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Group of stereoisomers
Hydroxyamphetamine, also known as 4-hydroxyamphetamine or norpholedrine and sold under the brand names Paredrine and Paremyd among others, is a sympathomimetic
4-Hydroxyamphetamine
Index of chemical compounds with the same name
Gepefrine (3-hydroxyamphetamine) 4-Hydroxyamphetamine N-Hydroxyamphetamine Hydroxymethylamphetamine Substituted β-hydroxyamphetamine This set index
Hydroxyamphetamine
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
Central nervous system stimulant
metabolites are amphetamine and 4-hydroxymethamphetamine; other minor metabolites include: 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone,
Methamphetamine
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
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
Central nervous system stimulant prodrug
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Lisdexamfetamine
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
Chemical compound found in some species of mushrooms
Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), is a naturally occurring tryptamine alkaloid and investigational drug found
Psilocybin
Psychedelic drug
Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families
Psilocin
Central nervous system stimulant
para-hydroxyamphetamine (pOH-AMP), 4 (phenylacetone), N-hydroxyamphetamine, and norephedrine (Figure 1).31 "Compound Summary". p-Hydroxyamphetamine. PubChem
Amphetamine
Chemical compound
DBH, and CYP2D6. Human monoamine oxidase enzymes metabolize tyramine into 4-hydroxyphenylacetaldehyde. If monoamine metabolism is compromised by the use
Tyramine
Psychoactive drug, often called ecstasy
3,4-methylenedioxyphenylacetone (MDP2P), and 3,4-methylenedioxy-N-hydroxyamphetamine (MDOH). The contributions of these metabolites to the psychoactive
MDMA
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
Chemical compound
amphetamine. The primary psychological effects have a duration of roughly 3 to 4 hours, with aftereffects such as tachycardia, hypertension, and mild stimulation
Methylenedioxypyrovalerone
Recreational drug
Mephedrone, also known as 4-methylmethcathinone, 4-MMC, or 4-methylephedrone, is a synthetic stimulant drug belonging to the amphetamine and cathinone
Mephedrone
Psychedelic and entactogen
3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA, is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine
3,4-Methylenedioxy-N-hydroxyamphetamine
3,4-Methylenedioxy-N-hydroxyamphetamine
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
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
4-Fluoroephedrine
Sympathomimetic agent
usually a racemic mixture of the (1R,2S)- and (1S,2R)-enantiomers of β-hydroxyamphetamine and is also known as dl-norephedrine. Phenylpropanolamine was first
Phenylpropanolamine
Chemical compound
Methylhexanamine is synthesized by reacting 4-methylhexan-2-one with hydroxylamine, which converts the 4-methylhexan-2-one to 4-methylhexan-2-one oxime, which is
Methylhexanamine
MDMA metabolite
4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-O-methyl-α-methyldopamine, is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA).
4-Hydroxy-3-methoxyamphetamine
4-Hydroxy-3-methoxyamphetamine
Psychedelic drug
4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin, is a psychedelic drug of the tryptamine family
4-AcO-DMT
Substituted cathinone designer drug
releasing activity. 3-Methylmethcathinone is a structural isomer of mephedrone (4-methylmethcathinone), and as such is illegal via blanket bans in many countries
3-Methylmethcathinone
Drug class
especially cytochrome P450 2D6, producing metabolites including 4-hydroxyamphetamine, 4 hydroxynorephedrine, hippuric acid, benzoic acid and benzyl methyl
Norepinephrine–dopamine releasing agent
Norepinephrine–dopamine_releasing_agent
Chemical compound
from the inactive metabolite phenylacetone. 4-Hydroxyamphetamine has been shown to be metabolized into 4-hydroxynorephedrine by dopamine beta-hydroxylase
4-Hydroxyphenylacetone
Pharmaceutical compound
putative stimulant drug of the phenethylamine, amphetamine, and β-hydroxyamphetamine families. It is the β-hydroxy analogue of mephedrone and is a known
4-Methylephedrine
Entactogen, stimulant, and psychedelic drug of the amphetamine family
Consciousness. Pantheon Books. pp. 26–77. ISBN 978-0-394-48826-4. Yensen R (1975). The Use of 3, 4 Methylenedioxyamphetamine (MDA) as an Adjunct to Brief Intensive
3,4-Methylenedioxyamphetamine
Topical nasal decongestant
levels of levomethamphetamine range from 3.3 to 31.4 ng/mL with single oral doses of 1 to 10 mg and from 65.4 to 125.9 ng/mL with single intravenous doses of
Levomethamphetamine
Metabolite of the amino acid tryptophan
tryptophan to tryptamine. Tryptamine is a ligand for gut epithelial serotonin type 4 (5-HT4) receptors and regulates gastrointestinal electrolyte balance through
Tryptamine
Class of psychoactive drugs that produce empathic experiences
includes stimulants like dextroamphetamine and psychedelics like 2,5-dimethoxy-4-methylamphetamine), which makes MDMA a substituted phenethylamine (which includes
Entactogen
Codrug of amphetamine and theophylline
Retrieved 3 February 2016. "The Arab World's New Drug of Choice". BBC Radio 4. 4 June 2022. Chulov M (7 May 2021). "'A dirty business': how one drug is turning
Fenethylline
Weight loss medication
methamphetamine (N-methylamphetamine) and of other methylamphetamines such as 4-methylamphetamine. A number of derivatives of phentermine exist, including
Phentermine
CNS stimulant and isomer of amphetamine
dextroamphetamine are metabolized via CYP2D6-mediated hydroxylation to produce 4-hydroxyamphetamine and additionally via oxidative deamination. There are several enzymes
Levoamphetamine
Chemical compound
it is produced from both p-hydroxyamphetamine and norephedrine. 4-Hydroxyamphetamine has been shown to be metabolized into 4-hydroxynorephedrine by dopamine
P-Hydroxynorephedrine
Medication used to treat dyskinesia
recommending the use of amantadine (100–200 mg b.i.d.) for adults with DoC 4 to 16 weeks after injury to support early functional recovery and reduce disability
Amantadine
Pharmaceutical compound
2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and other phrases), is a psychedelic drug
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine
Entactogen drug
O-methylation of the 3- or 4-hydroxy group to 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). Another metabolite
Methylone
Organic compound, a stimulant in humans
dioxide to form a solid carbonate salt. Phenethylamine is strongly basic, pKb = 4.17 (or pKa = 9.83), as measured using the HCl salt, and forms a stable crystalline
Phenethylamine
Pharmaceutical compound
4-(2-Aminopropyl)benzofuran (4-APB) is a monoamine releasing agent and novel designer drug of the benzofuran family. It acts as a serotonin–norepinephrine–dopamine
4-APB
Chemical compound
1,3-Dimethylbutylamine (1,3-DMBA, dimethylbutylamine, DMBA, 4-amino-2-methylpentane, or AMP), is a stimulant drug structurally related to methylhexanamine
1,3-Dimethylbutylamine
Pharmaceutical compound
Phenylbutenamine, or 4-phenylbut-3-en-2-amine, is a monoamine releasing agent (MRA) of the arylalkylamine family related to β-phenethylamine and amphetamine
Phenylbutenamine
Topical nasal decongestant
hours for adults and children 6–12 years of age. Each inhalation delivers 0.4 to 0.5 mg (400 to 500 μg) in 800 mL of air. Use is not to exceed three days
Propylhexedrine
Pharmaceutical compound
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
1,4-Dimethylamylamine
Medication
depressive symptom improvement (SMD = −1.49, k = 6, n = 282 vs. SMD = −0.27, k = 4, n = 1,026, respectively; p = 0.03). However, this was largely due to older
Selegiline
Pharmaceutical compound
was first described in the scientific literature by 2012. 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP; PAL-179) Rothman RB, Partilla JS, Baumann
Para-Nitrophenylpiperazine
Psychedelic drug
analog of other psychedelic tryptamines such as 4-AcO-DMT (O-acetylpsilocin), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), O-methylbufotenin (5-MeO-DMT), and
Dimethyltryptamine
Chemical compound
cathinone in blood plasma is reached. The mean residence time is 5.2 ± 3.4 hours. The elimination half-life of cathinone is 1.5 ± 0.8 hours. A two-compartment
Cathinone
Serotonin-norepinephrine-dopamine reuptake inhibitor
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
Centanafadine
Organic compound involved in immune responses
physiological conditions, the aliphatic amino group (having a pKa around 9.4) will be protonated, whereas the second nitrogen of the imidazole ring (pKa
Histamine
Chemical compound
5-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,5-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. Analogues
Methoxamine
Chemical compound
4-Benzylpiperidine is a drug and research chemical used in scientific studies. It has been encountered as a designer drug. 4-Benzylpiperidine acts as a
4-Benzylpiperidine
Psychoactive stimulant
Evaluation of Rigid Analogues of Methamphetamines". ScholarWorks@UNO. Retrieved 4 November 2024. Blough B (July 2008). "Dopamine-releasing agents" (PDF). In
Methcathinone
Chemical compound
adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research. 4 (2): 147–150. CiteSeerX 10.1.1.688.3796. doi:10.1080/10298420290015827. eISSN 1476-3524
Adrenochrome
Stimulant designer drug of the substituted cathinone class
closely related to better known drugs such as 3-methylmethcathinone and 4-methylmethcathinone (mephedrone). It was first identified in Sweden in 2014
2-Methylmethcathinone
Chemical compound
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
Indanorex
Psychedelic drug
2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by names such as Nexus or Erox, is a psychedelic drug of the phenethylamine and 2C families
2C-B
Monoamine neurotransmitter
5-hydroxyindoleacetic acid". The American Journal of Clinical Nutrition. 42 (4): 639–643. doi:10.1093/ajcn/42.4.639. PMID 2413754. González-Flores D, Velardo B, Garrido M
Serotonin
Medication, stimulant and decongestant
doses from 60 mg to 150mg, with or without caffeine, for 4 to 24 weeks led to a 2 kilograms (4.4 lb) weight loss greater than placebo, raised heart rate
Ephedrine
Chemical compound
Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine
Para-Methoxy-N-ethylamphetamine
Para-Methoxy-N-ethylamphetamine
Class of chemical compounds
Melbourne: Cengage. p. 143. ISBN 978-0-17-035484-4. "Catecholamines in Urine". webmd.com. Retrieved 4 May 2017. Kuklin, A. I.; Conger, B. V. (1995). "Catecholamines
Catecholamine
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
Organic chemical that functions both as a hormone and a neurotransmitter
algal blooms, dopamine is present in very high concentrations, estimated at 4.4% of dry weight. There is evidence that this dopamine functions as an anti-herbivore
Dopamine
Chemical compound responsible for rotten fish odor
Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4. Swift, Elijah; Hochanadel, Helen Phillips (May 1945). "The Vapor Pressure
Trimethylamine
Pharmaceutical compound
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
Octodrine
Pharmaceutical compound
Phenylbutynamine (4-phenylbut-3-yn-2-amine; development code PAL-874) is a monoamine releasing agent (MRA) of the arylalkylamine family related to β-phenethylamine
Phenylbutynamine
Stimulant drug of the phenethylamine class
4-Methylphenylisobutylamine (4-MAB), also known as 4-methyl-α-ethylphenethylamine, is a stimulant drug of the phenethylamine, amphetamine, and phenylisobutylamine
4-Methylphenylisobutylamine
Stimulant and entactogen designer drug
as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy
Para-Methoxymethamphetamine
Chemical compound
3-Methoxytyramine (3-MT), also known as 3-O-methyldopamine or as 3-methoxy-4-hydroxyphenethylamine, is a human trace amine and the major metabolite of
3-Methoxytyramine
Medication used for high blood pressure and ADHD
posttraumatic stress disorder". Croatian Medical Journal. 49 (4): 459–475. doi:10.3325/cmj.2008.4.459. PMC 2525822. PMID 18716993. Kaminer D, Seedat S, Stein
Guanfacine
Stimulant drug used to treat hypotension
nitrile group to a primary amine giving 1,1-diphenyl-2-ethyl-3-aminopropanol (4). The tertiary hydroxyl group is dehydrated by treatment with anhydrous hydrogen
Etifelmine
Class of compounds based upon the amphetamine structure
stress disorder (PTSD). Substituted phenethylamines Substituted β-hydroxyamphetamines Substituted methylenedioxyphenethylamines Substituted cathinones
Substituted_amphetamine
Psychedelic drug found in toads, mushrooms and plants
chemical structure to other psychedelics such as 5-MeO-DMT and psilocin (4-HO-DMT). These compounds also occur in some of the same fungus, plant, and
Bufotenin
Decongestant medication
4 April 2015. "Preparation H – cocoa butter and phenylephrine hydrochloride suppository". DailyMed. U.S. National Institutes of Health. Retrieved 4 April
Phenylephrine
Chemical compound
phenmetrazine free base (3). The free base can be converted to the fumarate salt (4) by reaction with fumaric acid. Phenmetrazine was first patented in Germany
Phenmetrazine
Catecholamine hormone and neurotransmitter
interactions". Comprehensive Physiology. 4 (3): 1177–1200. doi:10.1002/cphy.c130051. ISBN 978-0-470-65071-4. PMC 4374437. PMID 24944034. Chistiakov DA
Norepinephrine
Psychoactive drug
prevalent metabolites in rats were 3-carboxymethyl-4-hydroxyamphetamine and 4-carboxymethyl-3-hydroxyamphetamine. 6-APB, also known as 6-(2-aminopropyl)benzofuran
6-APB
Chemical compound
reported in this paper are as follows: m.p. 55–57 °C; [α] = + 47.9° (c 2.4, in ethanol). Early, classical pharmacological studies of phenylethanolamine
Phenylethanolamine
Chemical compound
norepinephrine and about 11-fold more potently than serotonin. Similarly to cis-4-methylaminorex, the drug is notable in being one of the most selective dopamine
3-Chlorophenmetrazine
Pharmaceutical compound
also known as 4-bromomethamphetamine (4-BMA), is a monoaminergic drug of the amphetamine family related to para-chloroamphetamine (PCA; 4-chloroamphetamine)
Para-Bromomethamphetamine
Chemical compound
Substance Data Bank. Archived from the original on 16 September 2018. Retrieved 4 May 2014. The aim was to study the effect of trimethylamine (TMA) on the metabolism
N,N-Dimethylethylamine
Chemical compound
(PMEA), 4-ethoxyamphetamine (4-ETA), 4-methylthioamphetamine (4-MTA), 4-methylamphetamine (4-MA), 4-hydroxyamphetamine, para-chloroamphetamine
Para-Methoxyamphetamine
Monoamine that acts as a neurotransmitter or neuromodulator
are metabolized in the mammalian body via monoamine oxidase (MAO; EC 1.4.3.4) (Berry, 2004) (Fig. 2) ... It deaminates primary and secondary amines that
Monoamine_neurotransmitter
Synthetic decongestant
or as (1S,2S)-N-methyl-β-hydroxyamphetamine, is a substituted phenethylamine, amphetamine, and β-hydroxyamphetamine derivative. It is a diastereomer
Pseudoephedrine
Pharmaceutical compound
Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. p. 350. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 29 January 2025. v t e
Isocyclamine
Chemical compound
Methylbenzylpiperazine (1-methyl-4-benzylpiperazine, MBZP) is a stimulant drug which is a derivative of benzylpiperazine. MBZP has been sold as an ingredient
Methylbenzylpiperazine
Chemical compound
4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold
2C-B-BZP
Chemical compound
paediatric cough syrup: a case report". European Heart Journal: Case Reports. 4 (3): 1–4. doi:10.1093/ehjcr/ytaa095. PMC 7319816. PMID 32617471. Imai N, Yagi N
Methylephedrine
Simulant drug of the cathinone class
4-Chloromethcathinone (also known as 4-CMC and clephedrone) is a stimulant drug of the cathinone class that has been sold online as a designer drug. 4-CMC
4-Chloromethcathinone
Dopaminergic medication
Journal of Neural Transmission. 132 (6): 743–779. doi:10.1007/s00702-025-02893-4. PMC 12116664. PMID 40214767.{{cite journal}}: CS1 maint: overridden setting
Levodopa
Drug combination prescribed for weight loss; later withdrawn from market
study found a weight loss of 7.5 kg on average in 24 weeks, as compared to 4.4 kg under placebo. It sold modestly until the 1990s, when it was combined
Fenfluramine/phentermine
Investigational antipsychotic
Ergometrine Fenoldopam Fenoterol 4-Fluoroamphetamine Guanabenz Guanfacine Halostachine Higenamine Hordenine 4-Hydroxyamphetamine (norpholedrine) Idazoxan 5-Iodo-2-aminoindane
Ralmitaront
Stimulant drug of the amphetamine class
tests it substituted for dextroamphetamine more closely than either 3- or 4-methylamphetamine, although with only around 1/10 the potency of dextroamphetamine
Ortetamine
Designer drug combination mimicking MDMA
2-fluoromethamphetamine (2-FMA), and the serotonergic psychedelic 5-MeO-MiPT or 4-HO-MET, all at specific fixed doses. Contrary to its name, the Borax combo
Borax_combo
Chemical compound
piracetam--4-phenylpiracetam]". Biull Eksp Biol Med (in Russian). 95 (4): 50–53. doi:10.1007/BF00838859. PMID 6403074. "MRZ 9547". AdisInsight. 4 November
Phenylpiracetam
Pharmaceutical compound
Evaluation of Rigid Analogues of Methamphetamines". ScholarWorks@UNO. Retrieved 4 November 2024. Blough B (July 2008). "Dopamine-releasing agents" (PDF). In
Phenylpropylamine
Drug that releases serotonin and dopamine in the brain
35-fold selectivity for dopamine release over norepinephrine release and about 4-fold selectivity for serotonin release over dopamine release. Though selective
Serotonin–dopamine releasing agent
Serotonin–dopamine_releasing_agent
Drug class
Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine
Serotonin–norepinephrine releasing agent
Serotonin–norepinephrine_releasing_agent
Psychoactive stimulant and norepinephrine releasing agent
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
Phenylalaninol
Chemical compound
Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine
Heptaminol
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