Amitriptynol

Base Information

• Chemical Name: Amitriptynol
• CAS No.: 1159-03-1
• Molecular Formula: C20H25NO
• Molecular Weight: 295.425
• Hs Code.: 2922199695
• European Community (EC) Number: 214-594-6
• UNII: 67H6DX3NOO
• DSSTox Substance ID: DTXSID10151214
• Nikkaji Number: J42.182K
• Wikidata: Q27264131
• ChEMBL ID: CHEMBL1564657
• Mol file: 1159-03-1.mol

Synonyms:1159-03-1;Amitriptynol;5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ol;Amitriptyline Impurity B;5-(3-DIMETHYLAMINOPROPYL)-10,11-DIHYDRO-5H-DIBENZO[A,D]CYCLOHEPTEN-5-OL;EINECS 214-594-6;UNII-67H6DX3NOO;BRN 2148173;67H6DX3NOO;5-(3-Dimethylaminopropyl)5-dibenzo(a,d)cycloheptadienol;5-(3-Dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol;10,11-Dihydro-5-(3-dimethylaminopropyl)-5H-dibenzo(a,d)cyclohepten-5-ol;5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ol;5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol;5H-Dibenzo(a,d)cyclohepten-5-ol, 5-(3-(dimethylamino)propyl)-10,11-dihydro-;2-[3-(dimethylamino)propyl]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ol;5H-DIBENZO(a,d)CYCLOHEPTEN-5-OL, 10,11-DIHYDRO-5-(3-DIMETHYLAMINOPROPYL)-;EC 214-594-6;5-(3-Dimethylaminopropyl)-10,11-dihydrodibenzo(a,d)cyclohepten-5-ol;5H-Dibenzo[a,d]cyclohepten-5-ol, 5-[3-(dimethylamino)propyl]-10,11-dihydro-;11-[3-(dimethylamino)propyl]-5,6-dihydrodibenzo[2,1-b:1',2'-e][7]annulen-11-ol;5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZO(A,D)(7)ANNULEN-5-OL;5H-Dibenzo[a,d]cyclohepten-5-ol, 10,11-dihydro-5-(3-dimethylaminopropyl)-;5-(3-Dimethylamino-propyl)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol;Oprea1_247281;Oprea1_843827;CBDivE_012358;MLS000689024;CHEMBL1564657;SCHEMBL11252431;DTXSID10151214;HMS1683L02;HMS2651H03;STK192083;AKOS000512692;AC-7643;NCGC00245055-01;LS-60806;SMR000286249;CS-0329516;FT-0659412;AG-690/11629173;W-109649;Q27264131;AMITRIPTYLINE HYDROCHLORIDE IMPURITY D [EP IMPURITY];NORTRIPTYLINE HYDROCHLORIDE IMPURITY D [EP IMPURITY];5-(3-Dimethylaminopropyl)-10,11-2Hdibenzo[a,d]cyclohepten-5-ol;11-[3-(dimethylamino)propyl]-5,6-dihydrodibenzo[1,2-a:1\',2\'-e][7]annulen-11-ol;5-(3-(DIMETHYLAMINO)PROPYL)-10,11-DIHYDRO-5H-DIBENZO(A,D)-CYCLOHEPTEN-5-OL;5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo-[a,d]cyclohepten-5-ol;5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol #;2-[3-(dimethylamino)propyl]tricyclo[9.4.0.0^{3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ol

Chemical Property of Amitriptynol

Chemical Property:

• Vapor Pressure: 1.46E-07mmHg at 25°C
• Melting Point: 119-120℃
• Refractive Index: 1.583
• Boiling Point: 413 °C at 760 mmHg
• PKA: 13.52±0.20(Predicted)
• Flash Point: 186.4 °C
• PSA: 23.47000
• Density: 1.079 g/cm³
• LogP: 3.36290
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 295.193614421
• Heavy Atom Count: 22
• Complexity: 330

Purity/Quality:

98% ^*data from raw suppliers

5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCC1(C2=CC=CC=C2CCC3=CC=CC=C31)O
• Uses: 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol (Amitriptyline EP Impurity D) is an impurity of Amitriptyline (A633350), an antidepressant drug. Amitriptyline (A633350) impurity, an antidepressant drug.

Technology Process of Amitriptynol

There total 5 articles about Amitriptynol 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: 80.0%

3-(N,N-dimethylamino)propylmagnesium chloride (19070-16-7) + 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one (1210-35-1) → 5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol (1159-03-1)

Guidance literature:

With methanol; In tetrahydrofuran; toluene; at 20 ℃; Temperature; Solvent; Flow reactor;

DOI:10.1002/adsc.201300614

Reference yield: 68.0%

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one (1210-35-1) + 3-(Dimethylamino)propyl chloride (109-54-6) → 5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol (1159-03-1)

Guidance literature:

3-(Dimethylamino)propyl chloride; With iodine; magnesium; In tetrahydrofuran; Heating;

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one; In tetrahydrofuran; at 0 - 20 ℃; Further stages.;

DOI:10.1016/j.bmc.2006.09.010

Reference yield:

1-Bromo-2-bromomethyl-benzene (3433-80-5) → 5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol (1159-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium; carbon dioxide / tetrahydrofuran; hexane / -50 - 20 °C / 3878.71 Torr / Flow reactor

2: methanol / tetrahydrofuran; toluene / 20 °C / Flow reactor

With methanol; n-butyllithium; carbon dioxide; In tetrahydrofuran; hexane; toluene; 2: |Grignard Reaction;

DOI:10.1002/adsc.201300614

upstream raw materials:

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

3-(Dimethylamino)propyl chloride

1-Bromo-2-bromomethyl-benzene

3-(N,N-dimethylamino)propylmagnesium chloride

Downstream raw materials:

amitryptyline

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

amitriptyline hydrochloride

5-<3-(N-Carbethoxy-N-methyl-amino>-propyl>-10,11-dihydro-dibenzocyclohepten-5-ol

Refernces

• 1、 Kupracz, Lukas,Kirschning, Andreas. "Multiple organolithium generation in the continuous flow synthesis of amitriptyline". . p. 3375 - 3380. Retrieved 2013/12/04.
• 2、 -. "Benzo-cyclitolamines". . . Retrieved 2008/06/13.