Quinagolide hydrochloride

Base Information

• Chemical Name: Quinagolide hydrochloride
• CAS No.: 94424-50-7
• Molecular Formula: C₂₀H₃₃N₃O₃S*ClH
• Molecular Weight: 432.027
• DSSTox Substance ID: DTXSID20241478
• Wikipedia: Quinagolide
• NCI Thesaurus Code: C73310
• Mol file: 94424-50-7.mol

Synonyms:CV 205-502;CV-205-502;CV205-502;N,N-diethyl-N'-(1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzo(g)quinolinyl)sulfamide hydrochloride, (3alpha,4aalpha,10abeta)-(+)-isomer;N,N-diethyl-N'-(1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzo(g)quinolinyl)sulfamide, (3alpha,4aalpha,10abeta)-(+-)-isomer;Norprolac;quinagolide;quinagolide hydrochloride;quinagolide hydrochloride, (3alpha,4aalpha,10abeta)-(+)-isomer;quinagolide hydrochloride, 3alpha,4aalpha,10abeta-(-)-isomer;quinagolide, (3alpha,4aalpha,10abeta)-(+-)-isomer

Chemical Property of Quinagolide hydrochloride

Chemical Property:

• Vapor Pressure: 3.11E-12mmHg at 25°C
• Melting Point: 234-236°
• Boiling Point: 539.1°C at 760 mmHg
• Flash Point: 279.8°C
• PSA: 81.26000
• LogP: 4.34770
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 431.2009408
• Heavy Atom Count: 28
• Complexity: 576

Purity/Quality:

99%min ^*data from raw suppliers

QuinagolideHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1CC(CC2C1CC3=C(C2)C(=CC=C3)O)NS(=O)(=O)N(CC)CC.Cl
• Isomeric SMILES: CCCN1C[C@H](C[C@H]2[C@H]1CC3=C(C2)C(=CC=C3)O)NS(=O)(=O)N(CC)CC.Cl
• Recent ClinicalTrials: Study Assessing the Effect of 3-week Treatment With One of Three Oral Doses of Quinagolide
• Recent EU Clinical Trials: A randomised, double-blind, placebo-controlled, proof-of-mechanism phase 2 trial investigating the effect of quinagolide extended-release vaginal ring on reduction of lesions assessed by high-resolution magnetic resonance imaging in women with endometrioma, deep infiltrating endometriosis, and/or adenomyosis
• Description: Quinagolide is a potent and specific non-ergot dopamine D2 agonist launched in the Netherlands for the treatment of hyperprolactinemia. Quinagolide is effective in inhibiting prolactin secretion by human pituitary tumor and hyperprolactinemia in vitro and in viva A daily dose of as low as 60 pg is able to achieve a pronounced and prolonged suppressive effect on serum prolactin and growth hormone secretion. It is also effective in providing relief from associated effects such as infertility, galactorrhea, oligomenorrhea, amenorrhea, loss of IibMo and impotence. Compared with the most widely used antiprolactin, bromocriptine, quinagolide is more potent in vivo with a longer duration of action and fewer side effects. A recent study showed that acute administration of quinagolide suppresses growth hormone secretion in acromegalic patients and thus could serve as an alternative therapy in acromegaly.
• Uses: Quinagolide is a nonergot dopamine D2-receptor agonist. Quinagolide acts as an prolactin inhibitor.

Technology Process of Quinagolide hydrochloride

There total 6 articles about Quinagolide hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

(+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-1-propyl-3-benzoquinolinyl>sulfamide (87056-75-5) → (+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzoquinolinyl>sulfamide hydrochloride (94424-50-7)

Guidance literature:

(+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-1-propyl-3-benzoquinolinyl>sulfamide; With aluminum (III) chloride; ethanethiol; In dichloromethane; at 25 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In diethyl ether; dichloromethane; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02900

Reference yield:

C20H29NO4 → (+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzoquinolinyl>sulfamide hydrochloride (94424-50-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium azide / acetonitrile; methanol / 0.25 h / Inert atmosphere

1.2: 0 - 25 °C / Inert atmosphere

2.1: sodium cyanoborohydride / ethanol / 0.33 h / 0 °C / Inert atmosphere

2.2: 12 h / 0 - 25 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 50 °C / Inert atmosphere

3.2: 2.5 h / 50 °C / Inert atmosphere

4.1: triphenylphosphine; water / tetrahydrofuran / 5 h / Reflux; Inert atmosphere

5.1: triethylamine / chloroform / 12 h / 50 °C

6.1: aluminum (III) chloride; ethanethiol / dichloromethane / 12 h / 25 °C / Inert atmosphere

6.2: Inert atmosphere

With aluminum (III) chloride; sodium azide; water; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; ethanethiol; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.8b02900

Reference yield:

C20H28N4O4 → (+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzoquinolinyl>sulfamide hydrochloride (94424-50-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium cyanoborohydride / ethanol / 0.33 h / 0 °C / Inert atmosphere

1.2: 12 h / 0 - 25 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.33 h / 50 °C / Inert atmosphere

2.2: 2.5 h / 50 °C / Inert atmosphere

3.1: triphenylphosphine; water / tetrahydrofuran / 5 h / Reflux; Inert atmosphere

4.1: triethylamine / chloroform / 12 h / 50 °C

5.1: aluminum (III) chloride; ethanethiol / dichloromethane / 12 h / 25 °C / Inert atmosphere

5.2: Inert atmosphere

With aluminum (III) chloride; water; sodium cyanoborohydride; potassium carbonate; triethylamine; triphenylphosphine; ethanethiol; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/acs.orglett.8b02900

upstream raw materials:

(+/-)-N,N-diethyl-N'-<(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-1-propyl-3-benzoquinolinyl>sulfamide

Refernces