Para-Ethoxyamphetamine

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para-Ethoxyamphetamine
4-EtOamph.png
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Legal status
Identifiers
  • 1-(4-ethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
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UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H17NO
Molar mass 179.263 g·mol−1
3D model (JSmol)
  • O(c1ccc(cc1)CC(N)C)CC
  • InChI=1S/C11H17NO/c1-3-13-11-6-4-10(5-7-11)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3 Yes check.svgY
  • Key:CCAMEVFYMFXHEN-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

para-Ethoxyamphetamine, also known as 4-ethoxyamphetamine (4-ETA), is a psychoactive drug and research chemical of the phenethylamine and amphetamine chemical classes which is closely related to the infamous para-methoxyamphetamine (PMA). para-Ethoxyamphetamine has similar effects to PMA in animal studies, although with slightly weaker stimulant effects. [1] [2] [3] Like PMA, it has prominent MAOI activity, [4] and is likely to have similar dangers associated with its use.

See also

Related Research Articles

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<span class="mw-page-title-main">Phenethylamine</span> Organic compound, a stimulant in humans

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

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<i>para</i>-Methoxy-<i>N</i>-methylamphetamine Group of stereoisomers

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MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in vitro and produces entactogen effects in humans.

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<span class="mw-page-title-main">3-Methoxyamphetamine</span> Chemical compound

meta-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA), although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA. 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer. It produces gepefrine, a cardiac stimulant, as one of its major metabolites.

<span class="mw-page-title-main">3-Methoxymethamphetamine</span> Chemical compound

3-Methoxymethamphetamine, which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extensively as other related drugs. It is an agonist of human TAAR1.

<span class="mw-page-title-main">2-Methoxyamphetamine</span>

2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine class. It is substantially weaker in inhibiting the reuptake of and inducing the release of the monoamine neurotransmitters compared to related agents such as amphetamine, MMA, and PMA, and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine.

A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamine transporters (MATs), which include the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT). This in turn results in an increase in the synaptic concentrations of one or more of these neurotransmitters and therefore an increase in monoaminergic neurotransmission.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">4-Methylcathinone</span> Chemical compound

4-Methylcathinone, is a stimulant drug of the cathinone chemical class that has been sold online as a designer drug. It is a metabolite of the better known drug mephedrone (4-methylmethcathinone).

<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.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

References

  1. Martin-Iverson MT, Yamada N, By AW, Lodge BA (December 1991). ""Designer" amphetamines: effects on behavior and monoamines with or without reserpine and/or alpha-methyl-para-tyrosine pretreatment". Journal of Psychiatry & Neuroscience. 16 (5): 253–61. PMC   1188362 . PMID   1686728.
  2. Corrigall WA, Robertson JM, Coen KM, Lodge BA (January 1992). "The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine". Pharmacology Biochemistry and Behavior. 41 (1): 165–9. CiteSeerX   10.1.1.670.6929 . doi:10.1016/0091-3057(92)90077-S. PMID   1539067. S2CID   30080516.
  3. Hegadoren KM, Greenshaw AJ, Baker GB, Martin-Iverson MT, Lodge B, Soin S (January 1994). "4-Ethoxyamphetamine: effects on intracranial self-stimulation and in vitro uptake and release of 3H-dopamine and 3H-serotonin in the brains of rats". Journal of Psychiatry & Neuroscience. 19 (1): 57–62. PMC   1188563 . PMID   8148367.
  4. Martin-Iverson MT, Lodge BA (December 1991). "Effects of chronic treatment of rats with "designer" amphetamines on brain regional monoamines". Canadian Journal of Physiology and Pharmacology. 69 (12): 1825–32. doi:10.1139/y91-270. PMID   1802356.