Demexiptiline

Last updated
Demexiptiline
Demexiptiline.png
Demexiptiline-3D-spacefill.png
Clinical data
Trade names Deparon, Tinoran
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life 35 hours [1]
Identifiers
  • 5H-dibenzo(a,d)cyclohepten-5-one O-(2-(methylamino)ethyl)oxime
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H18N2O
Molar mass 278.355 g·mol−1
3D model (JSmol)
  • O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC

Demexiptiline (brand names Deparon, Tinoran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression. [2] [3] It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine. [4]

Contents

Synthesis

The synthesis is similar to that reported for Noxiptiline but also differs in a couple of respects.

Synthesis: Patents: Demexiptiline synthesis.svg
Synthesis: Patents:

The condensation between Dibenzosuberenone [2222-33-5] (1) and hydroxylamine (2) gives the oxime, [1021-91-6] (3). Base catalyzed attachment of the sidechain by reaction with 2-Chloro-N-Methylethanamine [32315-92-7] (4) completed the synthesis of demexiptiline (5).

Related Research Articles

<span class="mw-page-title-main">Tricyclic antidepressant</span> Class of medications

Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants, which is important for the management of depression. They are second-line drugs next to SSRIs. TCAs were discovered in the early 1950s and were marketed later in the decade. They are named after their chemical structure, which contains three rings of atoms. Tetracyclic antidepressants (TeCAs), which contain four rings of atoms, are a closely related group of antidepressant compounds.

<span class="mw-page-title-main">Maprotiline</span> Antidepressant

Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. In terms of its chemistry and pharmacology, maprotiline is closely related to other secondary amine TCAs like nortriptyline and protriptyline, and has similar effects to them.

<span class="mw-page-title-main">Imipramine</span> Antidepressant

Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. The drug is also used to treat bedwetting. Imipramine is taken by mouth.

<span class="mw-page-title-main">Nortriptyline</span> Antidepressant medication

Nortriptyline, sold under the brand name Pamelor, among others, is a medication used to treat depression. This medicine is used for: neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. As with many antidepressants, its use for young people with depression and other psychiatric disorders may be limited due to increased suicidality in the 18-24 population initiating treatment. Nortriptyline is a less preferred treatment for ADHD and stopping smoking. It is taken by mouth.

<span class="mw-page-title-main">Nomifensine</span> Group of stereoisomers

Nomifensine is a norepinephrine-dopamine reuptake inhibitor, i.e. a drug that increases the amount of synaptic norepinephrine and dopamine available to receptors by blocking the dopamine and norepinephrine reuptake transporters. This is a mechanism of action shared by some recreational drugs like cocaine and the medication tametraline. Research showed that the (S)-isomer is responsible for activity.

<span class="mw-page-title-main">Dibenzepin</span> Chemical compound

Dibenzepin, sold under the brand name Noveril among others, is a tricyclic antidepressant (TCA) used widely throughout Europe for the treatment of depression. It has similar efficacy and effects relative to other TCAs like imipramine but with fewer side effects.

<span class="mw-page-title-main">Butriptyline</span> Pharmaceutical drug

Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed. Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

<span class="mw-page-title-main">Lofepramine</span> Chemical compound

Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.

<span class="mw-page-title-main">Melitracen</span> Chemical compound

Melitracen is a tricyclic antidepressant (TCA), for the treatment of depression and anxiety. In addition to single drug preparations, it is also available as Deanxit, marketed by Lundbeck, a combination product containing both melitracen and flupentixol.

<span class="mw-page-title-main">Carpipramine</span> Chemical compound

Carpipramine is an atypical antipsychotic used for the treatment of schizophrenia and anxiety in France and Japan. In addition to its neuroleptic and anxiolytic effects, carpipramine also has hypnotic properties. It is structurally related to both tricyclics like imipramine and butyrophenones like haloperidol.

