Substituted phenethylamine

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

Detection

methodRequirement
UV spectrometryReagent needed

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

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<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">Cathinone</span> Chemical compound

Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis, also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs.

<span class="mw-page-title-main">2C (psychedelics)</span> Class of chemical compounds

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.

β-Methylphenethylamine Chemical compound

β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.

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

Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances.

These drugs are known in the UK as controlled drugs, 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.

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, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

DO<em>x</em> 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">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.

<span class="mw-page-title-main">6-(2-Aminopropyl)indole</span> Chemical compound

6-(2-Aminopropyl)indole is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czech Republic in July 2016.

βk-2C-B Chemical compound

βk-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 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">Structural scheduling of synthetic cannabinoids</span>

To combat the illicit synthetic cannabinoid industry many jurisdictions have created a system to control these cannabinoids through their general structure as opposed to their specific identity. In this way new analogs are already controlled before they are even created. A large number of cannabinoids have been grouped into classes based on similarities in their chemical structure, and these classes have been widely adopted across a variety of jurisdictions.

<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 overdose potential and sellers passing off the compounds in the series as LSD.

References

  1. ↑ 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.
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