Tramadol

Base Information

• Chemical Name: Tramadol
• CAS No.: 2914-77-4
• Deprecated CAS: 73806-46-9,113683-92-4,46941-74-6,113683-92-4
• Molecular Formula: C16H25 N O2
• Molecular Weight: 263.38
• Hs Code.: 2922509090
• European Community (EC) Number: 248-319-6
• UNII: 39J1LGJ30J,0NG5TTM63P
• DSSTox Substance ID: DTXSID90858931,DTXSID401167150
• Nikkaji Number: J28.136K
• Wikipedia: Tramadol
• Wikidata: Q407592
• NCI Thesaurus Code: C29507
• RXCUI: 10689
• Pharos Ligand ID: 62M1Y1V4ZP1L
• Metabolomics Workbench ID: 42601
• ChEMBL ID: CHEMBL1066
• Mol file: 2914-77-4.mol

Synonyms:Adolonta;Amadol;Biodalgic;Biokanol;Contramal;Jutadol;K 315;K-315;K315;MTW Tramadol;MTW-Tramadol;MTWTramadol;Nobligan;Prontofort;Ranitidin 1A Pharma;Takadol;Theradol;Tiral;Topalgic;Tradol;Tradol Puren;Tradol-Puren;TradolPuren;Tradonal;Tralgiol;Trama 1A Pharma;Trama AbZ;Trama Dorsch;Trama KD;Trama-Dorsch;Tramabeta;Tramadin;Tramadoc;Tramadol;Tramadol 1A;Tramadol acis;Tramadol AL;Tramadol Asta Medica;Tramadol Basics;Tramadol Bayvit;Tramadol Bexal;Tramadol Cinfa;Tramadol Dolgit;Tramadol Edigen;Tramadol Hameln;Tramadol Heumann;Tramadol Hydrochloride;Tramadol Kern;Tramadol Lichtenstein;Tramadol Lindo;Tramadol Mabo;Tramadol Normon;Tramadol PB;Tramadol Ratiopharm;Tramadol Stada;Tramadol-Dolgit;Tramadol-Hameln;Tramadol-ratiopharm;TramadolDolgit;TramadolHameln;Tramadolor;Tramadolratiopharm;TramaDorsch;Tramadura;Tramagetic;Tramagit;Tramake;Tramal;Tramex;Tramundin;Trasedal;Ultram;Xymel 50;Zamudol;Zumalgic;Zydol;Zytram

Chemical Property of Tramadol

Chemical Property:

• Refractive Index: 1.4909 (estimate)
• Boiling Point: 388.1°Cat760mmHg
• PKA: 14.47±0.40(Predicted)
• Flash Point: 188.5°C
• PSA: 32.70000
• Density: 1.047g/cm³
• LogP: 2.63460
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 263.188529040
• Heavy Atom Count: 19
• Complexity: 282

Purity/Quality:

99% ^*data from raw suppliers

TRAMADOL IMPURITY A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Opioids
• Canonical SMILES: CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O
• Isomeric SMILES: CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O
• Recent ClinicalTrials: 'NSAIDs vs. Opiates: Which is More Effective in Managing Pain in Mild to Moderate Acute Pancreatitis?
• Recent EU Clinical Trials: Multicentre, randomized, open-label study to prove an additional
• Recent NIPH Clinical Trials: The psychotropic drug dopamine PET study

Technology Process of Tramadol

There total 37 articles about Tramadol 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: 98.0%

tramadol hydrochloride (36282-47-0,22204-88-2) → cis-tramadol (27203-92-5,2914-77-4,73806-46-9,123134-25-8,123154-38-1,36282-47-0,152538-36-8,181289-58-7,181289-59-8)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 0.25h;

Reference yield: 66.0%

rel-(1R,2S)-2-(bromomethyl)-1-(3-methoxyphenyl)cyclohexan-1-ol + dimethyl amine (124-40-3) → cis-tramadol (27203-92-5,2914-77-4,73806-46-9,123134-25-8,123154-38-1,36282-47-0,152538-36-8,181289-58-7,181289-59-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1002/adsc.201901533

Reference yield:

2-[(dimethylamino)methyl]cyclohexanone (769092-24-2) + (3-methoxyphenyl)magnesium bromide (36282-40-3) → (±)-(1R,2S)-2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol (2914-77-4,27203-92-5,73806-46-9,123134-25-8,123154-38-1,152538-36-8,181289-58-7,181289-59-8) + cis-tramadol (27203-92-5,2914-77-4,73806-46-9,123134-25-8,123154-38-1,36282-47-0,152538-36-8,181289-58-7,181289-59-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 0.55h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2010.02.078

upstream raw materials:

2-[(dimethylamino)methyl]cyclohexanone

(3-methoxyphenyl)magnesium bromide

C₁₆H₂₅NO₂*C₈H₈O₃

cis-tramadol

Downstream raw materials:

(±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol

(+)-tramadol*(L)-(+)-mandelic acid

C₁₆H₂₅NO₂*C₈H₈O₃

(-)-tramadol

Refernces

• 1、 Mita, Tsuyoshi,Sato, Yoshihiro,Uchiyama, Masashi. "Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)?H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds". . . Retrieved 2020/02/05.
• 2、 Naghdi, Elahe,Fakhari, Ali Reza. "Simultaneous chiral separation of tramadol and methadone in tablets, human urine, and plasma by capillary electrophoresis using maltodextrin as the chiral selector". . p. 1161 - 1168. Retrieved 2018/09/06.