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Substituted phenethylamine
Drug class
Thestructural formula ofphenethylamine 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

Substituted phenethylamines (or simplyphenethylamines) are achemical class oforganic compounds that are based upon thephenethylamine structure;^{[note 1]} the class is composed of all thederivative compounds of phenethylamine which can be formed by replacing, orsubstituting, one or morehydrogen atoms in the phenethylamine core structure withsubstituents. Phenylethylamines are also generally found to becentral nervous system stimulants with many also being entactogens/empathogens, and hallucinogens.

Thestructural formula of any substituted phenethylamine contains aphenyl ring that is joined to anamino (NH) group via a two-carbonsidechain. Hence, any substituted phenethylamine can be classified according to the substitution ofhydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with aspecific group of atoms. Several classes of substances can be considered phenylethylamine derivatives such asSubstituted amphetamines, where there is amethyl group substituted at the alpha position on the ethyl chain,Substituted methylenedioxyphenethylamines, where amethylenedioxy group is joined at the 3 and 4 positions on the phenyl ring, andSubstituted cathinones, which have a carbonyl group substituted at the beta position on the ethyl chain, most of which also have a methyl group substituted at the alpha positioning making most cathinones substituted amphetamines as well.

Most substituted phenethylamines arepsychoactive drugs which belong to a variety of differentdrug classes, includingcentral nervous systemstimulants (e.g.,amphetamine),hallucinogens (e.g.,3,4,5-trimethoxyphenethylamine a.k.a. mescaline,2,5-dimethoxy-4-methylamphetaminea.k.a. DOM),entactogen (e.g. MDA),appetite suppressants (e.g.phentermine),nasal decongestants andbronchodilators (e.g.,levomethamphetamine andpseudoephedrine),antidepressants (e.g.bupropion andphenelzine),antiparkinson agents (e.g.,selegiline), andvasopressors (e.g.,ephedrine), among others.^[1][2] Many of these psychoactive compounds exert their pharmacological effects primarily by modulatingmonoamine neurotransmitter systems; however, there is no knownmechanism of action orbiological target that is common to all members of this subclass.^{[medical citation needed]}

Numerousendogenous compounds – includinghormones,catecholamines such asdopamine andnoradrenaline, and manytrace amines (e.g.adrenaline,phenethylamine itself,tyramine,thyronamine, andiodothyronamine) – are substituted phenethylamines. Several notablerecreational drugs, such asMDPV (Monkey Dust),MDMA (ecstasy),methamphetamine, andcathinone, are also members of the class. Many well-known prescription drugs are from the phenylethylamine class such asAdderall which usesAmphetamine, Desoxyn which uses methamphetamine, and Sudafed which usespseudoephedrine.

Selected Phenethylamines

Structure	Short Name	RN	Rα	Rβ	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-methylphenethylamine	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 aminergicα-adrenoceptor agonist
	Oxidopamine				OH		OH	OH	2,4,5-trihydroxyphenethylamine	neurotoxic agent for thedopamine andnorepinephrine 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-isopropylphenethylamine	β-adrenergic agonist;decongestant
	Salbutamol	C(CH3)3		OH		CH2OH	OH		β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine	Short-actionβ2-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 afood 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 selectivemonoamine 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 selectivenorepinephrine releasing agent
	Cathinone		CH3	=O					β-ketoamphetamine	Selectivenorepinephrine anddopamine releasing agent
	Methcathinone	CH3	CH3	=O					N-methylcathinone	Selectivenorepinephrine anddopamine 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, andreleasing agent
	MDMA	CH3	CH3			-O-CH2-O-			3,4-methylenedioxy-N-methylamphetamine	Psychedelic,entactogen, andreleasing agent
	MDMC	CH3	CH3	=O		-O-CH2-O-			3,4-methylenedioxymethcathinone	Psychedelic,entactogen, andreleasing agent
	MMDA		CH3			-O-CH2-O-		OCH3	5-methoxy-3,4-methylenedioxy-amphetamine	Stimulant,psychedelic andentactogen
	MMDMA	CH3	CH3			-O-CH2-O-		OCH3	5-methoxy-3,4-methylenedioxy-N-methylamphetamine	Psychedelic,entactogen, andreleasing agent
	Lophophine					-O-CH2-O-		OCH3	5-methoxy-3,4-methylenedioxyphenethylamine	Psychedelic andentactogen
	Mescaline					OCH3	OCH3	OCH3	3,4,5-trimethoxyphenethylamine	Psychedelic andentactogen
	Proscaline					OCH3	OCH2CH2CH3	OCH3	2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine	Psychedelic andentactogen
	Metaescaline					OCH2CH3	OCH3	OCH3	2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine	Psychedelic andentactogen
	Allylescaline					OCH3	OCH2CH1CH2	OCH3	4-Allyloxy-3,5-dimethyloxyphenylethylamine	Psychedelic andentactogen
	Methallylescaline					OCH3	OCH2C(CH2CH3)	OCH3	4-Methallyloxy-3,5-dimethoxyphenethylamine	Psychedelic andentactogen
	Asymbescaline					OCH2CH3	OCH2CH3	OCH3	3,4-Diethoxy-5-methoxyphenethylamine	Psychedelic andeuphoriant
	DOM		CH3		OCH3		CH3	OCH3	2,5-dimethoxy-4-methylamphetamine	Psychedelic
	DOB		CH3		OCH3		Br	OCH3	2,5-dimethoxy-4-bromoamphetamine	Psychedelic
	DOC		CH3		OCH3		Cl	OCH3	2,5-dimethoxy-4-chloroamphetamine	Psychedelic
	DOI		CH3		OCH3		I	OCH3	2,5-dimethoxy-4-iodoamphetamine	Psychedelic
	DON		CH3		OCH3		NO2	OCH3	2,5-dimethoxy-4-nitroamphetamine	Stimulant
	2C-B				OCH3		Br	OCH3	2,5-dimethoxy-4-bromophenethylamine	Psychedelic,stimulant,entactogen andeuphoriant
	βk-2C-B			=O	OCH3		Br	OCH3	2,5-dimethoxy-4-bromo-β-ketophenethylamine	Psychedelic,stimulant,entactogen andeuphoriant
	2C-C				OCH3		Cl	OCH3	2,5-dimethoxy-4-chlorophenethylamine	Psychedelic
	2C-F				OCH3		F	OCH3	2,5-dimethoxy-4-fluorophenethylamine	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-O-4				OCH3		(CH3)2CHO	OCH3	2,5-Dimethoxy-4-propoxyphenethylamine	Hallucinogen,psychedelic andentheogenic[3]
	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-isopropylthio-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-cyclopropylmethylthio-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 andeuphoriant
	25B-NBOMe[4]	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	RN	Rα	Rβ	R2	R3	R4	R5	Full Name	Biologic activity

