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Group of stereoisomers
4-Methylaminorex (4-MAR, 4-MAX) is a stimulant drug of the 2-amino-5-aryloxazoline group that was first synthesized in 1960 by McNeil Laboratories. It
4-Methylaminorex
Chemical compound
4'-Fluoro-4-methylaminorex (4F-MAR, 4-FPO) is a recreational designer drug from the substituted aminorex family, with stimulant effects. It was first
4'-Fluoro-4-methylaminorex
Chemical compound
3',4'-Methylenedioxy-4-methylaminorex (MDMAR) is a recreational designer drug from the substituted aminorex family, with monoamine-releasing effects. It
MDMAR
Chemical compound
4'-Chloro-4-methylaminorex (4C-MAR, 4'-Cl-4-MAR) is a recreational designer drug from the substituted aminorex family, with stimulant effects. It has
4C-MAR
Chemical compound
2'-Fluoro-4-methylaminorex (2F-MAR, 2'-F-4-MAR) is a recreational designer drug from the substituted aminorex family, with stimulant effects, first reported
2F-MAR
failure, which resulted in a number of deaths. A designer drug analogue 4-methylaminorex appeared on the illicit market in the late 1980s but did not attract
List_of_aminorex_analogues
Chemical compound
4'-Bromo-4-methylaminorex (4B-MAR, 4'-Br-4-MAR) is a designer drug from the substituted aminorex family, first definitively identified in Austria in January
4B-MAR
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
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
Chemical compound
4-HO-MET, also known as 4-hydroxy-N-methyl-N-ethyltryptamine, as well as metocin or methylcybin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine
4-HO-MET
Psychoactive drug, often called ecstasy
humans include 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-dihydroxyamphetamine
MDMA
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
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
Chemical compound
2'-fluoro-4-methylaminorex (2F-MAR), 2C-B-aminorex, 3',4'-methylenedioxy-4-methylaminorex (MDMAR), 4'-bromo-4-methylaminorex (4B-MAR), 4'-chloro-4-methylaminorex
Aminorex
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
Pharmaceutical compound
as pemoline and 4'-Fluoro-4-methylaminorex. 2F-MAR 3-Fluoroamphetamine 3-Fluoromethcathinone 3-Fluorophenmetrazine 4-Methylaminorex Fluminorex Yurchenko
3F-Thozalinone
Psychoactive research chemical
(3-FA) 3,4-Difluoroamphetamine 4-Fluoromethamphetamine (4-FMA) 4-Fluoromethcathinone (4-FMC) 4'-Fluoro-4-methylaminorex para-Bromoamphetamine (PBA)
4-Fluoroamphetamine
Pharmaceutical compound
4-Methylephedrine (4-ME), also known as dihydromephedrone (DHMMC) or as β-hydroxy-4-methylmethamphetamine, is a putative stimulant drug of the phenethylamine
4-Methylephedrine
Central nervous system stimulant
metabolites are amphetamine and 4-hydroxymethamphetamine; other minor metabolites include: 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone,
Methamphetamine
Drug mixture used mainly to treat ADHD and narcolepsy
a variety of excreted metabolic products, including 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, N-hydroxyamphetamine, benzoic
Adderall
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
Psychedelic drug
potent psychological effects. LSD taken orally has an onset of action of 0.4 to 1.0 hours and a duration of 7 to 12 hours. In recreational settings it
LSD
Medication mainly used for depression and smoking cessation
on 4 June 2020. Retrieved 6 May 2020. "Wellbutrin XL – bupropion hydrochloride tablet, extended release". DailyMed. National Institutes of Health. 4 March
Bupropion
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
Central nervous system stimulant prodrug
a variety of excreted metabolic products, including 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, N-hydroxyamphetamine, benzoic
Lisdexamfetamine
Medication to prevent nausea and vomiting
significantly lower at 3.9 (3.3 to 4.8). When all 25 reports were combined, the apparent NNT improved to 4.9 (4.4 to 5.6). Inclusion of duplicate reports
Ondansetron
Beta blocker drug
unopposed α-stimulation with selective beta blockers has been reported to be 0.4%, whereas no cases of unopposed α-stimulation have been reported with dual
