Substituted phenethylamine

Last updated

Substituted phenethylamine
Drug class
Phenylethyl Amine General Formula V1.svg
The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when
R2=R3=R4=R5=R6=RN=Rα=Rβ=H.
Class identifiers
Chemical class Substituted derivatives of phenethylamine
Legal status
In Wikidata
The structural formula of phenethylamine Phenethylamine2DCSD.svg
The structural formula of phenethylamine

Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; [note 1] the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

Contents

The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino (NH) group via a two-carbon sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with a specific group of atoms.

Many substituted phenethylamines are psychoactive drugs which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., 3,4,5-trimethoxyphenethylamine a.k.a. mescaline), 2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), entactogen (e.g. MDA), appetite suppressants (e.g. phentermine), nasal decongestants and bronchodilators (e.g., levomethamphetamine and pseudoephedrine), antidepressants (e.g. bupropion and phenelzine), antiparkinson agents (e.g., selegiline), and vasopressors (e.g., ephedrine), among others. [1] [2] Many of these psychoactive compounds exert their pharmacological effects primarily by modulating monoamine neurotransmitter systems; however, there is no mechanism of action or biological target that is common to all members of this subclass.[ medical citation needed ]

Numerous endogenous compounds – including hormones, catecholamines such as dopamine and noradrenaline, and many trace amines (e.g. adrenaline, phenethylamine itself, tyramine, thyronamine, and iodothyronamine) – are substituted phenethylamines. Several notable recreational drugs, such as MDMA (ecstasy), methamphetamine, and cathinone, are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.

