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Class of compounds based upon the β-hydroxyamphetamine structure
Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as phenylisopropanolamines, phenylpropanolamines, norephedrines, or cathinols
Substituted β-hydroxyamphetamine
Substituted_β-hydroxyamphetamine
Index of chemical compounds with the same name
Gepefrine (3-hydroxyamphetamine) 4-Hydroxyamphetamine N-Hydroxyamphetamine Hydroxymethylamphetamine Substituted β-hydroxyamphetamine This set index
Hydroxyamphetamine
Group of stereoisomers
substituted phenethylamine and amphetamine. Hydroxyamphetamine appeared to remain marketed only in the Czech Republic as of 2004. Hydroxyamphetamine is
4-Hydroxyamphetamine
Pharmaceutical compound
N-Hydroxyamphetamine (NOHA), also known as AMPH-OH, is a stimulant drug of the amphetamine family. It is the N-hydroxy derivative of amphetamine and has
N-Hydroxyamphetamine
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
DOx
Class of compounds based upon the amphetamine structure
(PTSD). Substituted phenethylamines Substituted β-hydroxyamphetamines Substituted methylenedioxyphenethylamines Substituted cathinones Substituted phenylmorpholines
Substituted_amphetamine
Chemical class of organic compounds
derivatives such as Substituted amphetamines, where there is a methyl group substituted at the alpha position on the ethyl chain, Substituted methylenedioxyphenethylamines
Substituted_phenethylamine
Index of chemical compounds with the same name
N-Hydroxymethamphetamine (N-hydroxy-N-methylamphetamine) Hydroxyamphetamine Substituted β-hydroxyamphetamine Elks, J. (2014). The Dictionary of Drugs: Chemical
Hydroxymethylamphetamine
Class of chemical compounds
(tranquilizer) Substituted α-alkyltryptamine Substituted amphetamine Substituted cathinone Substituted methylenedioxyphenethylamine Substituted phenethylamine
Substituted_piperazine
Class of indoles
Substituted 2-aminoindane Substituted amphetamine Substituted benzofuran Substituted cathinone Substituted methylenedioxyphenethylamine Substituted phenethylamine
Substituted_tryptamine
Chemical compound
concentrations on 4-hydroxyamphetamine metabolism in humans suggests that a different enzyme may mediate the conversion of 4-hydroxyamphetamine to 4-hydroxynorephedrine;
Phenylacetone
Pharmaceutical compound
monoamine release in the HEK293 system have been reported. Substituted β-hydroxyamphetamine Mayer FP, Cintulova D, Pittrich DA, Wimmer L, Luethi D, Holy
4-Methylephedrine
Sympathomimetic drug in the amphetamine family
also known as 3-hydroxy-α-methylphenethylamine or as 3-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. It is used pharmaceutically
Gepefrine
Sympathomimetic agent
2SR)-α-methyl-β-hydroxyphenethylamine or as (1RS,2SR)-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. It is closely
Phenylpropanolamine
Chemical compound
5-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,5-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. Analogues of methoxamine
Methoxamine
Class of chemical compounds
structure Substituted amphetamines Substituted β-hydroxyamphetamines Substituted methylenedioxyphenethylamines Substituted phenethylamines Substituted phenylmorpholines
Substituted_cathinone
Psychedelic and entactogen
controlled substance in the United States. Substituted methylenedioxyphenethylamine HOT-x (psychedelics) N-Hydroxyamphetamine N-Hydroxy-DOM N-Hydroxy-AMT Shulgin
3,4-Methylenedioxy-N-hydroxyamphetamine
3,4-Methylenedioxy-N-hydroxyamphetamine
Pharmaceutical compound
known metabolite of the stimulant drug methamphetamine. Substituted amphetamine N-Hydroxyamphetamine MDMOH (FLEA) Abbruscato TJ, Trippier PC (October 2018)
N-Hydroxymethamphetamine
Group of chemical compounds
Substituted isotryptamines, or simply isotryptamines, also known as 2-(1-indolyl)ethylamines, are a group of indoles closely related to the tryptamines
Substituted_isotryptamine
Pharmaceutical drug