Propranolol
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
Synthetic decongestant
found no significant difference in weight lost compared to placebo (-4.6 kg vs. -4.5 kg). This was in contrast to phenylpropanolamine, which has been found
Pseudoephedrine
Chemical compound
psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex, and pemoline. It was first detected in the Netherlands in December
4,4'-Dimethylaminorex
Antidepressant medication
CYP1A2 inducer, increased trazodone peak levels by 1.4-fold, trazodone area-under-the-curve levels by 2.4-fold, and decreased trazodone clearance by 50%. This
Trazodone
CNS stimulant and isomer of amphetamine
a variety of excreted metabolic products, including 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, N-hydroxyamphetamine, benzoic
Dextroamphetamine
Medication used to treat anxiety disorders
contribute to its clinical efficacy. It has a delayed onset of action of 2–4 weeks. Buspirone also has weak antagonistic effects at dopamine D2, D3, and
Buspirone
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
Psychoactive drug and research chemical
4-Bromomethcathinone (4-BMC, 4-BMAP), also known as brephedrone, is a psychoactive drug and research chemical of the phenethylamine, amphetamine, and cathinone
4-Bromomethcathinone
Atypical antipsychotic medication
of insomnia of 0.05 (95% CITooltip confidence interval –1.21 to 1.11) at 4 weeks of treatment, with the certainty of evidence rated as very low. Doses
Quetiapine
Pharmaceutical compound
Analogues of 4-PrO-DiPT include 4-HO-DiPT (iprocin), 4-AcO-DiPT (ipracetin), luvesilocin (4-GO-DiPT), 4-PrO-DMT, 4-PrO-MET, and 4-GO-DMT, among others. 4-PrO-DiPT
4-PrO-DiPT
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
Chemical compound
O-glucuronidation, O-methylation, N-demethylation, and sulfation. Only 3–4% of the apomorphine is excreted unchanged and into the urine. The half-life
Apomorphine
Family of phenethylamine psychedelics
benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and
2C_(psychedelics)
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
Naturally occurring psychedelic compound
spiritual experiences, with an onset of 30 to 60 minutes, a time to peak of 2 to 4 hours, and a duration that increases with dose and ranges from 6 to 14 hours
Mescaline
Chemical compound
indicated that the major metabolites of 5-MAPB are 5-APB and 3-carboxymethyl-4-hydroxymethamphetamine. The chemical synthesis of 5-MAPB has been described
5-MAPB
Substance that mimics effects of catecholamines
methcathinone methylenedioxypyrovalerone (MDPV) methylphenidate (Ritalin) 4-methylaminorex oxymetazoline (Afrin, Vicks Sinex) pemoline (Cylert) phenmetrazine
Sympathomimetic_drug
Antihistamine drug
"Hydroxyzine". United States National Library of Medicine (NLM). Retrieved 4 March 2020. "Hydroxyzine". Go.drugbank.com. Retrieved 9 June 2026. "Hydroxyzine"
Hydroxyzine
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
Antidepressant medication
Organization project". Expert Review of Anticancer Therapy. 2 (4): 365–376. doi:10.1586/14737140.2.4.365. PMID 12647979. S2CID 72195061. Clark MS, Smith PO,
Mirtazapine
Mushrooms containing psychoactive indole alkaloids
(14), Panaeolus (13), Copelandia (12), Pluteus (6) Inocybe (6), Pholiotina (4) and Galerina (1). Guzmán increased his estimate of the number of psilocybin-containing
Psilocybin_mushroom
Class of compounds based upon the amphetamine structure
to treat attention deficit hyperactivity disorder (ADHD) [79]. ... [Figure 4](b) Examples of synthetic, pharmaceutically important substituted amphetamines
Substituted_amphetamine
Psychedelic drug
4-HO-DET, also known as 4-hydroxy-N,N-diethyltryptamine as well as ethocin or CZ-74, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families
4-HO-DET
Central nervous system stimulant
clinical needs and research opportunities". Pediatrics. 108 (4): 983–989. doi:10.1542/peds.108.4.983. PMID 11581454. S2CID 33417584. Hermens DF, Rowe DL,
Methylphenidate
Stimulant and anorectic drug of the amphetamine class
4-Methylamphetamine (4-MA) or para-methylamphetamine, also known by the former proposed brand name Aptrol, is a stimulant and anorectic drug of the amphetamine