List of substituted phenethylamines

Selected Phenethylamines
Chemical

Structure

Short NameRNRαRβR2R3R4R5Full NameBiologic activity
Meta-Tyramine.svg meta-Tyramine OH 3-hydroxyphenethylamine Trace amine
Tyramine.svg para-Tyramine OH4-hydroxyphenethylamine Trace amine
Dopamine.svg Dopamine OHOH3,4-dihydroxyphenethylamineCatecholamine neurotransmitter
Epinephrine.svg Epinephrine (Adrenaline) CH3 OHOHOHβ,3,4-trihydroxy-N-methyl phenethylamineCatecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine.svg Norepinephrine (Noradrenaline)OHOHOHβ,3,4-trihydroxyphenethylamineCatecholamine neurotransmitter/Fight or Flight hormone
Norfenefrine.png Norfenefrine OHOHβ,3-dihydroxyphenethylamine Trace amine
Octapamine.svg para-Octopamine OHOHβ,4-dihydroxyphenethylamine Trace aminergic α-adrenoceptor agonist
6-Hydroxydopamine.svg Oxidopamine OHOHOH2,4,5-trihydroxyphenethylamineneurotoxic agent for the dopamine and norepinephrine receptors
Phenylephrine.png Phenylephrine CH3OHOHβ,3-dihydroxy-N-methylphenethylamineα-adrenergic agonist; decongestant
Isoprenaline.svg Isoprenaline CH(CH3)2OHOHOHβ,3-dihydroxy-N-isopropylphenethylamineβ-adrenergic agonist; decongestant
Salbutamol.svg Salbutamol C(CH3)3OHCH2OHOHβ,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamineShort-action β2-adrenergic agonist
Beta-methylphenethylamine.png β-Methylphenethylamine CH3β-methylphenethylamine Stimulant
Amphetamine.svg Amphetamine CH3α-methylphenethylamine Monoamine releasing agent; Stimulant
Methylphenethylamine.png N-Methylphenethylamine CH3N-methylphenethylamine Trace amine; endogenous amphetamine isomer
N,N-Dimethylphenethylamine.svg N,N-Dimethylphenethylamine (CH3)2N,N-dimethylphenethylamineTrivial effects (used as a food additive and flavoring agent)
Methamphetamine.svg Methamphetamine CH3CH3N-methylamphetamine; N,α-dimethylphenethylamine Monoamine releasing agent; stimulant; neurotoxin
Fentermina.svg Phentermine (CH3)2α-methylamphetamine; α,α-dimethylphenethylamine Stimulant, anorectic
2-methylamphetamine.svg Ortetamine CH3CH32-methylamphetamine; 2,α-dimethylphenethylamine Stimulant, anorectic
Phenelzine.svg Phenelzine NH2β-phenylethylhydrazine Monoamine oxidase inhibitor
Tranylcypromine Structure.svg Tranylcypromine -CH2-2-phenylcyclopropylamine Monoamine oxidase inhibitor
Selegiline.svg Selegiline -CH2-C≡CHCH3N,α-dimethyl-N-2-propynylphenethylamine MAO-B selective monoamine oxidase inhibitor
Methylphenidate-2D-skeletal.svg Methylphenidate -CH2-CH2-CH2-CH2-C(OCH3)=ON,α-butylene-β-methoxycarbonylphenethylamine NDRI; Stimulant
Ephedrine-ifa.png Ephedrine / Pseudoephedrine CH3CH3OHN-methyl-β-hydroxyamphetamine Releasing agent; stimulant; decongestant
Pseudonorephedrine.png Cathine CH3OHd-β-hydroxyamphetamineModerately selective norepinephrine releasing agent
Cathinone.svg Cathinone CH3=Oβ-ketoamphetamineSelective norepinephrine and dopamine releasing agent
Methcathinone skeletal.svg Methcathinone CH3CH3=ON-methylcathinoneSelective norepinephrine and dopamine releasing agent
Mephedrone-2D-skeletal.svg Mephedrone CH3CH3=OCH34-methylmethcathinoneStimulant, unknown pharmacodynamic actions
Ethcathinone.svg Ethcathinone CH2CH3CH3=ON-ethylcathinoneStimulant and norepinephrine releasing agent
Amfepramone.svg Amfepramone (diethylpropion)C2H5, C2H5 [note 2] CH3=ON-diethyl-β-ketoamphetamineAnorectic
Bupropion 1.svg Bupropion C(CH3)3CH3=OCl5-chloro-N-tert-butyl-β-ketoamphetamine NDRI
3-trifluoromethylamphetamine.svg Norfenfluramine CH3 CF3 3-trifluoromethyl-amphetamine SSRA
Fenfluramine2DCSD.svg Fenfluramine CH2CH3CH3CF33-trifluoromethyl-N-ethylamphetamine SSRA
5APB.svg 5-APB CH3-CH=CH-O-5-(2-aminopropyl)benzofuran Stimulant, entactogen
6APB.svg 6-APB CH3-O-CH=CH-6-(2-aminopropyl)benzofuran Stimulant, entactogen
MDA-2D-skeletal.svg MDA CH3-O-CH2-O-3,4-methylenedioxy-amphetamine Stimulant, psychedelic, entactogen
MDEA.svg MDEA CH2CH3CH3-O-CH2-O-3,4-methylenedioxy-N-ethylamphetamine Psychedelic, entactogen, and releasing agent
MDMA (simple).svg MDMA CH3CH3-O-CH2-O-3,4-methylenedioxy-N-methylamphetamine Psychedelic, entactogen, and releasing agent
MDMC.svg MDMC CH3CH3=O-O-CH2-O-3,4-methylenedioxymethcathinone Psychedelic, entactogen, and releasing agent
MMDA-structure.png MMDA CH3-O-CH2-O-OCH35-methoxy-3,4-methylenedioxy-amphetamine Stimulant, psychedelic and entactogen
