Substituted phenethylamine

Substituted phenethylamine
Substituted phenethylamine
Drug class
	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

Last updated March 13, 2024

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.

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
Short Name	R^N	R^α	R^β	R²	R³	R⁴	R⁵	Full Name	Biologic activity
meta-Tyramine					OH			3-hydroxyphenethylamine	Trace amine
para-Tyramine						OH		4-hydroxyphenethylamine	Trace amine
Dopamine					OH	OH		3,4-dihydroxyphenethylamine	Catecholamine neurotransmitter
Epinephrine (Adrenaline)	CH₃		OH		OH	OH		β,3,4-trihydroxy-N-methyl phenethylamine	Catecholamine neurotransmitter/Fight or Flight hormone
Norepinephrine (Noradrenaline)			OH		OH	OH		β,3,4-trihydroxyphenethylamine	Catecholamine neurotransmitter/Fight or Flight hormone
Norfenefrine			OH		OH			β,3-dihydroxyphenethylamine	Trace amine
para-Octopamine			OH			OH		β,4-dihydroxyphenethylamine	Trace aminergic α-adrenoceptor agonist
Oxidopamine				OH		OH	OH	2,4,5-trihydroxyphenethylamine	neurotoxic agent for the dopamine and norepinephrine receptors
Phenylephrine	CH₃		OH		OH			β,3-dihydroxy-N-methylphenethylamine	α-adrenergic agonist; decongestant
Isoprenaline	CH(CH₃)₂		OH		OH	OH		β,3-dihydroxy-N-methylphenethylamine	β-adrenergic agonist; decongestant
Salbutamol	C(CH₃)₃		OH		CH₂OH	OH		β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine	Short-action β₂-adrenergic agonist
β-Methylphenethylamine			CH₃					β-methylphenethylamine	Stimulant
Amphetamine		CH₃						α-methylphenethylamine	Monoamine releasing agent; Stimulant
N-Methylphenethylamine	CH₃							N-methylphenethylamine	Trace amine; endogenous amphetamine isomer
N,N-Dimethylphenethylamine	(CH₃)₂							N,N-dimethylphenethylamine	Trivial effects (used as a food additive and flavoring agent)
Methamphetamine	CH₃	CH₃						N-methylamphetamine; N,α-dimethylphenethylamine	Monoamine releasing agent; stimulant; neurotoxin
Phentermine		(CH₃)₂						α-methylamphetamine; α,α-dimethylphenethylamine	Stimulant, anorectic
Ortetamine		CH₃		CH₃				2-methylamphetamine; 2,α-dimethylphenethylamine	Stimulant, anorectic
Phenelzine	NH₂							β-phenylethylhydrazine	Monoamine oxidase inhibitor
Tranylcypromine		-CH₂-						2-phenylcyclopropylamine	Monoamine oxidase inhibitor
Selegiline	-CH₂-C≡CH	CH₃						N,α-dimethyl-N-2-propynylphenethylamine	MAO-B selective monoamine oxidase inhibitor
Methylphenidate	-CH₂-CH₂-CH₂-CH₂-		C(OCH₃)=O					N,α-butylene-β-methoxycarbonylphenethylamine	NDRI; Stimulant
Ephedrine / Pseudoephedrine	CH₃	CH₃	OH					N-methyl-β-hydroxyamphetamine	Releasing agent; stimulant; decongestant
Cathine		CH₃	OH					d-β-hydroxyamphetamine	Moderately selective norepinephrine releasing agent
Cathinone		CH₃	=O					β-ketoamphetamine	Selective norepinephrine and dopamine releasing agent
Methcathinone	CH₃	CH₃	=O					N-methylcathinone	Selective norepinephrine and dopamine releasing agent
Mephedrone	CH₃	CH₃	=O			CH₃		4-methylmethcathinone	Stimulant, unknown pharmacodynamic actions
Ethcathinone	CH₂CH₃	CH₃	=O					N-ethylcathinone	Stimulant and norepinephrine releasing agent
Amfepramone (diethylpropion)	C₂H₅, C₂H₅^{[note 2]}	CH₃	=O					N-diethyl-β-ketoamphetamine	Anorectic
Bupropion	C(CH₃)₃	CH₃	=O				Cl	5-chloro-N-tert-butyl-β-ketoamphetamine	NDRI
Norfenfluramine		CH₃			CF₃			3-trifluoromethyl-amphetamine	SSRA