names (Onsukil, Masacin, Procadil and others). Substituted phenylisobutylamine Substituted β-hydroxyamphetamine Eldon MA, Battle MM, Coon MJ, Nordblom GD,
Procaterol
Chemical compound
and sigma receptors. Chemically, ifenprodil is a substituted phenethylamine and β-hydroxyamphetamine derivative. It is used pharmaceutically as the tartrate
Ifenprodil
Class of psychoactive drugs
amphetamine Substituted benzofuran Substituted benzothiophene Substituted cathinone Substituted phenethylamine Substituted phenylmorpholine Substituted tryptamine
Substituted methylenedioxyphenethylamine
Substituted_methylenedioxyphenethylamine
Class of chemical compounds
among others. Cyclized phenethylamine Substituted methylenedioxyphenethylamine (MDxx) Substituted benzofuran Substituted α-alkyltryptamine Borax combo Sainsbury
Substituted_2-aminoindane
Anti-ulcer drug
The drug is orally active. Structurally, trecadrine is a substituted β-hydroxyamphetamine and derivative of β-hydroxy-N-methylamphetamine (ephedrine
Trecadrine
Chemical compound
metabolite of amphetamine, it is produced from both p-hydroxyamphetamine and norephedrine. 4-Hydroxyamphetamine has been shown to be metabolized into 4-hydroxynorephedrine
P-Hydroxynorephedrine
Class of chemical compounds
A scaline, also known as a substituted mescaline analogue and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of
Scaline
Analogue of ephedrine and a norepinephrine releasing agent
4-Fluoroephedrine (4-FEP) is a "novel psychoactive substance" and substituted β-hydroxyamphetamine derivative related to ephedrine. Similarly to other amphetamines
4-Fluoroephedrine
Class of chemical compounds
3C (3C-x), also known as 4-substituted 3,5-dimethoxyamphetamines, substituted 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1) analogues, or 3C-scalines
3C_(psychedelics)
Class of chemical compounds
Substituted phenethylamine Substituted amphetamine Substituted cathinone Substituted methylenedioxyphenethylamine Substituted benzofuran Substituted 2-aminoindane
Substituted naphthylethylamine
Substituted_naphthylethylamine
Berefrine RO5166017 List of methylphenidate analogues Substituted benzofuran Substituted cathinone Substituted phenylmorpholine Meschino JA, Poos GI. 2-amino-5
List_of_aminorex_analogues
Index of chemical compounds with the same name
Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines
Cycloalkylaminopropane
Index of chemical compounds with the same name
6-Tetramethoxyamphetamine (TeMA-2) 2,3,5,6-Tetramethoxyamphetamine (TeMA-3) Substituted methoxyphenethylamine Methoxyamphetamine Dimethoxyamphetamine Trimethoxyamphetamine
Tetramethoxyamphetamine
Class of chemical compounds
Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines
1,2-Diarylethylamine
Group of psychedelic drugs
phenethylamine blanket-ban language. 2C (psychedelics) Substituted methoxyphenethylamine N-Hydroxyamphetamine MDOH (MDH; N-OH-MDA) MDHMA (FLEA; N-OH-MDMA) 2C-B-OH
HOT-x
Central nervous system stimulant prodrug
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Lisdexamfetamine
Class of chemical compounds
ASR-2001 (2CB-5PrO)) Scalines (4-substituted 3,5-DMPEAs) (e.g., 4-desoxymescaline (DESOXY; 4-Me-3,5-DMPEA)) Ψ-PEAs (4-substituted 2,6-DMPEAs) (e.g., Ψ-2C-T-4)
Substituted methoxyphenethylamine
Substituted_methoxyphenethylamine
Pharmaceutical compound
DOOH, also known as 2,5-dimethoxy-4-hydroxyamphetamine, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to the psychedelic
2,5-Dimethoxy-4-hydroxyamphetamine
2,5-Dimethoxy-4-hydroxyamphetamine
Class of chemical compounds
Lizard Labs in the 2010s and 2020s. Substituted ergoline Partial lysergamide Substituted tryptamine Substituted phenethylamine Lizard Labs Jamieson CS
Lysergamides
Class of chemical compounds
effects. The Simple Plant Isoquinolines (2002) Substituted phenethylamine Substituted 3-benzazepine Substituted β-carboline and harmala alkaloid Iboga-type
Substituted tetrahydroisoquinoline
Substituted_tetrahydroisoquinoline
Methaqualone and Beyond: Structure–Activity Relationship of 6-, 7-, and 8-Substituted 2,3-Diphenyl-quinazolin-4(3 H )-ones and in Silico Prediction of Putative
List of methaqualone analogues
List_of_methaqualone_analogues
Index of chemical compounds with the same name
6-Dimethoxyamphetamine (2,6-DMA; DMA-5) 3,5-Dimethoxyamphetamine (3,5-DMA; DMA-6) Substituted methoxyphenethylamine Methoxyamphetamine Trimethoxyamphetamine Tetramethoxyamphetamine
Dimethoxyamphetamine
Chemical compound
β-trihydroxy-N-methylamphetamine), and hydroxyamphetamine (norpholedrine; α-methyltyramine; 4-hydroxyamphetamine) Substituted amphetamine 3,4-Dihydroxymethamphetamine
Α-Methyldopamine
Class of chemical compounds
4C (4C-x), also known as 4-substituted 2,5-dimethoxy-α-ethylphenethylamines, is a general name for the family of psychedelic and related phenylisobutylamines
4C_(psychedelics)
is a tricyclic chemical compound. Derivatives of dibenzodiazepine, or substituted dibenzodiazepines, include the antipsychotic clozapine, the antihistamine
Dibenzodiazepine
Serotonin receptor agonist
prodrug of norpsilocin. 4-HT, also known as 4-hydroxytryptamine, is a substituted tryptamine derivative. It is a positional isomer of the neurotransmitter
4-Hydroxytryptamine
Index of chemical compounds with the same name
6-TMA; TMA-5) 2,4,6-Trimethoxyamphetamine (2,4,6-TMA; TMA-6; ψ-TMA-2) Substituted methoxyphenethylamine Methoxyamphetamine Dimethoxyamphetamine Tetramethoxyamphetamine
Trimethoxyamphetamine
Monoamine neurotransmitter
Some serotonergic psychedelics, like psilocin, DMT, and 5-MeO-DMT, are substituted tryptamines and are very similar in chemical structure to serotonin.
Serotonin
Pharmaceutical compound
N-Hydroxy-DOM, also known as 4-methyl-2,5-dimethoxy-N-hydroxyamphetamine or as DOM-OH, is a possible psychedelic drug of the phenethylamine, amphetamine
N-Hydroxy-DOM
Class of chemical compounds
A substituted pyridopyrroloquinoxaline, or more specifically a substituted octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline, also known as a
Pyridopyrroloquinoxaline
Class of chemical compounds
They are positional isomers of the 4-substituted 2,5-dimethoxyphenethylamines (e.g., 2Cs and DOx) and 4-substituted 3,5-dimethoxyphenethylamines (e.g.,
Ψ-PEA
Chemical compound
behavioral sensitization and leads to excessive alcohol intake in rats. Substituted tetrahydroisoquinoline Norsalsolinol 6-Hydroxydopamine MPTP Rotenone
Salsolinol
Chemical compound
known as N-nitrosoamphetamine, is a product of the oxidation of N-hydroxyamphetamine, which is formed during the metabolism of amphetamine and methamphetamine
2-Nitroso-1-phenylpropane
Chemical compound
4-dihydroxy-N-ethylnorephedrine; α-methyl-N-ethylnorepinephrine), and hydroxyamphetamine (4-hydroxyamphetamine; α-methyltyramine). Corbadrine is the generic name of the
Corbadrine
Metabolite of bupropion
(developmental code names BW 494, BW A494U) is a substituted amphetamine derivative—specifically a β-hydroxyamphetamine—and a major active metabolite of the antidepressant
Threohydrobupropion
Class of chemical compounds
The substituted benzothiophenes are a class of chemical compounds based on benzothiophene. They are closely related to the substituted benzofurans, substituted
Substituted_benzothiophene
Class of chemical compounds
Substituted methylenedioxyphenethylamine § Related compounds Substituted 2-aminoindane Substituted amphetamine Substituted benzothiophene Substituted
Substituted_benzofuran
Class of chemical compounds
(AMDA) F (F-1; 5-methoxy-6-APDB) Substituted phenethylamine Substituted amphetamine Substituted benzofuran Substituted methoxyphenethylamine 2C, DOx, 4C
FLY_(psychedelics)
physiological pH. List of modafinil analogues List of cocaine analogues Substituted cathinone Klare H, Neudörfl JM, Brandt SD, Mischler E, Meier-Giebing
List of methylphenidate analogues
List_of_methylphenidate_analogues
Antihypotensive medication
The drug is closely related to phenylpropanolamine ((1RS,2SR)-β-hydroxyamphetamine; norephedrine), ephedrine ((1R,2S)-β-hydroxy-N-methylamphetamine)
Metaraminol
Chemical compound
A substituted β-carboline, also known as a substituted 9H-pyrido[3,4-b]indole, is a chemical compound featuring a β-carboline moiety with one or more substitutions
Substituted_β-carboline
Entactogen
if intended for human consumption. Substituted methylenedioxyphenethylamine HOT-x (psychedelics) N-Hydroxyamphetamine N-Hydroxymethamphetamine Shulgin A
3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine
3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine
Pharmaceutical compound
Prodrugs of SDA and/or related compounds have also been described. Substituted methylenedioxyphenethylamine § Related compounds List of investigational
SDA_(drug)
Chemical compound
Hughes E, Jani B, et al. (February 1995). "Pholedrine: a substitute for hydroxyamphetamine as a diagnostic eyedrop test in Horner's syndrome". Journal
Pholedrine
Class of chemical compounds
converted to epinephrine. Various stimulant drugs (such as a number of substituted amphetamines) are catecholamine analogues. Catecholamines have the distinct
Catecholamine
Class of chemical compounds
simplified ibogaine analogue, also known as a substituted 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (or simply substituted hexahydroazepinoindole), is a derivative
Ibogalog
desoxyscaline, also known as a desoxygenated scaline and a type of 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine psychedelic
Desoxyscaline
MDMA metabolite
releasing agent (SNDRA). The predicted log P of HMA is 0.6. Substituted amphetamine 4-Hydroxy-3-methoxymethamphetamine (HMMA) 3,4-Dihydroxyamphetamine
4-Hydroxy-3-methoxyamphetamine
4-Hydroxy-3-methoxyamphetamine
Chemical compound
4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine
Phenylethylpyrrolidine
Drug mixture used mainly to treat ADHD and narcolepsy
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Adderall
Pharmaceutical compound
Phenylpiperidines 4-Phenylpiperidine 2-Methyl-3-phenylpiperidine Phenmetrazine Substituted phenylmorpholine 1-Phenylpiperazine Partial ergoline SKF-89145 SKF-89626
3-Phenylpiperidine
Substituted amphetamine derivative
(developmental codes BW 287, BW 17U) is a substituted amphetamine derivative—specifically a β-hydroxyamphetamine—and a minor active metabolite of the antidepressant
Erythrohydrobupropion
Class of organic compounds
Zaytsev's rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols are eliminated easily at just above
Alcohol_(chemistry)
Family of phenethylamine psychedelics
very small role. The 2C drugs, also known as 4-substituted 2,5-dimethoxyphenethylamines, are substituted phenethylamines and can be thought of as synthetic
2C_(psychedelics)
Central nervous system stimulant
of metabolic integrity. Methamphetamine belongs to the substituted phenethylamine and substituted amphetamine chemical classes and as a drug acts as a
Methamphetamine
Class of chemical compounds
Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of 2-phenylmorpholine or of the psychostimulant drug
Substituted_phenylmorpholine
CNS stimulant and isomer of amphetamine
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Dextroamphetamine
Psychoactive research chemical
a methyl substitution at Rα. Amphetamines themselves belong to the class of alpha-methylated phenethylamines.[citation needed] Substituted amphetamines
3-Fluoroamphetamine
Central nervous system stimulant
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Amphetamine
Pharmaceutical compound
substituted for PMMA, MDMA, and MDA in rodents, suggesting that it may have entactogen-like effects. 3,4-DMA produces 3-methoxy-4-hydroxyamphetamine (MHA)
3,4-Dimethoxyamphetamine
Chemical compound
addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring or a substituted phenylmorpholine. Phenmetrazine has been
Phenmetrazine
Group of alkaloids related to Tabernanthe iboga
iboga-type alkaloids include ibogamine, ibogaine, tabernanthine, and other substituted ibogamines . Ibogaine is a hallucinogen and is referred to as an oneirogen
Iboga-type_alkaloid
Serotonergic neurotoxin
4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine
2,4-Dichloroamphetamine
Weight loss medication
stimulant, rewarding, and appetite suppressant effects. Chemically, it is a substituted amphetamine. Phentermine was approved for medical use in the United States
Phentermine
Chemical compound
scientific literature, the term ‘substituted 9,10-dihydroergolines’ has sometimes been used; most often, the substitution was understood to refer to the
Ergoline
Chemical compound
Faigl F (2004). "Convenient, Benign and Scalable Synthesis of 2- and 4-Substituted Benzylpiperidines". European Journal of Organic Chemistry. 2004 (17):
2-Benzylpiperidine
One of four stable isomers of butanediol
Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines
1,4-Butanediol
Group of psychoactive drugs
The substituted ethylenedioxyphenethylamines (EDxx) are a small group of psychoactive drugs of the phenethylamine family related to the substituted
Substituted ethylenedioxyphenethylamine
Substituted_ethylenedioxyphenethylamine
Chemical compound
a substituted phenethylamine and β-hydroxyamphetamine derivative. List of investigational antidepressants Ifenprodil (another β-hydroxyamphetamine NMDA
Traxoprodil
Pharmaceutical compound
in the scientific literature, in a conference presentation, by 2024. Substituted methylenedioxyphenethylamine Cyclized phenethylamine List of investigational
APA-01
Chemical compound
Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine 3-HED 4-Hydroxyamphetamine 4-ME Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Lomardexamfetamine
1-Aminomethylindane
Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine 3-HED 4-Hydroxyamphetamine 4-ME Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Lomardexamfetamine
Phenylcyclopropylamine
Class of chemical compounds
Substituted arylalkylamines, also alternatively known in many cases as substituted arylethylamines, are a group of chemical compounds. These compounds
Arylalkylamine
Chemical compound
PAL-594) is a recreational designer drug with stimulant effects. It is a substituted phenylmorpholine derivative, closely related to better known drugs such
3-Chlorophenmetrazine
Tian S, Shui W, Ye N (February 2020). "Identification of Novel 1-O-Substituted Aporphine Analogues as Potent 5-HT2C Receptor Agonists". ACS Chem Neurosci
Noraporphine
Class of chemical compounds
(disambiguation) Seco-LSD Secoergoline Des-LSD Substituted lysergamide Substituted tryptamine Substituted phenethylamine Basargin AG, Domokosa A, Hennessey
Partial_lysergamide
Class of chemical compounds
doses. Benzazepine Cyclized phenethylamine Substituted tetrahydroisoquinoline Ibogalog Iboga alkaloid Substituted β-carboline Kawase M, Saito S, Motohashi
Substituted_3-benzazepine
Drug that stimulates a response from the adrenergic receptors
atomoxetine, cocaine, and some amphetamine based stimulants such as 4-hydroxyamphetamine. Ephedrine Pseudoephedrine Droxidopa or L-DOPS L-DOPA Adrenergic receptor
Adrenergic_agonist
Index of chemical compounds with the same name
N-Alkylamphetamine, or a substituted N-alkylamphetamine, is an amphetamine with an alkyl group at the amine nitrogen and can refer to: N-Methylamphetamine
N-Alkylamphetamine
Pharmaceutical compound
(MPAP) is the 3,4-methylenedioxy derivative of PPAP. Substituted phenethylamine N,α-Diethylphenethylamine (DEPEA) β-Methylphenethylamine
Α-Propylphenethylamine
Family of serotonergic psychedelics
including: Substituted methoxyphenethylamine 4-Substituted 2,5-dimethoxyphenethylamines (2Cs) 4-Substituted 2,5-dimethoxyamphetamines (DOx) 4-Substituted 2
25-NB
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SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
SUBSTITUTED HYDROXYAMPHETAMINE
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