MMDMA-structure.png MMDMA CH3CH3-O-CH2-O-OCH35-methoxy-3,4-methylenedioxy-N-methylamphetamine Psychedelic, entactogen, and releasing agent
Lophophine.png Lophophine -O-CH2-O-OCH35-methoxy-3,4-methylenedioxyphenethylamine Psychedelic and entactogen
Mescaline Structural Formulae bondline.svg Mescaline OCH3 OCH3OCH33,4,5-trimethoxy phenethylamine Psychedelic and entactogen
Proscaline.svg Proscaline OCH3OCH2CH2CH3OCH32-(3,5-dimethoxy-4-propoxyphenyl)ethanamine Psychedelic and entactogen
Metaescaline.svg Metaescaline OCH2CH3 OCH3OCH32-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine Psychedelic and entactogen
Allylescaline.svg Allylescaline OCH3OCH2CH1CH2OCH34-Allyloxy-3,5-dimethyloxyphenylethylamine Psychedelic and entactogen
Methallylescaline.svg Methallylescaline OCH3OCH2C(CH2CH3)OCH34-Methallyloxy-3,5-dimethoxyphenethylamine Psychedelic and entactogen
Asymbescaline.png Asymbescaline OCH2CH3OCH2CH3OCH33,4-Diethoxy-5-methoxyphenethylamine Psychedelic and euphoriant
2,5-dimethoxy-4-methylamphetamine.svg DOM CH3OCH3CH3OCH32,5-dimethoxy-4-methylamphetamine Psychedelic
2,5-dimethoxy-4-bromoamphetamine.svg DOB CH3OCH3 Br OCH32,5-dimethoxy-4-bromo amphetamine Psychedelic
2,5-dimethoxy-4-chloroamphetamine.svg DOC CH3OCH3 Cl OCH32,5-dimethoxy-4-chloro amphetamine Psychedelic
2,5-dimethoxy-4-iodoamphetamine.svg DOI CH3OCH3 I OCH32,5-dimethoxy-4-iodo amphetamine Psychedelic
2,5-dimethoxy-4-nitroamphetamine.svg DON CH3OCH3 NO2 OCH32,5-dimethoxy-4-nitro amphetamine Stimulant
2C-B-Chemdraw.png 2C-B OCH3BrOCH32,5-dimethoxy-4-bromophenethylamine Psychedelic, stimulant, entactogen and euphoriant
Bk-2C-B.svg βk-2C-B =OOCH3BrOCH32,5-dimethoxy-4-bromo-β-ketophenethylamine Psychedelic, stimulant, entactogen and euphoriant
2C-C-Chemdraw.png 2C-C OCH3ClOCH32,5-dimethoxy-4-chlorophenethylamine Psychedelic
2C-F-Chemdraw.png 2C-F OCH3 F OCH32,5-dimethoxy-4-fluoro phenethylamine Psychedelic
2C-I-Chemdraw.png 2C-I OCH3IOCH32,5-dimethoxy-4-iodophenethylamine Psychedelic, stimulant
2C-D-Chemdraw.png 2C-D OCH3CH3OCH32,5-dimethoxy-4-methylphenethylamine Psychedelic, stimulant
2C-E-Chemdraw.png 2C-E OCH3CH2-CH3OCH32,5-dimethoxy-4-ethylphenethylamine Psychedelic
2C-P-Chemdraw.png 2C-P OCH3CH2-CH3-CH3OCH32,5-dimethoxy-4-propylphenethylamine Entactogen, euphoriant and Psychedelic
2C-N 2DACS.svg 2C-N OCH3NO2OCH32,5-dimethoxy-4-nitrophenethylamine euphoriant
2C-T-2-Chemdraw.png 2C-T-2 OCH3 S-CH2CH3OCH32,5-dimethoxy-4-ethylthio-phenethylamine Psychedelic
2C-T-4-Chemdraw.png 2C-T-4 OCH3S-CH(CH3)2 OCH32,5-dimethoxy-4-isopropyl thio-phenethylamine Psychedelic
2C-T-7-Chemdraw.png 2C-T-7 OCH3S-CH2CH2CH3OCH32,5-dimethoxy-4-propylthio-phenethylamine Psychedelic
2C-T-8-Chemdraw.png 2C-T-8 OCH3S-CH2-C3H5 OCH32,5-dimethoxy-4-cyclopropyl methylthio-phenethylamine Psychedelic
2C-T-19.png 2C-T-19 OCH3S-C(CH3)3OCH32,5-dimethoxy-4-tert-butylthio-phenethylamine Psychedelic
2C-T-21-Chemdraw.png 2C-T-21 OCH3S-CH2-CH2-FOCH32,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine Psychedelic and euphoriant
2C-B-NBOMe-skeletal.svg 25B-NBOMe [3] CH2-C6H4-OCH3OCH3BrOCH32-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-C-NBOMe-skeletal.svg 25C-NBOMe CH2-C6H4-OCH3OCH3ClOCH32-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25F-NBOMe structure.png 25F-NBOMeCH2-C6H4-OCH3OCH3FOCH32-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-I-NBOMe-skeletal.svg 25I-NBOMe CH2-C6H4-OCH3OCH3IOCH32-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25D-NBOMe2DACS.svg 25D-NBOMe CH2-C6H4-OCH3OCH3CH2OCH32-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
2C-E-NBOMe 2DACS.svg 25E-NBOMe CH2-C6H4-OCH3OCH3CH2-CH3OCH32-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
25P-NBOMe.svg 25P-NBOMe CH2-C6H4-OCH3OCH3CH2-CH3-CH3OCH32-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine Psychedelic
Mescaline-NBOMe.svg Mescaline-NBOMe CH2-C6H4-OCH3 OCH3 OCH3OCH3N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine Psychedelic
25B-NBOH structure.png 25B-NBOH CH2–C6H4–OHOCH3BrOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine Psychedelic
NBOH-2CC structure.png 25C-NBOH CH2–C6H4–OHOCH3ClOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine Psychedelic
2C-I-NBOH-skeletal.svg 25I-NBOH CH2–C6H4–OHOCH3IOCH3N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
25i-NBF.svg 25I-NBF CH2–C6H4–FOCH3IOCH3N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine Psychedelic
Short NameRNRαRβR2R3R4R5Full NameBiologic activity