4-Methylamphetamine
Serotonergic compound
4-HO-TMT, or 4-OH-TMT, also known as 4-hydroxy-N,N,N-trimethyltryptammonium or as dephosphorylated aeruginascin, is a substituted tryptamine derivative
4-HO-TMT
Chemical compound
4-HO-DPT, also known as 4-hydroxy-N,N-dipropyltryptamine or as deprocin, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related
4-HO-DPT
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
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
Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex •
List_of_dopaminergic_drugs
Chemical compound
adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research. 4 (2): 147–150. doi:10.1080/10298420290015827. eISSN 1476-3524. ISSN 1029-8428
Adrenochrome
CHCl3, historical anaesthetic and common solvent
Simpson considerable notoriety. Whatever the source of his inspiration, on 4 November 1847, Simpson argued that he had discovered the anaesthetic qualities
Chloroform
Dissociative hallucinogenic drug, mostly used recreationally
treatment of phencyclidine psychosis". Journal of Clinical Pharmacology. 24 (4): 202–4. doi:10.1002/j.1552-4604.1984.tb01831.x. PMID 6725621. S2CID 42278510
Phencyclidine
Synthetic opioid pain medication
more of acute withdrawal symptoms can occur as opposed to typically 3 or 4 days for other codeine analogs. The clinical presentation in overdose cases
Tramadol
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
Pharmaceutical compound
4-Methyl-DMT, or 4-Me-DMT, also known as 4-methyl-N,N-dimethyltryptamine or as 4,N,N-trimethyltryptamine (4,N,N-TMT or 4-TMT), is a serotonin receptor
4-Methyl-DMT
Muscle relaxant medication
fibromyalgia symptoms, with a reported number needed to treat of 4.8 (meaning that 1 person out of every 4.8 benefits from treatment) for pain reduction, but no
Cyclobenzaprine
Serotonin modulator antidepressant
other serotonin receptors. Whereas vortioxetine has IC50 or EC50 values of 5.4 nM for the SERT and 12 nM for the 5-HT3 receptor, its values are 120 to 450 nM
Vortioxetine
Pharmaceutical compound
4-AcO-MPT, also known as 4-acetoxy-N-methyl-N-propyltryptamine, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to 4-AcO-DMT
4-AcO-MPT
South American psychoactive decoction
and therapeutic aspects". Psychiatry and Clinical Neurosciences Reports. 2 (4) e146. doi:10.1002/pcn5.146. PMC 11114307. PMID 38868739. PubChem. "Dimethyltryptamine"
Ayahuasca
SSRI antidepressant
delivery (by 55%), lower birth weight (by 75 g), and lower Apgar scores (by <0.4 points). There is 30–36% increase in congenital heart defects among children
Fluoxetine
Stimulant designer drug
(3-FEA) 4-Bromomethamphetamine (4-BMA) 4-Chloromethamphetamine (4-CMA) 4-Fluoroamphetamine (4-FA) 4-Fluoromethcathinone (4-FMC) 4-Methylmethamphetamine (4-MMA)
4-Fluoromethamphetamine
Chemical compound
4-yl)indole-5-yl)ethanesulfonamide::N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide::N-methyl-2-[3-(1-methylpiperidin-4
Naratriptan
Chemical compound
in 1901. Hopkins recovered tryptophan from hydrolysed casein, recovering 4–8 g of tryptophan from 600 g of crude casein. Tryptophan is not synthesized
Tryptophan
Pharmaceutical compound
Modafinil Oxazolines 4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines 1-(4-Methylphenyl)-2-aminobutane
Octodrine
Pharmaceutical compound
4-HO-NBnT include norpsilocin (4-HO-NMT), 4-HO-NET, 4-HO-NPT, 4-HO-NiPT, 4-HO-NALT, 4-HO-NBT (4-HO-NnBT), 4-HO-NtBT, and 4-HO-NcHT, among others. 4-HO-NBnT
4-HO-NBnT
Antihistamine medication
humans". Experimental and Clinical Psychopharmacology. 4 (4): 421–430. doi:10.1037/1064-1297.4.4.421. "TikTok Videos Encourage Viewers to Overdose on Benadryl"
Diphenhydramine
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
nitrogen. 4'-Bromo-4-methylaminorex, 4'-B-4-MAR, 4B-MAR 4'-Chloro-4-methylaminorex, 4'-C-4-MAR, 4C-MAR 4'-Fluoro-4-methylaminorex, 4'-F-4-MAR, 4F-MAR
List_of_designer_drugs
Trace amine
DBH, and CYP2D6. Human monoamine oxidase enzymes metabolize tyramine into 4-hydroxyphenylacetaldehyde. If monoamine metabolism is compromised by the use
Tyramine
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
Atypical antipsychotic medication
