aalpha-indolo[4, 3-fg]quinolin-9beta-yl)methyl]carbamic acid benzyl ester | FI 6337 | Liserdol | Metergolin | [(8β)-1, 6-DiMethylergolin-8-yl)Methyl]carbaMicacidphenylMethylester | METERGOLINE | Benzyl (((6aR

Specifications & Purity

Moligand™, ≥99%

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ANTAGONIST

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CN1CC(CC2C1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5
• IUPAC Name: benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
• InChIKey: WZHJKEUHNJHDLS-QTGUNEKASA-N
• 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
• Isomeric SMILES: CN1C[C@@H](C[C@H]2[C@H]1CC3=CN(C4=CC=CC2=C34)C)CNC(=O)OCC5=CC=CC=C5
• WGK Germany: 1
• RTECS: FA1070000
• PubChem CID: 28693
• Molecular Weight: 403.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Indoloquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Indoloquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Indoloquinolines
• Alternative Parents: Ergoline and derivatives Benzoquinolines Pyrroloquinolines 3-alkylindoles Benzyloxycarbonyls N-alkylindoles Isoindoles and derivatives Aralkylamines Piperidines N-methylpyrroles Carbamate esters Heteroaromatic compounds Trialkylamines Organic carbonic acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Ergoline skeleton - Indoloquinoline - Benzoquinoline - Pyrroloquinoline - Benzyloxycarbonyl - N-alkylindole - 3-alkylindole - Indole - Indole or derivatives - Isoindole or derivatives - Alkaloid or derivatives - Aralkylamine - Benzenoid - Monocyclic benzene moiety - N-methylpyrrole - Substituted pyrrole - Piperidine - Heteroaromatic compound - Carbamic acid ester - Pyrrole - Carbonic acid derivative - Tertiary amine - Tertiary aliphatic amine - Azacycle - Organonitrogen compound - Organic oxide - Amine - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
• External Descriptors: carbamate ester - ergoline alkaloid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Flash Point(°F): 48.2 °F
• Flash Point(°C): 9 °C
• Molecular Weight: 403.500 g/mol
• XLogP3: 3.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 403.226 Da
• Monoisotopic Mass: 403.226 Da
• Topological Polar Surface Area: 46.500 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 607.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1