Lorcaserin hydrochloride

Base Information

• Chemical Name: Lorcaserin hydrochloride
• CAS No.: 846589-98-8
• Molecular Formula: C11H14 Cl N . Cl H
• Molecular Weight: 232.153
• Hs Code.: 2933990090
• UNII: 0QJF08GDPE
• ChEMBL ID: CHEMBL2095211
• DSSTox Substance ID: DTXSID60233650
• NCI Thesaurus Code: C76103
• Wikidata: Q27888442
• Mol file: 846589-98-8.mol

Synonyms:(1R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine;8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine;APD 356;APD-356;APD356;AR-10A;Belviq;lorcaserin

Chemical Property of Lorcaserin hydrochloride

Chemical Property:

• PSA: 12.03000
• LogP: 3.72000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 231.0581549
• Heavy Atom Count: 14
• Complexity: 172

Purity/Quality:

99%+ ^*data from raw suppliers

LorcaserinHydrochloride 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNCCC2=C1C=C(C=C2)Cl.Cl
• Isomeric SMILES: C[C@H]1CNCCC2=C1C=C(C=C2)Cl.Cl
• Recent ClinicalTrials: Lorcaserin in Obesity: Identification of CNS Targets Using fMRI
• Recent EU Clinical Trials: A Randomized, Double-Blind, Placebo-Controlled, Parallel-Group Study to Evaluate the Effect of Long-Term Treatment with BELVIQ (lorcaserin HCl) on the Incidence of Major Adverse Cardiovascular Events and Conversion to Type 2 Diabetes Mellitus in Obese and Overweight Subjects with Cardiovascular Disease or Multiple Cardiovascular Risk Factors
• Description: In June 2012, the US FDA approved lorcaserin for chronic weight management in adult patients who are characterized as overweight or obese and have at least one comorbid, weight-related condition. Lorcaserin (also known as APD356) is the first 5-HT2C agonist approved for chronic weight management since the withdrawal of the 5-HT2C agonist fenfluramine in 1997 due to rare cases of cardiac valvulopathy. The serotonin receptor 5-HT2C is found primarily in the hypothalamus and regulates appetite and feeding behavior. Safety issues with fenfluramine were associated with poor selectivity for 5-HT2C versus 5HT2A and 5HT2B. Ring constraint afforded by the benzazepine in lorcaserin improved selectivity for 5HT2C by over 2 log units. Lorcaserin (hydrochloride) (CRM) (Item No. 19247) is a certified reference material categorized as an anorectic. It also decreases oxycodone intake and has positive effects on self-administration and relapse vulnerability in the rat. Lorcaserin is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.
• Uses: Lorcaserin hydrochloride, a novel antiobesity drug, is a selective serotonin 5-HT2C receptor agonist, approved by FDA in 2012.

Technology Process of Lorcaserin hydrochloride

There total 51 articles about Lorcaserin 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: 98.6%

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate (824430-78-6,847063-12-1) → Lorcaserin hydrochloride (846589-98-8,1006037-59-7)

Guidance literature:

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine L-(+)-tartrate; With sodium hydroxide; In dichloromethane; water; at 10 - 30 ℃; for 1h;

With hydrogenchloride; In ethyl methyl ether; at 0 - 10 ℃; pH=1.5 - 2.5;

Reference yield: 98.0%

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate (824430-78-6,847063-12-1) → Lorcaserin hydrochloride (846589-98-8,1006037-59-7)

Guidance literature:

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate; With potassium carbonate; In water; ethyl acetate; at 15 ℃; Large scale;

With hydrogenchloride; In water; ethyl acetate; pH=<= 5; Temperature; Large scale;

Reference yield: 98.0%

lorcaserin (616202-92-7) → Lorcaserin hydrochloride (846589-98-8,1006037-59-7)

Guidance literature:

With hydrogenchloride; In methanol; water; at 0 - 5 ℃; Solvent; Concentration;

upstream raw materials:

bis((R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine) L-(+)-tartarate

8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine L-hemitartrate

lorcaserin

(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hemitartrate

Downstream raw materials:

N-Hydroxylorcaserin

3-methoxy-1-((R)-1-methyl-8-(4-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)phenyl)-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)propan-1-one

(R)-1-(8-chloro-1-methyl-4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)ethanone

Refernces

• 1、 -. "Method for preparing lorcaserin". Paragraph 0035; 0037-0039; 0041-0043. . Retrieved 2020/08/22.
• 2、 Ghotekar, Ganesh S.,More, Devidas A.,Nalla, Viswanadh,Muthukrishnan. "A new enantioselective synthesis of antiobesity drug lorcaserin". . p. 16876 - 16880. Retrieved 2019/11/14.