Promethazine

Base Information

• Chemical Name: Promethazine
• CAS No.: 60-87-7
• Deprecated CAS: 73745-50-3
• Molecular Formula: C17H20 N2 S
• Molecular Weight: 284.425
• Hs Code.: 2934300000
• European Community (EC) Number: 200-489-2
• NSC Number: 30321
• UNII: FF28EJQ494
• DSSTox Substance ID: DTXSID7023518
• Nikkaji Number: J4.809G
• Wikipedia: Promethazine
• Wikidata: Q422970
• NCI Thesaurus Code: C779
• RXCUI: 8745
• Pharos Ligand ID: H1LMQZFW5RCR
• Metabolomics Workbench ID: 43306
• ChEMBL ID: CHEMBL643
• Mol file: 60-87-7.mol

Synonyms:Atosil;Diphergan;Diprazin;Hydrochloride, Promethazine;Isopromethazine;Phenargan;Phenergan;Phensedyl;Pipolfen;Pipolphen;Proazamine;Promet;Prometazin;Promethazine;Promethazine Hydrochloride;Prothazin;Pyrethia;Remsed;Rumergan

Chemical Property of Promethazine

Chemical Property:

• Melting Point: 60
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 190-192oC at 3 mm Hg
• PKA: pKa 9.1(H2O,t undefined) (Uncertain)
• PSA: 31.78000
• Density: 1.131
• LogP: 4.30440
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: 383.9ug/L(22.5 oC)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 284.13471982
• Heavy Atom Count: 20
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

N,N-dimethyl-1-(10H-phenothiazin-10-yl)-2-propanamine AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antihistamines
• Canonical SMILES: CC(CN1C2=CC=CC=C2SC3=CC=CC=C31)N(C)C
• Recent ClinicalTrials: Treatment of Pruritus With Intramuscular Promethazine
• Description: As a derivative of phenothiazine, promethazine is structurally and pharmacologically similar to chlorpromazine. It exhibits strong antihistamine activity as well as expressed action on the CNS. It potentiates action of sedative and analgesic drugs.
• Uses: Promethazine is used for treating allergic illnesses such as hives, serum disease, hay fever, dermatosis, and also for rheumatism with expressed allergic components, for allergic complications caused by antibiotics and other medicinal drugs, and for enhancing action of analgesics and local anesthetics. Synonyms of this drug are allergen, phenergan, pipolphen, prothazine, and others. Promethazine is used in preparation of antibodies having inhibitory activities to IL-36R signaling triggered by agonistic ligands and application to prevention and therapies of cancers and autoimmune diseases. Anti-emetic; antihistaminic.
• Clinical Use: Promethazine, an early agent in the series, has many useful pharmacological affects other than being an antihistamine. It has significant antiemetic and anticholinergic properties. It also has sedative-hypnotic properties and has been used to potentiate the effects of analgesic drugs. Subsequent analogues, such as trimeprazine and methdilazine, are used as antipruritic agents in the treatment of urticaria.

Technology Process of Promethazine

There total 23 articles about Promethazine 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: 96.0%

phenergan (58-33-3) → 10-[2-(dimethylamino)propyl]phenothiazine (60-87-7)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; Reagent/catalyst;

Reference yield: 75.0%

N,N-dimethylammonium chloride (506-59-2) + 1-(10H-phenothiazin-10-yl)propan-2-one (15375-56-1) → 10-[2-(dimethylamino)propyl]phenothiazine (60-87-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In N,N-dimethyl acetamide; at 50 ℃; for 120h;

DOI:10.3390/molecules26082182

Reference yield: 75.0%

dimethyl amine (124-40-3) + 1-(10H-phenothiazin-10-yl)propan-2-one (15375-56-1) → 10-[2-(dimethylamino)propyl]phenothiazine (60-87-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; In N,N-dimethyl acetamide; at 50 ℃;

upstream raw materials:

10H-phenothiazine

2-chloro-1-dimethylaminopropane

(2-chloro-1-methyl-ethyl)-dimethyl-amine

2-(dimethyl-amino)-1-methylethylchloride hydrochloride

Downstream raw materials:

antipyrine

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-dimethyl-(1-methyl-2-phenothiazin-10-yl-ethyl)-ammonium; chloride

promethazine cation radical

catechin

Refernces

• 1、 -. "AMYLOID-BINDING COMPOUNDS AND METHODS OF USE THEREOF". . . Retrieved 2021/01/25.
• 2、 Chen, Jieping,Shen, Xuzhong,Lu, Zhan. "Cobalt-Catalyzed Markovnikov Selective Sequential Hydrogenation/Hydrohydrazidation of Aliphatic Terminal Alkynes". supporting information. p. 14455 - 14460. Retrieved 2020/10/13.