<span class="mw-page-title-main">Bifemelane</span>

Bifemelane (INN), or bifemelane hydrochloride (JAN), also known as 4-(O-benzylphenoxy)-N-methylbutylamine, is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma. Bifemelane acts as a monoamine oxidase inhibitor (MAOI) of both isoenzymes, with competitive (reversible) inhibition of MAO-A and non-competitive (irreversible) inhibition of MAO-B, and also acts (weakly) as a norepinephrine reuptake inhibitor. The drug has nootropic, neuroprotective, and antidepressant-like effects in animal models, and appears to enhance the cholinergic system in the brain.

<span class="mw-page-title-main">Oxaflozane</span> Chemical compound

Oxaflozane (INN) is an antidepressant and anxiolytic drug that was introduced by Solvay in France in 1982 for the treatment of depression but has since been discontinued. It is a prodrug of flumexadol, which is reported to act as an agonist of the serotonin 5-HT1A and 5-HT2C receptors and, to a much lesser extent, of the 5-HT2A receptor. In addition to its serotonergic properties, oxaflozane may also produce anticholinergic side effects at high doses, namely in overdose.

<span class="mw-page-title-main">Quinupramine</span>

Quinupramine is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.

<span class="mw-page-title-main">Noxiptiline</span>

Noxiptiline, also known as noxiptyline and dibenzoxine, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1970s for the treatment of depression. It has imipramine-like effects, acting as a serotonin and norepinephrine reuptake inhibitor, among other properties. Of the TCAs, noxiptiline has been described as one of the most effective, rivaling amitriptyline in clinical efficacy.

<span class="mw-page-title-main">Amitriptylinoxide</span> Chemical compound

Amitriptylinoxide, or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.

<span class="mw-page-title-main">Imipraminoxide</span>

Imipraminoxide, or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.

<span class="mw-page-title-main">Propizepine</span>

Propizepine is a tricyclic antidepressant (TCA) used in France for the treatment of depression which was introduced in the 1970s.

<span class="mw-page-title-main">Pipofezine</span>

Pipofezine, sold under the brand name Azafen or Azaphen, is an antidepressant approved in Russia for the treatment of depression. It was introduced in the late 1960s and is still used today.

<span class="mw-page-title-main">Fluotracen</span> Chemical compound

Fluotracen (SKF-28,175) is a tricyclic drug which possesses dual antidepressant and antipsychotic activity. This profile of effects is similar to that of related agents like amoxapine, loxapine, and trimipramine which may also be used in the treatment of both depression and psychosis. It was believed that such duality would be advantageous in the treatment of schizophrenia, as depression is often comorbid with the disorder and usual antipsychotics often worsen such symptoms. In any case, however, fluotracen was never marketed.

<span class="mw-page-title-main">Litracen</span>

Litracen (N-7,049) is a tricyclic antidepressant which was never marketed.

References

  1. Florencio Zaragoza Dörwald (4 February 2013). Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds. John Wiley & Sons. pp. 313–. ISBN   978-3-527-64565-7.
  2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 301. ISBN   3-88763-075-0.
  3. David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 583. ISBN   0-412-46630-9.
  4. Teste JF, Pelsy-Johann I, Decelle T, Boulu RG (1993). "Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice". Fundamental & Clinical Pharmacology. 7 (5): 219–26. doi:10.1111/j.1472-8206.1993.tb00235.x. PMID   8370568. S2CID   24240307.
  5. Aichinger G, Behner O, Hoffmeister F, Schütz S. Basische tricyclische Oxyiminoäther und ihre pharmakologischen Eigenschaften [Basic tricyclic oxyiminoethers and their pharmacological properties]. Arzneimittelforschung. 1969 Jun;19:Suppl 5a:838+. German. PMID: 5819763.
  6. Siegismund Schutz, Otto Behner, & Friedrich Hoffmeister, U.S. Patent 3,989,844 & U.S. Patent 3,963,778 (both 1976 to Bayer AG).
  7. Dr Sigismund Schuetz, Dr Otto Behner, Dr Friedrich Hoffmeister, DE 1247302 (1967 to Bayer Ag).

Further reading