2,4-Dichloroamphetamine

Last updated

2,4-Dichloroamphetamine
2,4-Dichloroamphetamine.svg
Clinical data
Other names2,4-DCA
Drug class Psychostimulant; Serotonergic neurotoxin; Monoamine oxidase inhibitor
Identifiers
  • 1-(2,4-dichlorophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C9H11Cl2N
Molar mass 204.09 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=C(C=C1)Cl)Cl)N
  • InChI=1S/C9H11Cl2N/c1-6(12)4-7-2-3-8(10)5-9(7)11/h2-3,5-6H,4,12H2,1H3
  • Key:WFXOKSCQUWGEEH-UHFFFAOYSA-N

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). [1] [2] It is also a potent monoamine oxidase inhibitor. [1] [3] [2]

See also

Related Research Articles

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">4-Fluoroamphetamine</span> Psychoactive research chemical

4-Fluoroamphetamine, also known as para-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.

<span class="mw-page-title-main">Chlorphentermine</span> Weight loss medication

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 phentermine, which is still in current use.

<span class="mw-page-title-main">Norfenfluramine</span> Never-marketed drug of the amphetamine family

Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family and a major active metabolite of the appetite suppressants fenfluramine and benfluorex. The compound is a racemic mixture of two enantiomers with differing activities, dexnorfenfluramine and levonorfenfluramine.

<i>para</i>-Chloroamphetamine Chemical compound

para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonergic neurotoxin of the amphetamine family. It is used in scientific research in the study of the serotonin system, as a serotonin releasing agent (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin.

<span class="mw-page-title-main">MDAI</span> Chemical compound

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen drug of the 2-aminoindane group which is related to MDMA and produces similar subjective effects.

<span class="mw-page-title-main">3-Methoxy-4-methylamphetamine</span> Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

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 forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.

<span class="mw-page-title-main">Serotonin releasing agent</span> Class of compounds

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 efflux at other types of monoamine neurons, including dopamine and norepinephrine neurons.

Phenylpropylamine, also known as 3-phenylpropylamine, is a monoamine releasing agent (MRA) related to phenethylamine (2-phenylethylamine). It is the analogue of phenethylamine in which the ethylamine side chain has been lengthened by one carbon atom to instead be a propylamine chain.

<span class="mw-page-title-main">4-Methylamphetamine</span> Stimulant and anorectic drug of the amphetamine class

4-Methylamphetamine is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes.

α-Methyldopamine Chemical compound

α-Methyldopamine (α-Me-DA), also known as 3,4-dihydroxyamphetamine or as catecholamphetamine, is a research chemical of the catecholamine and amphetamine families. It is a monoamine releasing agent and a metabolite of MDMA and MDA. The bis-glutathionyl metabolite of α-methyldopamine is slightly neurotoxic when directly injected into the brain's ventricles.

<span class="mw-page-title-main">3,4-Dichloromethylphenidate</span> Stimulant drug

3,4-dichloromethylphenidate is a potent stimulant drug from the phenidate class closely related to methylphenidate. It acts as a potent serotonin-norepinephrine-dopamine reuptake inhibitor with a long duration of action. It has been sold online as a designer drug.

<span class="mw-page-title-main">4-Chlorophenylisobutylamine</span> Entactogen and stimulant drug of the phenethylamine class

4-Chlorophenylisobutylamine, also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is an analogue of para-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.

<span class="mw-page-title-main">3,4-Dichloroamphetamine</span> Chemical compound

3,4-Dichloroamphetamine (3,4-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 serotonin transporter with high affinity, but also acts as a selective serotonergic neurotoxin in a similar manner to the related para-chloroamphetamine, though with slightly lower potency. It is also a monoamine oxidase inhibitor (MAOI), as well as a very potent inhibitor of the enzyme phenylethanolamine N-methyl transferase which normally functions to transform noradrenaline into adrenaline in the body.

<i>para</i>-Chloromethamphetamine Chemical compound

para-Chloromethamphetamine is a stimulant that is the N-methyl derivative and prodrug of the neurotoxic drug para-chloroamphetamine (4-CA). It has been found to decrease serotonin in rats. Further investigation into the long-term effects of chloroamphetamines discovered that administration of 4-CMA caused a prolonged reduction in the levels of serotonin and the activity of tryptophan hydroxylase in the brain one month after injection of a single dose of the drug.

<span class="mw-page-title-main">Cericlamine</span> Chemical compound

Cericlamine is a potent and moderately selective serotonin reuptake inhibitor (SSRI) of the amphetamine family that was investigated as an antidepressant for the treatment of depression, anxiety disorders, and anorexia nervosa by Jouveinal but did not complete development and was never marketed. It reached phase III clinical trials in 1996 before development was discontinued in 1999.

<span class="mw-page-title-main">Monoamine neurotoxin</span> Compounds that damage or destroy monoaminergic neurons

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, and norepinephrine.

<span class="mw-page-title-main">3-Chloroamphetamine</span> Serotonergic neurotoxin

3-Chloroamphetamine (3-CA), also known as meta-chloroamphetamine, is a psychostimulant of the amphetamine family and a potent serotonergic neurotoxin related to para-chloroamphetamine (PCA). It is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).

<span class="mw-page-title-main">2-Chloroamphetamine</span> Pharmaceutical compound

2-Chloroamphetamine (2-CA), also known as ortho-chloroamphetamine (OCA), is a monoamine releasing agent (MRA) of the amphetamine family related to 2-fluoroamphetamine (2-FA).

<i>para</i>-Bromomethamphetamine Pharmaceutical compound

para-Bromomethamphetamine, also known as 4-bromomethamphetamine (4-BMA), is a monoaminergic drug of the amphetamine family related to para-chloroamphetamine. It was studied by József Knoll and colleagues in the 1970s and 1980s.

References

  1. 1 2 Biel JH, Bopp BA (1978). "Amphetamines: Structure-Activity Relationships". In Iversen L, Snyder SH, Iversen SD (eds.). Stimulants. Boston, MA: Springer US. p. 1–39. doi:10.1007/978-1-4757-0510-2_1. ISBN   978-1-4757-0512-6.
  2. 1 2 Fuller RW, Snoddy HD, Roush BW, Molloy BB (January 1973). "Further structure-activity studies on the lowering of brain 5-hydroxyindoles by 4-chloramphetamine". Neuropharmacology. 12 (1). Elsevier BV: 33–42. doi:10.1016/0028-3908(73)90129-9. PMID   4687274.
  3. ↑ Conde S, Madroñero R, Fernández-Tomé MP, del Río J (September 1978). "Effects of thiophene analogues of chloroamphetamines on central serotonergic mechanisms". Journal of Medicinal Chemistry. 21 (9). American Chemical Society (ACS): 978–981. doi:10.1021/jm00207a024. PMID   722762.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.