4-Ethylamphetamine

Last updated
4-Ethylamphetamine
4-Ethylamphetamine.svg
Legal status
Legal status
Identifiers
  • 1-(4-ethylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C11H17N
Molar mass 163.264 g·mol−1
3D model (JSmol)
  • CCC1=CC=C(C=C1)CC(C)N
  • InChI=1S/C11H17N/c1-3-10-4-6-11(7-5-10)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3
  • Key:VHFLVGIMDGXALR-UHFFFAOYSA-N

4-Ethylamphetamine (4-EA) is a substituted amphetamine derivative which has been sold as a designer drug. It is mainly known as a synthetic intermediate used as a building block to manufacture larger molecules, [1] [2] but 4-EA is closely related in chemical structure to designer drugs such as 4-methylamphetamine and 4-ethylmethcathinone, and is both a synthetic precursor and a metabolite of the 25-NB derivative 4-EA-NBOMe. [3]

See also

Related Research Articles

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<span class="mw-page-title-main">25I-NBOMe</span> Synthetic hallucinogen

25I-NBOMe is a novel synthetic psychoactive substance with strong hallucinogenic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. The recreational usage of 25I is associated with severe intoxication and deaths in humans.

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinobutiophenone</span> Group of stereoisomers

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<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Anecdotal reports from users suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 µg, making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

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<span class="mw-page-title-main">25C-NBOMe</span> Psychedelic drug

25C-NBOMe is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011. It acts as a potent agonist of the 5HT2A receptor, and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET). Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

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

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<span class="mw-page-title-main">6-MAPB</span> Chemical compound

6-MAPB is a psychedelic and entactogenic drug which is structurally related to 6-APB and MDMA. It is not known to have been widely sold as a "designer drug" but has been detected in analytical samples taken from individuals hospitalised after using drug combinations that included other benzofuran derivatives. 6-MAPB was banned in the UK in June 2013, along with 9 other related compounds which were thought to produce similar effects.

<span class="mw-page-title-main">25D-NBOMe</span> Chemical compound

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<span class="mw-page-title-main">25N-NBOMe</span> Chemical compound

25N-NBOMe is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT2A receptor. 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.

<span class="mw-page-title-main">25E-NBOMe</span> Chemical compound

25E-NBOMe is a derivative of the phenethylamine 2C-E. It acts in a similar manner to related compounds such as 25I-NBOMe, which are potent agonists at the 5HT2A receptor. 25E-NBOMe has been sold as a drug and produces similar effects in humans to related compounds such as 25I-NBOMe and 25C-NBOMe.

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

Ephenidine is a dissociative anesthetic that has been sold online as a designer drug. It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned.

<span class="mw-page-title-main">Substituted benzofuran</span> Class of chemical compounds

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.

<i>N</i>-Ethylhexedrone Chemical compound

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

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

NPDPA is a dissociative anesthetic that has been sold online as a designer drug. It was first identified in Germany in 2008, and while it has never been as widely sold as related compounds such as diphenidine and ephenidine, it has continued to show up in seized drug samples occasionally, and was banned in Sweden in 2015.

<span class="mw-page-title-main">25-NB</span> Family of serotonergic psychedelics

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.

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

4-EA-NBOMe is a substituted amphetamine and 25-NB derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Germany in 2014, but while its analytical properties and metabolism have been studied, its pharmacology remains unknown.

<span class="mw-page-title-main">25E-NBOH</span> Chemical compound

25E-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-E. It was first developed by Martin Hansen at the University of Copenhagen in 2010 as a brain imaging agent, but has subsequently been sold as a designer drug, first being identified in Brazil in 2018 on seized blotter paper, as well as in Slovenia. It acts as a potent serotonin receptor agonist with similar affinity to better-known compounds such as 25I-NBOMe at 5-HT2A and 5-HT2C receptors.

<span class="mw-page-title-main">2C-E-FLY</span> Chemical compound

2C-E-FLY is a recreational designer drug with psychedelic effects. It is slightly less potent than 2C-E or 2C-B-FLY in animal studies but retains drug-appropriate responding.

<span class="mw-page-title-main">25T7-NBOMe</span> Chemical compound

25T7-NBOMe, is a substituted phenethylamine derivative from the 25-NB family. It acts as an agonist at the 5-HT2A and 5-HT2C serotonin receptors, has psychedelic effects and has been sold as a designer drug.

References

  1. Arnold MJ, Duriatti AD, Jung M, Katz RB, Liebeschuetz JW (1995). "Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors". Pesticide Science. 44 (4): 341–355. doi:10.1002/ps.2780440406.
  2. Caspar AT, Meyer MR, Westphal F, Weber AA, Maurer HH (October 2018). "Nano liquid chromatography-high-resolution mass spectrometry for the identification of metabolites of the two new psychoactive substances N-(ortho-methoxybenzyl)-3,4-dimethoxyamphetamine and N-(ortho-methoxybenzyl)-4-methylmethamphetamine". Talanta. 188: 111–123. doi:10.1016/j.talanta.2018.05.064. PMID   30029353. S2CID   51705002.
  3. Caspar AT, Westphal F, Meyer MR, Maurer HH (January 2018). "LC-high resolution-MS/MS for identification of 69 metabolites of the new psychoactive substance 1-(4-ethylphenyl-)-N-[(2-methoxyphenyl)methyl] propane-2-amine (4-EA-NBOMe) in rat urine and human liver S9 incubates and comparison of its screening power with further MS techniques". Analytical and Bioanalytical Chemistry. 410 (3): 897–912. doi:10.1007/s00216-017-0526-0. PMID   28762065. S2CID   206923339.