benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate

• ChemBase ID: 128293
• Molecular Formular: C25H29N3O2
• Molecular Mass: 403.51666
• Monoisotopic Mass: 403.22597718
• SMILES: O=C(OCc1ccccc1)NC[C@@H]1C[C@@H]2c3cccc4c3c(cn4C)C[C@H]2N(C1)C
• Canonical SMILES: O=C(OCc1ccccc1)NC[C@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)cn3C
• InChI: 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
• InChIKey: WZHJKEUHNJHDLS-QTGUNEKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate
• IUPAC Traditional name: benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate; metergoline
• Synonyms: Methergoline; Al-Migren; Liserdol; Metergoline; N-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamine; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester; Metergoline

Database IDs

• CAS Number: 17692-51-2
• EC Number: 241-686-3
• MDL Number: MFCD00153829
• PubChem SID: 162222601; 24278105
• PubChem CID: 28693
• ATC CODE: G02CB05
• CHEMBL: 19215
• Chemspider ID: 26687
• IUPHAR ligand ID: 133
• Unique Ingredient Identifier: 1501393LY5
• Wikipedia Title: Metergoline

CALCULATED PROPERTIES

• Acid pKa: 15.702286
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.3148799
• LogD (pH = 7.4): 3.088585
• Log P: 3.986986
• Molar Refractivity: 119.2987 cm^3
• Polarizability: 47.139015 Å^3
• Polar Surface Area: 46.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble1.4 mg/mL; ethanol: soluble4 mg/mL; H2O: insoluble
• Melting Point: 148-150 °C(lit.)

Safety Information

• RTECS: FA1070000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)rat ... Htr7(65032)
• Mechanism of Action: 5-HT1 antagonist and 5-HT1D ligand; 5-HT2 antagonist; Dopamine agonist; Has moderate affinity for 5-HT6 and high affinity for 5-HT7; Serotonin receptor antagonist

Product Information

• Application(s): Analgesic; Antipyretic; Migraine disorgers therapy
• Empirical Formula (Hill Notation): C25H29N3O2

DETAILS

Sigma Aldrich - M3668

Biochem/physiol Actions
Antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors; analgesic; antipyretic.

REFERENCES

• Bagdy et al (1992) Pharmacological characterization of serotonin receptor subtypes involved in vasopressin and plasma renin activity responses to serotonin agonists. Eur.J.Pharmacol. 210 285.