Fenfluramine	CH₂CH₃	CH₃			CF₃			3-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	CH₂CH₃	CH₃			-O-CH₂-O-			3,4-methylenedioxy-N-ethylamphetamine	Psychedelic, entactogen, and releasing agent
MDMA	CH₃	CH₃			-O-CH₂-O-			3,4-methylenedioxy-N-methylamphetamine	Psychedelic, entactogen, and releasing agent
MDMC	CH₃	CH₃	=O		-O-CH₂-O-			3,4-methylenedioxymethcathinone	Psychedelic, entactogen, and releasing agent
MMDA		CH₃			-O-CH₂-O-		OCH₃	5-methoxy-3,4-methylenedioxy-amphetamine	Stimulant, psychedelic and entactogen
MMDMA	CH₃	CH₃			-O-CH₂-O-		OCH₃	5-methoxy-3,4-methylenedioxy-N-methylamphetamine	Psychedelic, entactogen, and releasing agent
Lophophine					-O-CH₂-O-		OCH₃	5-methoxy-3,4-methylenedioxyphenethylamine	Psychedelic and entactogen
Mescaline					OCH₃	OCH₃	OCH₃	3,4,5-trimethoxy phenethylamine	Psychedelic and entactogen
Proscaline					OCH₃	OCH₂CH₂CH₃	OCH₃	2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine	Psychedelic and entactogen
Metaescaline					OCH₂CH₃	OCH₃	OCH₃	2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine	Psychedelic and entactogen
Allylescaline					OCH₃	OCH₂CH₁CH₂	OCH₃	4-Allyloxy-3,5-dimethyloxyphenylethylamine	Psychedelic and entactogen
Methallylescaline					OCH₃	OCH₂C(CH₂CH₃)	OCH₃	4-Methallyloxy-3,5-dimethoxyphenethylamine	Psychedelic and entactogen
Asymbescaline					OCH₂CH₃	OCH₂CH₃	OCH₃	3,4-Diethoxy-5-methoxyphenethylamine	Psychedelic and euphoriant
DOM		CH₃		OCH₃		CH₃	OCH₃	2,5-dimethoxy-4-methylamphetamine	Psychedelic
DOB		CH₃		OCH₃		Br	OCH₃	2,5-dimethoxy-4-bromo amphetamine	Psychedelic
DOC		CH₃		OCH₃		Cl	OCH₃	2,5-dimethoxy-4-chloro amphetamine	Psychedelic
DOI		CH₃		OCH₃		I	OCH₃	2,5-dimethoxy-4-iodo amphetamine	Psychedelic
DON		CH₃		OCH₃		NO₂	OCH₃	2,5-dimethoxy-4-nitro amphetamine	Stimulant
2C-B				OCH₃		Br	OCH₃	2,5-dimethoxy-4-bromophenethylamine	Psychedelic, stimulant, entactogen and euphoriant
βk-2C-B			=O	OCH₃		Br	OCH₃	2,5-dimethoxy-4-bromo-β-ketophenethylamine	Psychedelic, stimulant, entactogen and euphoriant
2C-C				OCH₃		Cl	OCH₃	2,5-dimethoxy-4-chlorophenethylamine	Psychedelic
2C-F				OCH₃		F	OCH₃	2,5-dimethoxy-4-fluoro phenethylamine	Psychedelic
2C-I				OCH₃		I	OCH₃	2,5-dimethoxy-4-iodophenethylamine	Psychedelic, stimulant
2C-D				OCH₃		CH₃	OCH₃	2,5-dimethoxy-4-methylphenethylamine	Psychedelic, stimulant
2C-E				OCH₃		CH₂-CH₃	OCH₃	2,5-dimethoxy-4-ethylphenethylamine	Psychedelic
2C-P				OCH₃		CH₂-CH₃-CH₃	OCH₃	2,5-dimethoxy-4-propylphenethylamine	Entactogen, euphoriant and Psychedelic
2C-N				OCH₃		NO₂	OCH₃	2,5-dimethoxy-4-nitrophenethylamine	euphoriant
2C-T-2				OCH₃		S-CH₂CH₃	OCH₃	2,5-dimethoxy-4-ethylthio-phenethylamine	Psychedelic
2C-T-4				OCH₃		S-CH(CH₃)₂	OCH₃	2,5-dimethoxy-4-isopropyl thio-phenethylamine	Psychedelic
2C-T-7				OCH₃		S-CH₂CH₂CH₃	OCH₃	2,5-dimethoxy-4-propylthio-phenethylamine	Psychedelic
2C-T-8				OCH₃		S-CH₂-C₃H₅	OCH₃	2,5-dimethoxy-4-cyclopropyl methylthio-phenethylamine	Psychedelic
2C-T-19				OCH₃		S-C(CH₃)₃	OCH₃	2,5-dimethoxy-4-tert-butylthio-phenethylamine	Psychedelic
2C-T-21				OCH₃		S-CH₂-CH₂-F	OCH₃	2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine	Psychedelic and euphoriant
