Basic information
- CAS
17692-51-2- Standard SMILES
CN1C[C@H](CNC(=O)OCc2ccccc2)C[C@@H]2c3cccc4c3c(cn4C)C[C@H]21- InChIKey
WZHJKEUHNJHDLS-QTGUNEKASA-N- Molecular formula
- C25H29N3O2
- Average molar mass
- 403.5 g/mol
- Monoisotopic mass
- 403.22597718
Overview
Metergoline is 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. It has a role as a geroprotector, a serotonergic antagonist and a dopamine agonist. It is a carbamate ester and an ergoline alkaloid.
Names & identifiers
- Preferred name
- Metergoline
- IUPAC
- benzyl N-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
- English name
- METERGOLINE
- Molecular formula
- C25H29N3O2
- Molecular weight
- 403.52
Names & synonyms
metergoline17692-51-2LiserdolMetergolinMethergolineMetergolinaMetergolinumDTXSID5042584FI 6337FI-6337(+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester1-Methyl-N-carbobenzyloxydihydro-D-lysergamin
Show more names
mceahr3009LyserdolMETERGOLINE, INTERNALMETERGOLINE USP/EP/BP
1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergolineD-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline(((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl esterNSC-7558781501393LY5DTXCID3022584CHEBI:64216
Database identifiers
- CAS
17692-51-2- PubChem CID
- 28693
- DTXSID
DTXSID5042584- ChEMBL
CHEMBL19215- ChEBI
CHEBI:64216- UNII
- 1501393LY5
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 607
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section
197.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
196.35 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 148 · 148-150 °C(lit.)
- alpha
- 28 · D28 -7 ±2°
- Boiling point
- 612.5 · 612.5±55.0 °C(Predicted)
- Density
- 1.25 · 1.25±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 0.1 M · 0.1 M HCl: 1.4 mg/mL
- pka
- 12.45 · 12.45±0.46(Predicted)
- form
- solid
- color
- White
- Merck
- 13 · 13,5962
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethaqnol may be stored at -20°C for up to 2 month.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Carbamic acid, (8.beta.)-1,6-dimethylergolin-8-ylmethyl-, phenylmethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- FA1070000
- Toxicity
- LD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta)
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
Chemistry & industry
Pharmacology
ATC Code
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
MeSH Pharmacological Classification
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.
Drugs that bind to and activate dopamine receptors.
Applications
DescriptionMetergoline (17692-51-2) is an ergot alkaloid derivative acting as antagonist at serotonin 5HT1 and 5HT2 receptors1,2 and 5HT7 receptors3. A safe and effective agent for management of hyperprolactinemic amenorrhea and anovulation.4 Displays a long-lasting antidepressant effect in seasonal affective disorder.5
UsesMetergoline is an antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors. Metergoline is an analgesic; antipyretic.
Upstream & downstream products
Upstream raw materials
Suppliers55 total
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
中梦研（湖北）科技有限公司0717-6300888 18062399888 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…