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 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. ...

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 A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter e ...

) that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and

anorexia nervosa Anorexia nervosa, often referred to simply as anorexia, is an eating disorder characterized by low weight, food restriction, body image disturbance, fear of gaining weight, and an overpowering desire to be thin. ''Anorexia'' is a term of Gr ...

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 participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, diet ...

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 indu ...

with a diazonium salt of

3,4-dichloroaniline Dichloroanilines are chemical compounds which consist of an aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an indust ...

(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.

References

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

Synthesis

See also

References