Ethcathinone

Last updated
Ethcathinone
Ethcathinone.svg
Ethcathinone molecule ball.png
Clinical data
Other namesN-Ethylcathinone; 2-Ethylaminopropiophenone
Routes of
administration 		By mouth, intranasal
ATC code
  • none
Legal status
Legal status
Identifiers
  • (RS)-2-ethylamino-1-phenyl-propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO
Molar mass 177.247 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
Melting point 195 to 198 °C (383 to 388 °F) (hydrochloride)
Boiling point 272.3 °C (522.1 °F) at 760 mmHg (hydrochloride)
  • O=C(c1ccccc1)C(NCC)C
  • InChI=1S/C11H15NO/c1-3-12-9(2)11(13)10-7-5-4-6-8-10/h4-9,12H,3H2,1-2H3 Yes check.svgY
  • Key:LYMHIBZGTAPASQ-UHFFFAOYSA-N Yes check.svgY
   (verify)

Ethcathinone, also known as ethylpropion or ETH-CAT, is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is an active metabolite of the prodrug diethylcathinone and is fully responsible for its effects. Ethcathinone has been identified as an ingredient in both quasi-legal "party pills", [3] and, along with mephedrone, has also been reported as having been sold as "ecstasy" in the Australian city of Cairns. [4] [5]

Contents

Pharmacology

The pharmacology for ethcathinone appeared alongside other psychostimulants in a paper by Rothman and Baumann in 2006. [6] The predominant two modes of action for ethcathinone is as a moderately active releaser of noradrenaline (EC50 = 99.3 nM); [6] however it is only a relatively weak inhibitor of dopamine reuptake (Ki = 1,014 nM). [6]

Since diethylcathinone appears to be an inactive prodrug and only becomes active after it has been further metabolized to ethcathinone, [6] it thereby would appear rational to consider that ethcathinone would also be expected to be N-dealkylated upon its consumption to the more active drug cathinone that is more able to reliably stimulate the release of dopamine. However, in contrast to diethylcathinone, ethcathinone is not universally considered to be a prodrug since (as is the case with tramadol, codeine, and MDMA) it is already active in its own right, therefore being excluded from the category by some of the more strict definitions.

Ethcathinone, along with mephedrone and flephedrone, was banned in Denmark on December 18, 2008.

As of October 2015 Ethcathinone is a controlled substance in China. [7]

This compound is banned in the United States, being a positional isomer of mephedrone. [8]

See also

Related Research Articles

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<span class="mw-page-title-main">Butylone</span> Entactogen, psychedelic, and stimulant drug of the phenethylamine class

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<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

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

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<span class="mw-page-title-main">Mephedrone</span> Synthetic stimulant drug

Mephedrone, also known as 4-methylmethcathinone, 4-MMC, and 4-methylephedrone, is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include drone, M-CAT, White Magic, meow meow and bubble. It is chemically similar to the cathinone compounds found in the khat plant of eastern Africa. It comes in the form of tablets or crystals, which users can swallow, snort or inject, producing effects similar to those of MDMA, amphetamines and cocaine.

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinopropiophenone</span> Chemical compound

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<span class="mw-page-title-main">Flephedrone</span> Stimulant designer drug

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<span class="mw-page-title-main">Methiopropamine</span> Structural analog of methamphetamine

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<span class="mw-page-title-main">4-Methylethcathinone</span> Stimulant designer drug

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<span class="mw-page-title-main">3,4-Dimethylmethcathinone</span> Designer stimulant drug

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<span class="mw-page-title-main">Pentedrone</span> Stimulant designer drug of the cathinone class

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<span class="mw-page-title-main">3-Methylmethcathinone</span> Substituted cathinone designer drug

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<i>alpha</i>-Pyrrolidinohexiophenone Chemical compound

α-Pyrrolidinohexiophenone is a synthetic stimulant drug of the cathinone class developed in the 1960s which has been reported as a novel designer drug.

<span class="mw-page-title-main">4-Chloromethcathinone</span> Simulant drug of the cathinone class

4-Chloromethcathinone is a stimulant drug of the cathinone class that has been sold online as a designer drug.

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ DEA Controlled Substances Act listing dated 21-Jul-15
  3. ↑ Camilleri A, Johnston MR, Brennan M, Davis S, Caldicott DG (April 2010). "Chemical analysis of four capsules containing the controlled substance analogues 4-methylmethcathinone, 2-fluoromethamphetamine, alpha-phthalimidopropiophenone and N-ethylcathinone". Forensic Science International. 197 (1–3): 59–66. doi:10.1016/j.forsciint.2009.12.048. PMID   20074881.
  4. ↑ Killer pills hit Cairns [ dead link ]
  5. ↑ Police warn of potentially fatal 'fake ecstasy'
  6. 1 2 3 4 Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry. 6 (17): 1845–59. doi:10.2174/156802606778249766. PMID   17017961.
  7. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  8. ↑ DEA Controlled Substances Act listing dated 21-Jul-15
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