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. F ...
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
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
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, hea ...
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 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, dietar ...
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 (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 and Company, Eli Lilly in the 1960s, which has a number of pharmacological actions. It acts as a highly potent and binding selectivity, selective selective seroto ...
*
Alaproclate
Alaproclate (developmental code name GEA-654) is a drug that was being developed as an antidepressant by the Swedish pharmaceutical company Astra AB (now AstraZeneca) in the 1970s. It acts as a selective serotonin reuptake inhibitor (SSRI), and ...
*
Bupropion
*
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
Clortermine (Voranil) was developed by Ciba in the 1960s and is an anorectic drug of the amphetamine class. It is the 2-chloro analogue of the better known appetite suppressant phentermine, and is the 2-chloro positional isomer of chlorphenter ...
*
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
* Me ...
*
Femoxetine
Femoxetine (INN; tentative brand name Malexil; developmental code name FG-4963) is a drug related to paroxetine that was being developed as an antidepressant by Danish pharmaceutical company Ferrosan in 1975 before acquisition of the company by ...
*
Ifoxetine
Ifoxetine (CGP-15,210-G) is a selective serotonin reuptake inhibitor (SSRI) which was investigated as an antidepressant in the 1980s but was never marketed. Ifoxetine selectively blocks the reuptake of serotonin in the brain supposedly without ...
*
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 s ...
*
Methylenedioxyphentermine
3,4-Methylenedioxyphentermine (MDPH) is a lesser-known psychedelic drug. MDPH was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', the dosage range is listed as 160–240 mg, and the ...
*
Omiloxetine
Omiloxetine (omiloextinum, omiloxetino INN) was a 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 diso ...
*
Panuramine
Panuramine (Wy-26,002) is an antidepressant which was synthesized in 1981 by Wyeth. It acts as a potent and selective serotonin reuptake inhibitor (SSRI). It was never marketed.
See also
* Selective serotonin reuptake inhibitor
Selecti ...
*
''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
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI). It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed. ...
*
Seproxetine
Seproxetine, also known as (''S'')-norfluoxetine, is a selective serotonin reuptake inhibitor (SSRI). It is the ''S'' enantiomer of norfluoxetine, the main active metabolite of the widely used antidepressant fluoxetine; but little is known ...
*
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 d ...
*
Zimelidine
Zimelidine (INN, BAN) (brand names Zimeldine, Normud, Zelmid) was one of the first selective serotonin reuptake inhibitor (SSRI) antidepressants to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants ...
References
{{Phenethylamines
Dimethylamino compounds
Antidepressants
Chlorobenzenes
Phenethylamines
Selective serotonin reuptake inhibitors
Substituted amphetamines