Venlafaxine hydrochloride

Base Information

• Chemical Name: Venlafaxine hydrochloride
• CAS No.: 99300-78-4
• Molecular Formula: C17H28ClNO2
• Molecular Weight: 313.868
• Hs Code.: 29225090
• European Community (EC) Number: 619-421-1
• NSC Number: 745751
• UNII: 7D7RX5A8MO
• DSSTox Substance ID: DTXSID8047397
• Wikidata: Q27108525
• NCI Thesaurus Code: C29540
• RXCUI: 235988
• Pharos Ligand ID: J2GNZM7F1836
• ChEMBL ID: CHEMBL1201066
• Mol file: 99300-78-4.mol

Synonyms:1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol HCl;Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride;Dobupal;Efexor;Effexor;Hydrochloride, Venlafaxine;Sila Venlafaxine;sila-venlafaxine;Trevilor;Vandral;venlafaxine;venlafaxine hydrochloride;Wy 45,030;Wy 45030;Wy-45,030;Wy-45030;Wy45,030;Wy45030

Chemical Property of Venlafaxine hydrochloride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 207-209 °C
• Boiling Point: 397.6 °C at 760 mmHg
• Flash Point: 194.2 °C
• PSA: 32.70000
• Density: 1.394 g/cm3
• LogP: 3.83760
• Storage Temp.: Store at RT
• Solubility.: H2O: >10mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 313.1808568
• Heavy Atom Count: 21
• Complexity: 279

Purity/Quality:

99% ^*data from raw suppliers

Venlafaxine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-36-39/23/24/25-23/24/25-11
• Safety Statements: 26-37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC(C1=CC=C(C=C1)OC)C2(CCCCC2)O.Cl
• Recent ClinicalTrials: Comparative Effectiveness Research Trial for Antidepressant Incomplete and Non-responders With TRD
• Recent EU Clinical Trials: Quinidine versus verapamil in short-coupled idiopathic ventricular fibrillation: An open label, randomized crossover pilot trial
• Description: Venlafaxine hydrochloride, a novel phenethylamine derivative, was introduced in the U.S.A. as an antidepressant. Venlafaxine is reported to be the first in the class of the second-generation of antidepressants with dual serotonidnorepinephrine reuptake inhibitory activity. Venlafaxine lacks any affinity for muscarinic, cholinergic, histaminergic and noradrenergic receptors and therefore, has an unusually favorable side effect profile compared with classical tricyclic antidepressants and shows less cardiotoxicity. In addition, venlafaxine has a rapid onset of action that makes it unique among the antidepressant agents. Other indications for venlafaxine include the treatment of obsessive and panic disorders, and obesity. Both enantiomers of venlafaxine were reported to have similar biological activity.
• Uses: A selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant Venlafaxine hydrochloride is an inhibitor of reuptake of both serotonin (IC50 = 0.21 μM) and norepinephrine (IC50 = 0.64 μM). It is effective in vitro and in vivo and against human as well as rat receptors. As an antidepressant, it is properly placed in the serotonin-norepinephrine reuptake inhibitor class.[Cayman Chemical] An inhibitor of ST and SLC6A2.

Technology Process of Venlafaxine hydrochloride

There total 15 articles about Venlafaxine hydrochloride 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: 95.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) → venlafaxine hydrochloride (99300-78-4)

Guidance literature:

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride; With sodium hydroxide; In methanol; at 0 - 5 ℃; for 0.5h; pH=9 - 9.5;

formaldehyd; With formic acid; In water; at 20 - 100 ℃; for 14 - 15h;

With hydrogenchloride; sodium hydroxide; more than 3 stages;

Reference yield: 95.0%

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol (93413-69-5) → venlafaxine hydrochloride (99300-78-4)

Guidance literature:

With hydrogenchloride; In ethanol; ethyl acetate; at 68 - 73 ℃; pH=2.5;

Reference yield: 94.2%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hemisulfate → venlafaxine hydrochloride (99300-78-4)

Guidance literature:

With hydrogenchloride; formic acid; In dichloromethane; water; pH=1; Reflux;

upstream raw materials:

formaldehyd

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride

N,N-didesmethylvenlafaxine

Downstream raw materials:

1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol

desvenlafaxine succinate

C₁₇H₂₇NO₂*C₂₀H₁₈O₈

2C₁₇H₂₇NO₂*C₂₀H₁₈O₈

Refernces

• 1、 -. "Synthetic method of venlafaxine hydrochloride intermediate". Paragraph 0023-0024; 0026; 0028; 0030; 0032; 0034. . Retrieved 2021/06/02.
• 2、 -. "A method for the preparation of venlafaxine hydrochloride (by machine translation)". . . Retrieved 2017/07/19.