Skip to content
PsychedeliaDokholyan Laboratory
Plate 473 of 545Verified

p-Methoxyamphetamine

PubChem records this structure as (+-)-p-Methoxyamphetamine.

Also known as(+-)-p-Methoxyamphetamine · 4-Methoxyamphetamine · paramethoxyamphetamine · 1-p-Methoxyphenyl-2-aminopropane · P-methoxyamfetamine · 4-methoxyamfetamine · (+-)-4-Methoxyamphetamine · 1-(4-methoxyphenyl)propan-2-amine

1-(4-methoxyphenyl)propan-2-amine

PubChem CID
31721
Measurements
5
InChIKey
NEGYEDYHPHMHGK-UHFFFAOYSA-N

I · Summary

What is known

Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.

What it is

  • 4-methoxyamphetamine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.

    Drug Enforcement Administration (DEA)

  • 4-methoxyamphetamine has been reported in Senegalia berlandieri with data available.

    LOTUS - the natural products occurrence database

  • para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation

    Medical Subject Headings (MeSH)

How it acts

  • 4-Methoxyamphetamine is a seratogenic drug of the amphetamine class. The drug acts as a potent and selective serotonin releasing agent. It binds to alpha receptors to mediate these effects.

    DrugBank

  • Phenylethylamines act on the peripheral and central nervous system by alpha- and beta-adrenergic stimulation. These compounds may also have varying degrees of serotonergic and dopaminergic activity, depending on structural similarity to mescaline. /Phenylethylamines/

    Hazardous Substances Data Bank (HSDB)Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 574

Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.

In the body

  • The qualitative and quantitative aspects of the urinary elimination of orally administered 4-methoxy(14C)amphetamine have been examined in the rat and guinea-pig and in three volunteer human subjects, to determine interspecies and interindividual variations in disposition of the drug. Both rat and guinea-pig excreted 70-80% of the administered dose (6 mg/kg) in the urine within 24 hr mainly as metabolites. In the guinea pig, the drug was metabolized by O-demethylation to give 4-hydroxyamphetamine, which was excreted free (4% dose) and conjugated (73%). No other metabolite was detected. The rat metabolizes the drug both by O-dealkylation and by side-chain oxidation, the products being 4-hydro…

    Absorption, Distribution and Excretion

    Hazardous Substances Data Bank (HSDB)PMID 582863Kitchen I et al; Xenobiotica 9 (7): 397-404 (1979)

  • Amphetamine (AM) and five amphetamine derivatives, N-ethylamphetamine (NEA), N-butylamphetamine (NBA), 4-methoxyamphetamine (M-AM), 4-methoxy-N-ethylamphetamine (M-NEA) and 4-methoxy-N-butylamphetamine (M-NBA) were incubated with microsomal preparations from cells expressing human CYP2D6 to determine whether the enzyme was capable of catalyzing the direct ring oxidation of all substrates; the N-dealkylation of NEA, NBA, M-NEA and M-NBA; and the O-demethylation of M-AM, M-NEA and M-NBA. None of the six compounds examined was N-dealkylated to any extent. The only metabolites produced from AM, NEA and NBA were the corresponding ring 4-hydroxylated compounds, and the rates of formation were lo…

    Metabolism/Metabolites

    Hazardous Substances Data Bank (HSDB)PMID 10456690Bach MV et al; Xenobiotica 29 (7): 719-32 (1999)

  • Metabolites of p-methoxyamphetamine in the urine of dogs and monkeys were separated by gas-liquid chromatography as their trifluoroacetyl derivatives, and identified by comparison of the chromatographic and mass spectrometric behavior of these derivatives with those of authentic synthetic compounds. The three new metabolites identified in both dogs and monkeys were 3-O-methyl-alpha-methyldopamine, 4-hydroxy-3-methoxybenzyl methyl ketone, and 4-hydroxybenzyl methyl ketone. A fourth new metabolite was tentatively identified in the absence of the appropriate reference standard.

    Metabolism/Metabolites

    Hazardous Substances Data Bank (HSDB)PMID 6113935Hubbard JW et al; Drug Metab Dispos 9 (3): 250-4 (1981)

  • The qualitative and quantitative aspects of the urinary elimination of orally administered 4-methoxy[14C]amphetamine have been examined in the rat and guinea-pig and in three volunteer human subjects, to determine interspecies and interindividual variations in disposition of the drug. ... In the guinea-pig, the drug was metabolized by O-demethylation to give 4-hydroxyamphetamine, which was excreted free (4% dose) and conjugated (73%). No other metabolite was detected. The rat metabolizes the drug both by O-dealkylation and by side-chain oxidation, the products being 4-hydroxyamphetamine (5% of dose free and 60% conjugated) and 1-(4'-methoxyphenyl)propan-2-one oxime (5% dose, free and conjug…