Detection

methodRequirement
UV spectrometryReagent needed

Detection of substituted phenethylamines, which include compounds such as 2C-B, MDMA, and other designer drugs, involves various analytical methods aimed at identifying these psychoactive substances. These compounds are structurally similar to amphetamines, making their detection challenging due to potential cross-reactivity in standard drug tests. Techniques like gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), and immunoassay screenings are commonly employed for accurate identification. Advanced methods like high-performance liquid chromatography (HPLC) allow for precise separation and quantification of these substances even at low concentrations. Given the rising use of these drugs in recreational settings, developing sensitive and specific detection techniques remains crucial in forensic toxicology and clinical diagnostics.

See also

Notes

  1. In other words, all of the compounds that belong to this class are structural analogs of phenethylamine.
  2. Two ethyl groups attached to the amine group

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

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

Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

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

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

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

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">2C (psychedelics)</span> Family of phenethylamine psychedelics

2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL. Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

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

4'-Methyl-α-pyrrolidinopropiophenone is a stimulant drug and substituted cathinone. It is structurally very similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. 4-MePPP was sold in Germany as a designer drug in the late 1990s and early 2000s, along with a number of other pyrrolidinophenone derivatives. Although it has never achieved the same international popularity as its better-known relations α-PPP and MDPV, 4-MePPP is still sometimes found as an ingredient of grey-market "bath salt" blends such as "NRG-3".

<span class="mw-page-title-main">4'-Methoxy-α-pyrrolidinopropiophenone</span> Stimulant recreational drug

4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP) is a stimulant designer drug of the pyrrolidinophenone class. It has the potential to produce euphoria, an effect shared with other classical stimulants.

These drugs are known in the UK as controlled drug, because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other drugs which are controlled by the Medicines Act but not by the Misuse of Drugs Act, and some other drugs are controlled by other laws.

<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

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

Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.

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

3-Fluoromethcathinone is a chemical compound of the phenethylamine, amphetamine, and cathinone classes that has been sold online as a designer drug. It is a structural isomer of flephedrone (4-fluoromethcathinone).

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

βk-2C-B Chemical compound

βk-2C-B (βeta-keto-4-bromo-2,5-dimethoxyphenylamine), also known as bk-2C-B, is a novel psychedelic substance. It is the beta (β) ketone structural analogue of 2C-B, a psychedelic drug of the 2C family. It is used as a recreational drug, usually taken orally. βk-2C-B is a controlled substance in Canada, Germany, Switzerland, and the United Kingdom.

<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 Stimulant of the cathinone class

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">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.

References

  1. Inan, Funda; Brunt, Tibor M.; Contrucci, Ramon R.; Hondebrink, Laura; Franssen, Eric J. F. (2020). "Novel Phenethylamines and Their Potential Interactions With Prescription Drugs: A Systematic Critical Review". Therapeutic Drug Monitoring. 42 (2): 271–281. doi:10.1097/ftd.0000000000000725. ISSN   0163-4356. PMID   32022784. S2CID   211035606.
  2. Wills, Brandon; Erickson, Timothy (2 February 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". Medical Toxicology of Drug Abuse: 156–192. doi:10.1002/9781118105955.ch10. ISBN   978-0-471-72760-6.
  3. Custodio, Raly James Perez; Sayson, Leandro Val; Botanas, Chrislean Jun; Abiero, Arvie; You, Kyung Yi; Kim, Mikyung; Lee, Hyun Jun; Yoo, Sung Yeun; Lee, Kun Won; Lee, Yong Sup; Seo, Joung-Wook (2019). "25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential". Addiction Biology. 25 (6): e12850. doi:10.1111/adb.12850. ISSN   1369-1600. PMID   31749223. S2CID   208217863.