Mepyramine

Base Information

• Chemical Name: Mepyramine
• CAS No.: 91-84-9
• Deprecated CAS: 102206-59-7
• Molecular Formula: C17H23 N3 O
• Molecular Weight: 285.389
• European Community (EC) Number: 202-102-2
• NSC Number: 13136
• UNII: HPE317O9TL
• DSSTox Substance ID: DTXSID9023542
• Nikkaji Number: J4.645K
• Wikipedia: Mepyramine
• Wikidata: Q3800087
• NCI Thesaurus Code: C76676
• RXCUI: 9009
• Pharos Ligand ID: DDDT8BRX79A1
• Metabolomics Workbench ID: 43674
• ChEMBL ID: CHEMBL511
• Mol file: 91-84-9.mol

Synonyms:Anthisan;Boots Bite and Sting Relief;Kriptin;Maleate, Mepyramine;Maleate, Pyrilamine;Mepyramine;Mepyramine Maleate;Pyranisamine;Pyrilamine;Pyrilamine Maleate

Chemical Property of Mepyramine

Chemical Property:

• Refractive Index: nD25 1.5760-1.5765
• Boiling Point: bp5 201°; bp0.06 168-172°
• PKA: pKa 4.02(H2O t=25 c=0.002 to 0.01) (Uncertain);8.92 (Uncertain)
• PSA: 28.60000
• Density: 1.0141 (rough estimate)
• LogP: 2.65840
• Water Solubility.: 3.425g/L(37.5 oC)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 285.184112366
• Heavy Atom Count: 21
• Complexity: 277

Purity/Quality:

99.9% ^*data from raw suppliers

N1-(4-Methoxybenzyl)-N2,N2-dimethyl-N1-(pyridin-2-yl)ethane-1,2-diamine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2
• Uses: Antihistaminic. Pyrilamine is also used for allergy symptoms and rhinitis. N1-(4-Methoxybenzyl)-N2,N2-dimethyl-N1-(pyridin-2-yl)ethane-1,2-diamine also known as pyrilamine works in synergism with diclofenac as a therapeutic alternative for clinical management of inflammatory pain.

Technology Process of Mepyramine

There total 8 articles about Mepyramine 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: 84.0%

2-chloropyridine (109-09-1) + N1-(4-methoxybenzyl)-N2,N2-dimethylethane-1,2-diamine (65875-39-0) → pyrilamine (91-84-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; sodium tert-pentoxide; In toluene; at 80 ℃; for 18h; Schlenk technique; Glovebox;

DOI:10.1021/acs.orglett.0c04101

Reference yield: 82.0%

N,N-dimethyl-N'-(pyridine-2-yl)ethane-1,2-diamine (23826-72-4) + 4-Methoxybenzyl alcohol (105-13-5) → pyrilamine (91-84-9)

Guidance literature:

With W₄ Raney Nickel; In 5,5-dimethyl-1,3-cyclohexadiene; for 30h; Reflux;

DOI:10.1016/j.apcata.2014.04.009

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → pyrilamine (91-84-9)

Guidance literature:

With toluene;

DOI:10.1021/ja01214a037

upstream raw materials:

2-(dimethylamino)ethyl chloride

p-Methoxybenzyl bromide

p-methoxybenzyl chloride

N,N-dimethyl-N'-(pyridine-2-yl)ethane-1,2-diamine

Downstream raw materials:

((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-{2-[(4-methoxy-benzyl)-pyridin-2-yl-amino]-ethyl}-dimethyl-ammonium; chloride

N-Desmethylpyrilamine

(5-(1-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)propan-2-ylamino)-1H-indol-2-yl)(4-methylpiperazin-1-yl)methanone

1-((2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)(methyl)amino)propan-2-one

Refernces

• 1、 Mehta, Astha,Thaker,Londhe,Nandan, Santosh R.. "Reinvestigating Raney nickel mediated selective alkylation of amines with alcohols via hydrogen autotransfer methodology". . p. 241 - 251. Retrieved 2014/05/20.