3,4-Dichloroamphetamine on:
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3,4-Dichloroamphetamine (DCA), is an
The reaction of 3,4-Dichlorobenzyl Chloride 02-47-6(1) with cyanide anion gives 3,4-Dichlorophenylacetonitrile 218-49-3(2). Reaction with sodium methoxide and ethylacetate gives Alpha-Acetoxy-3,4-Dichlorobenzeneacetonitrile
CID:14318103
(3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-Dichlorophenylacetone 097-32-1(4). Oxime formation with hydroxylamine gives N- -(3,4-dichlorophenyl)propan-2-ylideneydroxylamine
CID:74315855
(5). Reduction of the oxime completed the synthesis of 3,4-Dichloroamphetamine (6).
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 ...
derived drug
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
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 serotonin transporter with high affinity, but also acts as a selective serotonergic neurotoxin
Neurotoxins are toxins that are destructive to nerve tissue (causing neurotoxicity). Neurotoxins are an extensive class of exogenous chemical neurological insultsSpencer 2000 that can adversely affect function in both developing and mature ner ...
in a similar manner to the related para-chloroamphetamine, though with slightly lower potency. It is also a monoamine oxidase inhibitor
Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, espe ...
(MAOI), as well as a very potent inhibitor of the enzyme phenylethanolamine N-methyl transferase
Phenylethanolamine ''N''-methyltransferase (PNMT) is an enzyme found primarily in the adrenal medulla that converts norepinephrine (noradrenaline) to epinephrine (adrenaline). It is also expressed in small groups of neurons in the human brain and ...
which normally functions to transform noradrenaline into adrenaline in the body.Synthesis
The reaction of 3,4-Dichlorobenzyl Chloride 02-47-6(1) with cyanide anion gives 3,4-Dichlorophenylacetonitrile 218-49-3(2). Reaction with sodium methoxide and ethylacetate gives Alpha-Acetoxy-3,4-DichlorobenzeneacetonitrileCID:14318103
(3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-Dichlorophenylacetone 097-32-1(4). Oxime formation with hydroxylamine gives N- -(3,4-dichlorophenyl)propan-2-ylideneydroxylamine
CID:74315855
(5). Reduction of the oxime completed the synthesis of 3,4-Dichloroamphetamine (6).
See also
*3-Methoxy-4-methylamphetamine
3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade.de Zorzi C, Cavalli A, Un ...
* Cericlamine
* Chlorphentermine
* Clortermine
* Etolorex
* 3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts mo ...
* Parachloroamphetamine
* Paramethoxyamphetamine
References
Monoamine oxidase inhibitors Neurotoxins Serotonin-norepinephrine-dopamine releasing agents Serotonin releasing agents Substituted amphetamines {{Nervous-system-drug-stub