ema.europa.eu. European Medicines Agency. 4 June 2004. Archived from the original on 15 April 2024. Retrieved 4 July 2024. "Abilify Tablets, Orodispersible
Aripiprazole
Type of drug
dopamine versus norepinephrine release. A few NDRAs, including cis-4-methylaminorex (cis-4-MAR), 3-chlorophenmetrazine (3-CPM; PAL-594), and naphthylmetrazine
Dopamine_releasing_agent
Serotonin receptor agonist
4-HO-MBT 4-HO-McPeT 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiBT 4-HO-MiPT (miprocin) 4-HO-MPMI (lucigenol) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-MtBT 4-HO-NALT 4-HO-NBnT
4-Hydroxytryptamine
Synthetic hallucinogen
(between gum and cheek). When it is insufflated (snorted), effects usually last 4–6 hours. 25I-NBOMe has similar effects to LSD, though users report more negative
25I-NBOMe
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
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
Serotonin receptor protein distributed in the cerebrum and raphe nucleus
Findings in Experimental and Clinical Pharmacology. 29 (4): 269–272. doi:10.1358/mf.2007.29.4.1075362. PMID 17609739. Monti JM, Jantos H (September 1992)
5-HT1A_receptor
Chemical compound
4-HO-MPMI, also known as 4-hydroxy-N-methyl-(α,N-trimethylene)tryptamine or as lucigenol, is a psychedelic drug of the pyrrolidinylmethylindole and cyclized
4-HO-MPMI
Antipsychotic medication
or intramuscular). The injectable versions are long-acting and last for 2–4 weeks. Common side effects include weight gain, drowsiness, fatigue, insomnia
Risperidone
Common name for flowering plants in the family Convolvulaceae
are structurally related to LSD and can produce psychedelic effects lasting 4 to 10 hours when ingested in sufficient quantities. Ipomoea nil, a species
Morning_glory
Chemical compound
2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is little-used recreationally, but
2,5-Dimethoxy-4-iodoamphetamine
2,5-Dimethoxy-4-iodoamphetamine
Medication used for migraines & cluster headaches
reported by 4% in the placebo group and 5–6% in the sumatriptan groups, pain and other pressure sensations (including chest pain) reported by 4% in the placebo
Sumatriptan
Recreational drug
Vesnarinone – Cardiotonic Designer drugs 3-Methylbenzylpiperazine 4-Methyl-1-benzylpiperazine (MBZP) 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) 1,4-Dibenzylpiperazine
Benzylpiperazine
Species of flowering plant
PMC 9414117. PMID 36008824. Panten J, Surburg H (2015). "Flavors and Fragrances, 4. Natural Raw Materials". Ullmann's Encyclopedia of Industrial Chemistry. pp
Valerian_(herb)
Sedating antidepressant
(standardized mean difference (SMD)) against placebo for treatment of insomnia at 4 weeks of 0.30 (95% CITooltip confidence interval –0.05 to 0.64). The certainty
Doxepin
Pharmaceutical compound
to psilocin (4-HO-DMT). It is an analogue of 4-HO-MiPT (miprocin) and 4-HO-DiPT (iprocin) and a derivative of norpsilocin (4-HO-NMT) and 4-HO-NET. The
4-HO-NiPT
Pharmacodynamics and pharmacokinetics of ethanol
following first-order kinetics, with an elimination half-life of about 4 or 4.5 hours (a clearance rate of approximately 6 L/hour/70 kg). This is thought
Pharmacology_of_ethanol
Psychedelic tryptamine
diisopropyltryptamine (DiPT) and is an analogue of other psychedelic tryptamines like 4-HO-DiPT, 5-MeO-DMT, and 5-MeO-MiPT. 5-MeO-DiPT was first described in the
5-MeO-DiPT
Serotonin-norepinephrine-dopamine reuptake inhibitor
Older" (Press release). Otsuka. 24 July 2026. Archived from the original on 4 August 2026. Retrieved 25 July 2026. Bymaster FP, Golembiowska K, Kowalska
Centanafadine
Chemical compound
Publications. p. 1751. ISBN 978-0-9626523-9-4. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF)
Α-Pyrrolidinopentiophenone
Chemical compound
non-specific edema (2%). Arrhythmias were encountered in 4.8%, palpitations in 4.3%, and angina pectoris in 1.4%. In a combination study with 2,000 patients also
Cabergoline
Tricyclic antidepressant
an octanol-water partition coefficient (pH 7.4) of 3.0, while the log P of the free base was reported as 4.92. Solubility of the free base amitriptyline
Amitriptyline
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