Lorcaserin

Base Information

• Chemical Name: Lorcaserin
• CAS No.: 616202-92-7
• Molecular Formula: C₁₁H₁₄ClN
• Molecular Weight: 195.692
• Hs Code.: 2933990090
• European Community (EC) Number: 809-254-4
• UNII: 637E494O0Z
• ChEMBL ID: CHEMBL360328
• DSSTox Substance ID: DTXSID3048659
• Metabolomics Workbench ID: 63805
• NCI Thesaurus Code: C76102
• Nikkaji Number: J3.095.767I
• Pharos Ligand ID: C2RNZVF18AKN
• Wikidata: Q340139
• Wikipedia: Lorcaserin
• Mol file: 616202-92-7.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

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Lorcaserin

Chemical Property:

• Appearance/Colour: yellow oil
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 288.125 °C at 760 mmHg
• PKA: 9.99±0.40(Predicted)
• Flash Point: 128.054 °C
• PSA: 12.03000
• Density: 1.075 g/cm³
• LogP: 2.91800
• Storage Temp.: -20?C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 195.0814771
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Weight Loss Agents
• Canonical SMILES: CC1CNCCC2=C1C=C(C=C2)Cl
• Isomeric SMILES: C[C@H]1CNCCC2=C1C=C(C=C2)Cl
• Recent ClinicalTrials: A Study of Lorcaserin as Adjunctive Treatment in Participants With Dravet Syndrome
• 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
• Drug Interactions: Due to the theoretical possibility of the mechanism of lorcaserin and serotonin syndrome, when lorcaserin is used in combination with the serotonergic neurotransmitter system drugs, extreme caution should be paid, including triptans monoamine oxidase inhibitor agent selective serotonin reuptake inhibitor selective serotonin and norepinephrine reuptake inhibitors, tricyclic antidepressants bupropion dextromethorphan, lithium tramadol and St. John's wort , etc. In addition, when the present product with CYP2D6 substrates when combined with the need to be cautious, because the product can increase the exposure of these drugs. The above information is edited by the lookchem of Tian Ye.
• Uses: diet pills. Lorcaserin was used to treat Opioid Use Disorder (OUD). Lorcaserin was used to treat Opioid Use Disorder (OUD). A novel selective 5-HT2C-receptor agonist for the treatment of obesity.

Technology Process of Lorcaserin

There total 74 articles about Lorcaserin 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: 99.0%

(1S)-N-trifluoroacetyl-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (616202-78-9) → (S)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (616202-81-4,616202-92-7)

Guidance literature:

With methanol; sodium hydroxide; water; at 20 ℃; for 2.66667h;

Reference yield: 99.0%

1-[[2-(4-chlorophenyl)ethyl]amino]-2-chloropropane hydrochloride (953789-37-2) → (+/-)-Lorcaserin (616201-80-0,616202-92-7)

Guidance literature:

With aluminum (III) chloride; In 1,2-dichloro-benzene; at 120 - 125 ℃; Inert atmosphere;

Reference yield: 92.3%

N-(4-chlorophenylethyl)propyl-2-ene-1-amine hydrochloride → (+/-)-Lorcaserin (616201-80-0,616202-92-7)

Guidance literature:

With aluminum (III) chloride; In 1,2-dichloro-benzene; at 110 ℃; for 4h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere; Large scale;

DOI:10.1021/acs.oprd.5b00144

upstream raw materials:

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

N-(4-chlorophenylethyl)-2-chloropropanamide

4-chlorophenylethylamine

1-(8-chloro-1-methyl-1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)-2,2,2-trifluoroethan-1-one

Downstream raw materials:

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

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

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

(±)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride

Refernces

Discovery of a novel azepine series of potent and selective 5-HT_2C agonists as potential treatments for urinary incontinence

10.1016/j.bmcl.2009.07.063

Paul E. Brennan et al. details the development of a new series of azepine compounds designed to treat urinary incontinence by acting as selective 5-HT2C receptor agonists. Lorcaserin and valbiferin are azapine derivatives that were used as reference compounds in the study of selective 5-HT2C agonists. The researchers synthesized a range of heterocycle-fused azepines, starting with pyridazo-azepines which showed good potency but lacked selectivity against 5-HT2B. Further modifications led to the discovery of triazolopyrimido-azepines, with compound 36 emerging as a potent, selective, and metabolically stable candidate that demonstrated efficacy in an in vivo model of stress urinary incontinence. The study underscores the importance of computational and in vitro models in guiding the design of compounds with desirable pharmacokinetic properties, such as good blood-brain barrier penetration and minimal P-glycoprotein-mediated efflux.