N-Ethylhexedrone

N-Ethylhexedrone
Legal status
Legal status
Pharmacokinetic data
MetabolismNeurometabolic
Identifiers
  • 2-(Ethylamino)-1-phenylhexan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC14H21NO
Molar mass219.328 g·mol−1
3D model (JSmol)
  • CCCCC(NCC)C(=O)c1ccccc1
  • InChI=1S/C14H21NO/c1-3-5-11-13(15-4-2)14(16)12-9-7-6-8-10-12/h6-10,13,15H,3-5,11H2,1-2H3
  • Key:CWNKMHIETKEBCA-UHFFFAOYSA-N

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class[2][3] that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively.[4] N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s[5] which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV).[6][failed verification] Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug.[7][8][9] In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.[10]

N-Ethylhexedrone was first synthesized by Boehringer Ingelheim in 1964.[11] It appears to have emerged on the online research chemical market in late 2015.[12] It is an example of a novel psychoactive substance specifically chosen to mimic the features of prohibited substances and bypass drug laws. It is one of a number of substances collectively referred to as "bath salts".[13]

User reports characterize N-ethylhexedrone as having euphoric stimulant effects comparable to those of crack-cocaine and α-PVP-type compounds, particularly when they are insufflated or vaporized. Like other substituted cathinones, N-ethylhexedrone has gained notoriety for its association with compulsive redosing and addictive behaviors when abused.

  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. ^ Matsuta S, Katagi M, Nishioka H, Kamata H, Sasaki K, Shima N, et al. (2014). "Structural characterization of cathinone-type designer drugs by EI mass spectrometry". Japanese Journal of Forensic Science and Technology (in Japanese). 19 (2): 77–89. doi:10.3408/jafst.19.77.
  3. ^ Kuś P, Rojkiewicz M, Kusz J, Książek M, Sochanik A (July 2019). "Spectroscopic characterization and crystal structures of four hydrochloride cathinones: N-ethyl-2-amino-1-phenylhexan-1-one (hexen, NEH), N-methyl-2-amino-1-(4-methylphenyl)-3-methoxypropan-1-one (mexedrone), N-ethyl-2-amino-1-(3,4-methylenedioxyphenyl)pentan-1-one (ephylone) and N-butyl-2-amino-1-(4-chlorophenyl)propan-1-one (4-chlorobutylcathinone)". Forensic Toxicology. 37 (2): 456–464. doi:10.1007/s11419-019-00477-y. hdl:20.500.12128/9638.
  4. ^ Eshleman AJ, Nagarajan S, Wolfrum KM, Reed JF, Swanson TL, Nilsen A, Janowsky A (March 2019). "Structure-activity relationships of bath salt components: substituted cathinones and benzofurans at biogenic amine transporters". Psychopharmacology. 236 (3): 939–952. doi:10.1007/s00213-018-5059-5. PMC 6500773. PMID 30397775.
  5. ^ DE 1545591, Herbert K, Karl Z, Gerhard L, "Verfahren zur Herstellung von α-Aminoketonen mit heterocyclischer Aminogruppe", published 28 May 1965, assigned to Boehringer Ingelheim 
  6. ^ Kolanos R, Solis E, Sakloth F, De Felice LJ, Glennon RA (December 2013). ""Deconstruction" of the abused synthetic cathinone methylenedioxypyrovalerone (MDPV) and an examination of effects at the human dopamine transporter". ACS Chemical Neuroscience. 4 (12): 1524–1529. doi:10.1021/cn4001236. PMC 3867964. PMID 24116392.
  7. ^ "2-(Ethylamino)-1-phenylhexan-1-one". New Synthetic Drugs Database. Archived from the original on 2017-05-20. Retrieved 2016-08-28.
  8. ^ "Analytical Report - N-Ethylhexedrone" (PDF). European Project RESPONSE.
  9. ^ Liu C, Jia W, Li T, Hua Z, Qian Z (August 2017). "Identification and analytical characterization of nine synthetic cathinone derivatives N-ethylhexedrone, 4-Cl-pentedrone, 4-Cl-α-EAPP, propylone, N-ethylnorpentylone, 6-MeO-bk-MDMA, α-PiHP, 4-Cl-α-PHP, and 4-F-α-PHP". Drug Testing and Analysis. 9 (8): 1162–1171. doi:10.1002/dta.2136. PMID 27863142.
  10. ^ "Emerging Threat Report: Annual 2018" (PDF). Special Testing and Research Laboratory, Drug Enforcement Administration.
  11. ^ Critical Review Report: N-Ethylhexedrone (PDF). Expert Committee on Drug Dependence (ECDD). Vol. Forty-second Meeting. World Health Organisation (WHO). October 2019.
  12. ^ "N-Ethylhexedrone". Google Trends. Retrieved October 16, 2020.
  13. ^ Eshleman AJ, Nagarajan S, Wolfrum KM, Reed JF, Swanson TL, Nilsen A, Janowsky A (March 2019). "Structure-activity relationships of bath salt components: substituted cathinones and benzofurans at biogenic amine transporters". Psychopharmacology. 236 (3): 939–952. doi:10.1007/s00213-018-5059-5. eISSN 1432-2072. OCLC 2409222. PMC 6500773. PMID 30397775.