Nortriptyline

Base Information

• Chemical Name: Nortriptyline
• CAS No.: 72-69-5
• Molecular Formula: C19H21N
• Molecular Weight: 263.382
• Hs Code.: 2921499090
• European Community (EC) Number: 200-788-8
• NSC Number: 757234
• UNII: BL03SY4LXB
• DSSTox Substance ID: DTXSID9023384
• Nikkaji Number: J5.253A
• Wikipedia: Nortriptyline
• Wikidata: Q61387
• NCI Thesaurus Code: C62060
• RXCUI: 7531
• Pharos Ligand ID: DK46VHLBQ3MP
• Metabolomics Workbench ID: 42877
• ChEMBL ID: CHEMBL445
• Mol file: 72-69-5.mol

Synonyms:Allegron;Apo Nortriptyline;Apo-Nortriptyline;Aventyl;Desitriptyline;Desmethylamitriptylin;Gen Nortriptyline;Gen-Nortriptyline;Hydrochloride, Nortriptyline;Norfenazin;Nortrilen;Nortriptyline;Nortriptyline Hydrochloride;Novo Nortriptyline;Novo-Nortriptyline;Nu Nortriptyline;Nu-Nortriptyline;Pamelor;Paxtibi;PMS Nortriptyline;PMS-Nortriptyline;ratio Nortriptyline;ratio-Nortriptyline

Chemical Property of Nortriptyline

Chemical Property:

• Vapor Pressure: 1.02E-06mmHg at 25°C
• Melting Point: 58 °C
• Refractive Index: 1.633
• Boiling Point: 403.4 °C at 760 mmHg
• PKA: pKa 9.7 (Uncertain)
• Flash Point: 194.9 °C
• PSA: 12.03000
• Density: 1.084 g/cm³
• LogP: 4.21730
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 263.167399674
• Heavy Atom Count: 20
• Complexity: 307

Purity/Quality:

99%, ^*data from raw suppliers

Nortriptyline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: CNCCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
• Recent ClinicalTrials: Antidepressants Trial in Parkinson's Disease
• Recent EU Clinical Trials: A Randomised Controlled Trial of Escitalopram and Nortriptyline compared with placebo and standard psychological care for depression in Parkinson’s Disease
• Uses: Nortriptyline is a drug with a relatively short latent period of action. It is practically devoid of sedative effects. It is used in manic-depressive psychoses, in all forms of endogenous depression, and also in major depressive conditions. Antidepressant.
• Therapeutic Function: Antidepressant
• Clinical Use: Tricyclic antidepressant
• Drug interactions: Potentially hazardous interactions with other drugs Alcohol: increased sedative effect. Analgesics: increased risk of CNS toxicity with tramadol; possibly increased risk of side effects with nefopam; possibly increased sedative effects with opioids. Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; increased risk of ventricular arrhythmias with disopyramide, flecainide or propafenone; avoid with dronedarone. Antibacterials: increased risk of ventricular arrhythmias with delamanid, moxifloxacin and possibly telithromycin - avoid with moxifloxacin. Anticoagulants: may alter anticoagulant effect of coumarins. Antidepressants: enhanced CNS excitation and hypertension with MAOIs and moclobemide - avoid; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; increased risk of convulsions with vortioxetine. Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, fosphenytoin, phenobarbital and possibly phenytoin. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, haloperidol, pimozide, risperidone and sulpiride - avoid; increased antimuscarinic effects with clozapine and phenothiazines; concentration increased by antipsychotics. Antivirals: increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased with ritonavir. Atomoxetine: increased risk of ventricular arrhythmias and possibly convulsions. Beta-blockers: increased risk of ventricular arrhythmias with sotalol. Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal. Dapoxetine: possible increased risk of serotonergic effects - avoid. Dopaminergics: avoid use with entacapone; CNS toxicity reported with selegiline and rasagiline. Pentamidine: increased risk of ventricular arrhythmias. Sympathomimetics: increased risk of hypertension and arrhythmias with adrenaline and noradrenaline; metabolism possibly inhibited by methylphenidate.

Technology Process of Nortriptyline

There total 33 articles about Nortriptyline 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: 69.0%

amitriptyline hydrochloride (549-18-8,8058-15-9) → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5) + 10-Hydroxynortriptyline (1156-99-6) + (Z)-10-Hydroxyamitriptyline (64520-05-4)

Guidance literature:

With glucose dehydrogenase; D-glucose; cytochrome P_450BM3 F₈₇A/H₁₇₁L/Q₃₀₇H/N₃₁₉Y mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt; In ethanol; at 25 ℃; for 2h; pH=8.5; Enzymatic reaction;

DOI:10.1002/chem.201502020

Reference yield: 68.0%

N-methyl-4-(2-phenethylphenyl)but-3-yn-1-amine → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.166667h; regioselective reaction;

DOI:10.1039/c5cc01257k

Reference yield:

Desmethylnortriptyline (4444-42-2) + methyl iodide (74-88-4) → 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine (72-69-5)

Guidance literature:

Desmethylnortriptyline; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.333333h;

methyl iodide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 4h;

upstream raw materials:

5-<3-(N-Carbethoxy-N-methyl-amino)-propyliden>-10,11-dihydro-dibenzocyclohepten

5-<3-(N-Methyl-p-toluolsulfonamido)-propyliden>-10,11-dihydro-dibenzocyclohepten

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

5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Downstream raw materials:

Desmethylnortriptyline

(+)-(Z)-10-Hydroxy-Nortriptyline

(E)-10-Hydroxynortriptyline

N-[6-O-trityl-β-D-glucopyranosyl]-N-methyl-3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propanamine

Refernces

• 1、 Bajda, Marek,Filipek, Barbara,Kotniewicz, Krzysztof,Kulig, Katarzyna,Latacz, Gniewomir,Maj, Maciej,Malawska, Barbara,Podkowa, Adrian,Rapacz, Anna,Wanner, Klaus T.,??tka, Kamil,H?fner, Georg C.,Jó?wiak, Krzysztof,Sa?at, Kinga,Zar?ba, Paula. "Development of tricyclic N-benzyl-4-hydroxybutanamide derivatives as inhibitors of GABA transporters mGAT1-4 with anticonvulsant, antinociceptive, and antidepressant activity". . . Retrieved 2021/05/26.
• 2、 Farnoudian-Habibi, Amir,Massoumi, Bakhshali,Jaymand, Mehdi. "A novel strategy for spectrophotometric simultaneous determination of amitriptyline and nortriptyline based on derivation with a quinonoid compound in serum samples". . p. 235 - 243. Retrieved 2016/07/06.