25B-NBOMe ^[3]	CH₂-C₆H₄-OCH₃			OCH₃		Br	OCH₃	2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25C-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		Cl	OCH₃	2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25F-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		F	OCH₃	2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25I-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		I	OCH₃	2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25D-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		CH₂	OCH₃	2-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25E-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		CH₂-CH₃	OCH₃	2-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
25P-NBOMe	CH₂-C₆H₄-OCH₃			OCH₃		CH₂-CH₃-CH₃	OCH₃	2-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine	Psychedelic
Mescaline-NBOMe	CH₂-C₆H₄-OCH₃				OCH₃	OCH₃	OCH₃	N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine	Psychedelic
25B-NBOH	CH₂–C₆H₄–OH			OCH₃		Br	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine	Psychedelic
25C-NBOH	CH₂–C₆H₄–OH			OCH₃		Cl	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine	Psychedelic
25I-NBOH	CH₂–C₆H₄–OH			OCH₃		I	OCH₃	N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine	Psychedelic
25I-NBF	CH₂–C₆H₄–F			OCH₃		I	OCH₃	N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine	Psychedelic
Short Name	R^N	R^α	R^β	R²	R³	R⁴	R⁵	Full Name	Biologic activity

Detection

method	Requirement
UV spectrometry	Reagent needed

Notes

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

Related Research Articles

Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.

<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> 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.

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

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">Methedrone</span> Chemical compound of the cathinone class

Methedrone is a recreational drug of the cathinone chemical class. Chemically, methedrone is closely related to para-methoxymethamphetamine (PMMA), methylone and mephedrone. Methedrone received media attention in 2009 after the death of two young Swedish men. In both cases toxicology analysis showed methedrone was the only drug present in both men during the time of their overdose and subsequent deaths.

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.

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<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-HT_2A, 5-HT_2B, and 5-HT_2C 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.

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 (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.

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.

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-HT_2A 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-HT_2A 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

↑ 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.
↑ 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.
↑ 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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[1] In other words, all of the compounds that belong to this class are structural analogs of phenethylamine.

[4] Two ethyl groups attached to the amine group

[2] 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.

[3] 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.

[5] 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.

[note 1]

[1]

[2]

[note 2]

[3]

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine