CAS 17692-51-2|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...

General Information

Structure

Molecular Formula

C₂₅H₂₉N₃O₂

Molecular Mass

403.51666

Exact Mass

403.22597718

Charge

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

Canonic Smiles

O=C(OCc1ccccc1)NC[C@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)cn3C

Isomeric Smiles

O=C(OCc1ccccc1)NC[C@@H]1C[C@@H]2c3cccc4c3c(cn4C)C[C@H]2N(C1)C

Calculated Properties

JChem

LogD (pH = 7.4)

3.11

LogD (pH = 5.5)

1.33

Log P

3.99

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

8.22

Polar Surface Area

46.50

Polarizability

46.81

Molar Refractivity

119.30

LOG S

-3.51

Data Source

Names and Identifiers

IUPAC name

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 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

IUPAC Traditional name

metergoline 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 benzyl N-{[(2R,4S,7R)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl}carbamate

Synonyms

Metergoline[(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl esterN-CBZ-[(8β)-1,6-Dimethylergolin-8-yl]methylamineMetergolineMethergolineLiserdolAl-Migren(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid benzyl esterMetergolin(+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline1-Methyl-N-carbobenzyloxydihydro-D-lysergaminD-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl ester1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergolinemetergolineD-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline benzyl ester

International Nonproprietary Name (INN)

metergolinametergolinemetergolinum

Names and Identifiers

Registration numbers

CHEMBL

19215CHEMBL19215

Unique Ingredient Identifier

Wikipedia Title

Chemspider ID

ATC CODE

PubChem CID

CAS Number

IUPHAR ligand ID

PubChem SID

24278105162222601135610975

EC Number

241-686-3

MDL Number

MFCD00153829

PubMed Citation Links

21354537208452631953965622218419241346301950921919484723189969711953851821475142204513982188003319945477216009591963227620377624

ACToR Database

BindingDB Database

KEGG DRUG Database

CHEBI ID

MetaboLights Database

MTBLS2871

SureChEMBL Database

SCHEMBL117882

Drug Central Database

CompTox Database

Reaxys Registry

LINCS Database

Registration numbers

Properties

Physical Property

Melting Point

148-150 °C(lit.)

Solubility

0.1 M HCl: soluble1.4 mg/mL

ethanol: soluble4 mg/mL

H2O: insoluble

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

Dopamine agonist

5-HT2 antagonist

5-HT1 antagonist and 5-HT1D ligand

Serotonin receptor antagonist

Has moderate affinity for 5-HT6 and high affinity for 5-HT7

Product Information

Empirical Formula (Hill Notation)

C25H29N3O2

Application(s)

Analgesic

Migraine disorgers therapy

Antipyretic

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

M3668

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

An ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7.

Molecule Details

References

PubChem Literature

From Data Sources

• 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.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

IUPAC Traditional name

Synonyms

International Nonproprietary Name (INN)

metergolinametergolinemetergolinum

Registration numbers

CHEMBL

19215CHEMBL19215

Unique Ingredient Identifier

Wikipedia Title

Chemspider ID

ATC CODE

PubChem CID

CAS Number

IUPHAR ligand ID

PubChem SID

24278105162222601135610975

EC Number

241-686-3

MDL Number

MFCD00153829

PubMed Citation Links

21354537208452631953965622218419241346301950921919484723189969711953851821475142204513982188003319945477216009591963227620377624

ACToR Database

BindingDB Database

KEGG DRUG Database

CHEBI ID

MetaboLights Database

MTBLS2871

SureChEMBL Database

SCHEMBL117882

Drug Central Database

CompTox Database

Reaxys Registry

LINCS Database

Properties

Physical Property

Melting Point

148-150 °C(lit.)

Solubility

0.1 M HCl: soluble1.4 mg/mL

ethanol: soluble4 mg/mL

H2O: insoluble

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

Dopamine agonist

5-HT2 antagonist

5-HT1 antagonist and 5-HT1D ligand

Serotonin receptor antagonist

Has moderate affinity for 5-HT6 and high affinity for 5-HT7

Product Information

Empirical Formula (Hill Notation)

C25H29N3O2

Application(s)

Analgesic

Migraine disorgers therapy

Antipyretic

Molecule Details

Sigma Aldrich

M3668

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

References

PubChem Literature

From Data Sources

• 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.

Bioactivity

PubChem BioAssay

Molecule

ID:128293