CID 657376

Base Information

• Chemical Name: CID 657376
• CAS No.: 549-18-8
• Molecular Formula: C20H23N.HCl
• Molecular Weight: 313.87
• Hs Code.: 29214990
• Mol file: 549-18-8.mol

Synonyms:AKOS015917367

Chemical Property of CID 657376

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.5E-06mmHg at 25°C
• Melting Point: 196-197 °C
• Boiling Point: 398.2 °C at 760 mmHg
• PKA: 9.4(at 25℃)
• Flash Point: 174 °C
• PSA: 3.24000
• Density: 1.076g/cm3
• LogP: 4.97060
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble
• Water Solubility.: almost transparency
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 313.1597275
• Heavy Atom Count: 22
• Complexity: 331

Purity/Quality:

98% ^*data from raw suppliers

Amitriptyline hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, F
• Hazard Codes: T,F,N,Xn
• Statements: 23/24/25-36/37/38-42/43-63-39/23/24/25-11-50/53-36-22
• Safety Statements: 22-26-36/37/39-45-36/37-16-61-60-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [H+].CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.[Cl-]
• Description: Amitriptyline (hydrochloride) (CRM) (Item No. 19031) is a certified reference material categorized as a tricyclic antidepressant. This product is intended for analytical forensic applications. This product is also available as a general research tool .
• Uses: Amitriptyline hydrochloride is a tricyclic antidepressant drug. Amitriptyline hydrochloride inhibits the norepinephrine and serotonin transporters but has a high affinity for α1-adrenergic, serotonin and muscarinic acetylcholine receptors. Amitriptyline hydrochloride has been used:as an antidepressant to study its effects on social behavior and memory in transgenic for acid sphingomyelinase (t-ASM) miceas a tricyclic antidepressant to analyze its effects on glucocorticoid receptor function in whole human bloodas an anti-depressant to study its effects on scratching and locomotion behavior in chloroquine-induced mouse
• Therapeutic Function: Antidepressant
• Clinical Use: Tricyclic antidepressant: Depression, used especially where sedation is required Neuropathic pain (unlicensed) Migraine prophylaxis (unlicensed)
• 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 moxifloxacin and delamanid - avoid with moxifloxacin. Anticoagulants: may alter anticoagulant effect of coumarins. Antidepressants: possibly increased serotonergic effects with duloxetine; enhanced CNS excitation and hypertension with MAOIs and moclobemide; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine; concentration reduced by St John’s wort. Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, phenobarbital and possibly fosphenytoin, phenytoin and primidone. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, fluphenazine, haloperidol, pimozide, sulpiride and zuclopenthixol - 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. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide. Dapoxetine: possibly increased risk of serotonergic effects - avoid. Dopaminergics: avoid 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 CID 657376

There total 6 articles about CID 657376 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: 63.0%

5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol (1159-03-1) → amitriptyline hydrochloride (549-18-8,8058-15-9)

Guidance literature:

With hydrogenchloride; In ethanol; Heating;

DOI:10.1016/j.bmc.2006.09.010

Reference yield:

amitryptyline (50-48-6) → amitriptyline hydrochloride (549-18-8,8058-15-9)

Guidance literature:

With hydrogenchloride; In isopropyl alcohol; at 20 ℃; Flow reactor;

DOI:10.1002/adsc.201300614

Reference yield:

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one (1210-35-1) → amitriptyline hydrochloride (549-18-8,8058-15-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium; I₂ / tetrahydrofuran / Heating

1.2: 68 percent / tetrahydrofuran / 0 - 20 °C

2.1: 63 percent / aq. HCl / ethanol / Heating

With hydrogenchloride; iodine; magnesium; In tetrahydrofuran; ethanol; 1.2: Grignard reaction;

DOI:10.1016/j.bmc.2006.09.010

upstream raw materials:

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

3-(Dimethylamino)propyl chloride

5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol

amitryptyline

Downstream raw materials:

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

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

Desmethylnortriptyline

(Z)-10-Hydroxyamitriptyline

Refernces

• 1、 Hudgens, Debjani P.,Taylor, Catherine,Batts, Timothy W.,Patel, Manoj K.,Brown, Milton L.. "Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2". . p. 8366 - 8378. Retrieved 2008/02/05.