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Cericlamine (
INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...
; developmental code JO-1017) is a potent and moderately
selective serotonin reuptake inhibitor Selective serotonin reuptake inhibitors (SSRIs) are a class of drugs that are typically used as antidepressants in the treatment of major depressive disorder, anxiety disorders, and other psychological conditions. SSRIs increase the extracellul ...
(SSRI) of the
amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
family (specifically, a
derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...
of
phentermine Phentermine ( phenyl- tertiary-butyl amine), with several brand names including Ionamin and Sentis, is a medication used together with diet and exercise to treat obesity. It is taken by mouth for up to a few weeks at a time, after which the ben ...
, and closely related to
chlorphentermine Chlorphentermine (trade names Apsedon, Desopimon, Lucofen) is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the 4-chloro derivative of the better known appetite suppressant phentermine, which is still in ...
, a highly selective serotonin releasing agent) that was investigated as an
antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness ...
for the treatment of depression,
anxiety disorder Anxiety disorders are a cluster of mental disorders characterized by significant and uncontrollable feelings of anxiety and fear such that a person's social, occupational, and personal function are significantly impaired. Anxiety may cause physi ...
s, and
anorexia nervosa Anorexia nervosa, often referred to simply as anorexia, is an eating disorder characterized by underweight, low weight, Calorie restriction, food restriction, body image disturbance, fear of gaining weight, and an overpowering desire to be thi ...
by Jouveinal but did not complete development and was never marketed. It reached phase III
clinical trial Clinical trials are prospective biomedical or behavioral research studies on human subject research, human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel v ...
s in 1996 before development was discontinued in 1999.


Synthesis

Arylation of
methacrylic acid Methacrylic acid, abbreviated MAA, is an organic compound. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced indus ...
with a diazonium salt of
3,4-dichloroaniline Dichloroanilines are chemical compounds which consist of an aniline ring substituted with two chlorine atoms and have the molecular formula C6H5Cl2N. There are six isomers, varying in the positions of the chlorine atoms around the ring relative to ...
(or 3,4-dichloro-benzenediazonium salt), is carried out according to the Meerwein reaction catalysed by a metallic halide. For the next step, the halide is displaced by dimethylamine, then esterification is performed, followed by reduction with a metal hydride.


See also

*
3,4-Dichloroamphetamine 3,4-Dichloroamphetamine (DCA), is an amphetamine derived drug invented by Eli Lilly in the 1960s, which has a number of pharmacological actions. It acts as a highly potent and selective serotonin releasing agent (SSRA) and binds to the seroto ...
* Alaproclate *
Bupropion Bupropion, sold under the brand names Wellbutrin and Zyban among others, is an atypical antidepressant primarily used to treat major depressive disorder and to support smoking cessation. It is also popular as an add-on medication in the cas ...
*
Chlorphentermine Chlorphentermine (trade names Apsedon, Desopimon, Lucofen) is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the 4-chloro derivative of the better known appetite suppressant phentermine, which is still in ...
* Clortermine * Cloforex *
Etolorex Etolorex is an anorectic of the amphetamine class. It was never marketed. Synthesis Made by the reaction of chlorphentermine with 2-Chloroethanol. See also * 3,4-Dichloroamphetamine * Cericlamine * Chlorphentermine * Cloforex * Clortermine ...
* Femoxetine * Ifoxetine *
Indalpine Indalpine ( INN, BAN; brand name Upstène; developmental code name LM-5008) is a selective serotonin reuptake inhibitor (SSRI) class drug that was briefly marketed. It was discovered in 1977 by the pharmacologists Le Fur and Uzan at Pharmuka, a ...
* Methylenedioxyphentermine * Omiloxetine * Panuramine * ''para''-Chloroamphetamine * ''para''-Chloromethamphetamine *
Phentermine Phentermine ( phenyl- tertiary-butyl amine), with several brand names including Ionamin and Sentis, is a medication used together with diet and exercise to treat obesity. It is taken by mouth for up to a few weeks at a time, after which the ben ...
* Pirandamine * Seproxetine *
Viqualine Viqualine ( INN) (developmental code name PK-5078) is an antidepressant and anxiolytic drug that was never marketed. It acts as a potent and selective serotonin releasing agent and serotonin reuptake inhibitor. In addition, viqualine displaces ...
* Zimelidine


References

{{Phenethylamines Dimethylamino compounds Antidepressants Chlorobenzenes Phenethylamines Selective serotonin reuptake inhibitors Substituted amphetamines