This sectionneeds expansion. You can help byadding to it.(December 2015)

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 likegas chromatography-mass spectrometry (GC-MS),liquid chromatography-mass spectrometry (LC-MS), and immunoassay screenings are commonly employed for accurate identification. Advanced methods likehigh-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.^{[citation needed]}

There are manycyclized phenethylamines. Examples include the following:

• Phenylalkylpyrrolidines likePEP,MPEP,prolintane,α-PPP,α-PVP,pyrovalerone, andMDPV
• Tetrahydroisoquinolines likeanhalinine,pellotine,lophophorine,DOM-CR,nomifensine,tetrabenazine, andzelandopam
• Isoquinolines likeperafensine,quinisocaine, andtilisolol
• Dihydroindoles andaminochromes likeadrenochrome andadrenolutin
• 2-Aminoindanes like2-aminoindane,MDAI,MMAI,DOM-AI, andPyr-AI
• 2-Aminotetralins like2-aminotetralin,MDAT,DOM-AT,8-OH-DPAT, androtigotine
• 1-Aminomethylindanes like2CB-Ind,AMMI,jimscaline, andbromojimscaline
• 3-Benzazepines likefenoldopam andlorcaserin
• Benzocyclobutenes like2CBCB-NBOMe,S33005,TCB-2,tomscaline, andbromotomscaline
• Tetrahydrobenzopyranylamines likeCT-5126
• Benzoxepins likeTFMBOX
• 2-Benzylpiperidines andphenidates like2-benzylpiperidine andmethylphenidate
• Phenylcyclopropylamines liketranylcypromine,TMT, andDMCPA
• 3-Phenylpiperidines like3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48, andZ3517967757 (Z7757)
• 2-Phenylmorpholines like2-phenylmorpholine,phenmetrazine,manifaxine,radafaxine,flumexadol,oxaflozane, andPF-219,061
• Phenyloxazolamines oraminorex analogues likeaminorex andpemoline
• Tricyclic compounds likebenzoctamine anddizocilpine
• Ergolines andlysergamides likeergine (LSA) andLSD
• Partial ergolines and lysergamides likeNDTDI,RU-27849,DEIMDHPCA, andDEMPDHPCA
• Pyridopyrroloquinoxalines likelumateperone,IHCH-7113,IHCH-7086, andITI-1549
• Others like6-AB,2-ADN,2C-B-PYR,2C-B-5-hemiFLY-α6 (BNAP),2CB7 (2C-B-5-hemiFLY-β7),2CBecca,2CJP,2CLisaB,2CLisaH,2-naphthylamine,GYKI-52895,ivabradine,milnacipran,Org 6582,rimiterol, andZC-B

Some additional cyclized phenethylamines have also been described.^[5][6][7]

Other related families that are not phenethylamines themselves includephenylpiperazines,benzylpiperazines, and4-phenylpiperidines.

• Substituted amphetamine
• Substituted methylenedioxyphenethylamine
• Substituted cathinone
• Substituted phenylmorpholine
• Substituted methoxyphenethylamine
• 2C,DOx,4C,Ψ-PEA,scaline,3C,25-NB,FLY
• Substituted tryptamine
• PiHKAL
• The Shulgin Index

• Phenethylamines
• Chemical classes of psychoactive drugs

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