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Metergoline

Metergoline structure

CAS No:
17692-51-2
Formula:
C25H29N3O2
Chemical Name:
Metergoline
Synonyms:
Carbamic acid,N-[[(8β)-1,6-dimethylergolin-8-yl]methyl]-,phenylmethyl ester;Carbamic acid,[(1,6-dimethylergolin-8β-yl)methyl]-,benzyl ester;Carbamic acid,[[(8β)-1,6-dimethylergolin-8-yl]methyl]-,phenylmethyl ester;Lysergamine,N-carboxy-9,10-dihydro-1-methyl-,benzyl ester;Indolo[4,3-fg]quinoline,carbamic acid deriv.;Ergoline,carbamic acid deriv.;(+)-N-Carboxy-1-methyl-9,10-dihydrolysergamide benzyl ester;Metergoline;8β-Carbobenzyloxyaminomethyl-1,6-dimethyl-10α-ergoline;Methergoline;AHR 3009;D-8β-[(Carbobenzoxyamino)methyl]-1,6-dimethyl-10α-ergoline;D-N-Carbobenzoxydihydro-1-methyllysergamine I;D-8β-[(Carboxyamino)methyl]-1,6-dimethylergoline I benzyl ester;D-N-Carboxydihydro-1-methyllysergamine I benzyl ester;D-[(4,6,6a,7,8,9,10,10a-Octahydro-4,7-dimethyl-10aα-indolo[4,3-fg]quinolin-9β-yl)methyl]carbamic acid benzyl ester;Liserdol;Metergolin;MCE;Contralac;FI 6337
Categories:
Active Pharmaceutical Ingredients > Hormones and the Endocrine System

Description

White Solid

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 serotonergic antagonist, a dopamine agonist and a geroprotector. It is an ergoline alkaloid and a carbamate ester.|Metergoline is an ergot-derived psychoactive drug that acts as a ligand for serotonin and dopamine receptors. Metergoline is an antagonist at various 5-HT receptor subtypes at a relatively low concentration and agonist at dopamine receptors. Its use has been studied in various clinical settings such as a treatment for seasonal affective disorder, prolactin hormone regulation due to its inhibitory effect on prolactin release, premenstrual dysphoric disorder in women and antianxiety treatment.|A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.

Metergoline Basic Attributes

Molecular Weight：

403.52

Exact Mass：

403.52

EC Number：

241-686-3

UNII：

1501393LY5

DSSTox ID：

DTXSID5042584

ATC Code：

G - Genito urinary system and sex hormones

Characteristics

PSA：

46.5

XLogP3：

4.39350

Density：

1.25±0.1 g/cm3(Predicted)

Melting Point：

146-149 °C

Boiling Point：

612.5±55.0 °C(Predicted)

Flash Point：

324.2ºC

Water Solubility：

0.1 M HCl: 1.4 mg/mL

Storage Conditions：

−20°C

Toxicity：

LD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta)

Specific rotation：

D28 -7 ±2°

Collision Cross Section：

197.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

20/21/22

safety instructions：

RTECS Number：

FA1070000

Marks：

Precautionary statement(s)：

P280

Hazard Statements：

H302-H312-H332

GHS Classification：

|Warning|H302+H312+H332 (79.19%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 197 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)|Drugs that bind to and activate dopamine receptors. (See all compounds classified as Dopamine Agonists.)

MeSH Entry Terms：

Liserdol

Metergoline Use and Manufacturing

Metergoline is an antagonist at 5-HT1, 5-HT2, and 5-HT7 serotonin receptors. Metergoline is an analgesic; antipyretic.

Computed Properties

Molecular Weight:403.5
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:403.22597718
Monoisotopic Mass:403.22597718
Topological Polar Surface Area:46.5
Heavy Atom Count:30
Complexity:607
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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