3,4-Dichloroamphetamine
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3,4-Dichloroamphetamine (3,4-DCA), is an
amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...
derived
drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...
invented by
Eli Lilly Eli Lilly (July 8, 1838 – June 6, 1898) was a Union Army officer, pharmacist, chemist, and businessman who founded Eli Lilly and Company. Lilly enlisted in the Union Army during the American Civil War and recruited a company of men to ...
in the 1960s, which has a number of pharmacological actions. It acts as a highly potent and 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 ...
(SSRA) and binds to the
serotonin transporter The serotonin transporter (SERT or 5-HTT) also known as the sodium-dependent serotonin transporter and solute carrier family 6 member 4 is a protein that in humans is encoded by the SLC6A4 gene. SERT is a type of monoamine transporter protein t ...
with high
affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...
, but also acts as a selective
serotonergic neurotoxin A monoamine neurotoxin, or monoaminergic neurotoxin, is a drug that selectively damages or destroys monoaminergic neurons. Monoaminergic neurons are neurons that signal via stimulation by monoamine neurotransmitters including serotonin, dopamine ...
in a similar manner to the related ''para''-chloroamphetamine (PCA), though with slightly lower potency. It is also a
monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, 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 antidepressa ...
(MAOI), as well as a very potent
inhibitor Inhibitor or inhibition may refer to: Biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotransmi ...
of the enzyme phenylethanolamine ''N''-methyl transferase which normally functions to transform
noradrenaline Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as a hormone, neurotransmitter and neuromodulator. The name "noradrenaline" (from ...
into
adrenaline Adrenaline, also known as epinephrine, is a hormone and medication which is involved in regulating visceral functions (e.g., respiration). It appears as a white microcrystalline granule. Adrenaline is normally produced by the adrenal glands a ...
in the body.


Chemistry


Synthesis

The reaction of 3,4-dichlorobenzyl chloride (1) with cyanide anion gives 3,4-dichlorophenylacetonitrile (2). Reaction with sodium methoxide and
ethyl acetate Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, ...
gives α-acetoxy-3,4-dichlorophenylacetonitrile, (3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-dichlorophenylacetone (4). Oxime formation with hydroxylamine gives N- -(3,4-dichlorophenyl)propan-2-ylideneydroxylamine, (5). Reduction of the oxime completed the synthesis of 3,4-dichloroamphetamine (6).


See also

*
2,4-Dichloroamphetamine 2,4-Dichloroamphetamine (2,4-DCA) is a psychostimulant of the amphetamine family and a potent serotonergic neurotoxin related to ''para''-chloroamphetamine (PCA; 4-chloroamphetamine). It is also a potent monoamine oxidase inhibitor Monoa ...
* 3-Chloroamphetamine *
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. MMA was largely forgotte ...
* Cendifensine * Cericlamine *
Chlorphentermine Chlorphentermine, sold under the brand names Apsedon, Desopimon, and Lucofen, is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the ''para''- chloro derivative of the better-known appetite suppressant ph ...
* Clortermine * Etolorex * 3,4-Methylenedioxyamphetamine * ''para''-Chloroamphetamine * ''para''-Methoxyamphetamine


References

{{DEFAULTSORT:Dichloroamphetamine, 3,4- Abandoned drugs Monoamine oxidase inhibitors Monoaminergic neurotoxins Serotonin-norepinephrine-dopamine releasing agents Serotonin releasing agents Substituted amphetamines