    Metabolism/Metabolites

    Hazardous Substances Data Bank (HSDB)PMID 582863Kitchen I et al; Xenobiotica 9 (7): 397-404 (1979)

  • ... Three recent fatalities that occurred in the midwestern United States in which each of the decedents believed that they were ingesting methylenedioxymethamphetamine (MDMA) /were reported/. ... The deceased, two males ages 19 and 24 and a female age 18, had postmortem blood paramethoxyamphetamine (PMA) concentrations of 1.07, 0.60, and 1.90 mg/L, respectively. PMA is not a contaminant of MDMA, and no MDMA was found in any of these cases. The primary metabolite of PMA is produced by O-demethylation to 4-hydroxyamphetamine, a reaction catalyzed by cytochrome P450 2D6. This enzyme is noted to be genetically polymorphic. Those with the "slow metabolizer" phenotype may be likely to have highe…

    Metabolism/Metabolites

    Hazardous Substances Data Bank (HSDB)PMID 11599617Kraner JC et al; J Anal Toxicol 25 (7): 645-8 (2001)

History, discovery and cultural use

— Not in this archive. PubChem, ChEMBL and the Human Protein Atlas publish pharmacology, regulation and toxicology, and none of them publishes a heading for when p-Methoxyamphetamine was first made, by whom, or how it has been used. That is a gap in the databases this site reads and not a gap in the literature — the history of these compounds is written, at length and under peer review, in the works below. This site does not summarize them; it says where they are. Where a published passage above happens to touch origin or traditional use, it appears inside the entry that carries it.

Histories of this field

Scholarship on psychedelics generally, not on p-Methoxyamphetamine specifically. Whether any of these treats this compound is a question for the book, not for this page.

  • Mescaline: A Global History of the First Psychedelic

    Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.

    Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.

  • Expanding Mindscapes: A Global History of Psychedelicsopen access

    Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.

    Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.

  • Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers

    Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.

    Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.

  • Psychonauts: Drugs and the Making of the Modern Mind

    The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.

    Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.

  • Ancient Psychoactive Substances

    Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.

    Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.

  • History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders

    A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.

    Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.

    Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.

  • Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions

    Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.

    Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.

Institutional archives

  • Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
  • Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.

The rest of this dossier

  • Affinity — 5 measurements in this archive, equilibrium constants kept apart from functional readouts.
  • Toxicology — 5 published passages, plus any assay in this archive bearing on toxicity.
  • Legal — DEA Schedule I, with the passage it was read from.
  • Systems — where this compound’s targets are transcribed, by brain region and tissue.

Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about p-Methoxyamphetamine is the history note, which says so on its face and carries a reference for every claim in it.

II · Identity

Structure and descriptors

Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.

2D structural depiction of p-Methoxyamphetamine
Depiction served by PubChem for CID 31721. Not redrawn here, so the picture and the identity come from the same record.
Formula
C10H15NOR
Molecular weight
165.24g/molR
Exact mass
165.1154DaR
cLogP
1.58R
TPSA
35.3ŲR
H-bond donors
1R
H-bond acceptors
2R
Rotatable bonds
3R
Aromatic rings
1R
Heavy atoms
12R
Fraction sp³
0.400R
Formal charge
0R

Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.

Bemis–Murcko scaffold

c1ccccc1

Shared with 2-Bromomescaline, 2-TOET, 2-TOM, 2,3,4,5-Tetramethoxyamphetamine, 2,4-dimethoxyamphetamine, 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine and 129 more. All families

III · Behavior

Behavioral summary

Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.

Classification

Duration of acute subjective effects

—

No controlled human trial reporting a duration for this compound is cited here. The archive holds no other record of one either. A duration is not inferred from a chemical relative.

Plasma elimination half-life

How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.

No half-life is published for this compound in the sources this site reads.

Primary pharmacological drivers

ChEMBL holds no curated mechanism-of-action record for this compound. The measured affinities below are the evidence this archive has for what it binds.

Mechanism, as published

Quoted verbatim from the database named after each passage, never summarized.

  • It is well established that the commonly used recreational drugs 3,4-methylenedioxymethamphetamine (MDMA, 'ecstasy') and para-methoxyamphetamine (PMA) facilitate the release and prevent the reuptake of 5-hydroxytryptamine (5-HT, serotonin). Although these drugs have similar potencies for their abilities to increase the release and inhibit…
    Hazardous Substances Data Bank (HSDB)PMID 17714093Hewton R et al; Clin Exp Pharmacol Physiol 34 (10): 1051-7 (2007)
  • This study was prompted by recent deaths that have occurred after recreational administration of the substituted amphetamine para-methoxyamphetamine (PMA). Because relatively little is known regarding its mechanism(s) of action, its effects on physiological, behavioral and neurochemical parameters were compared with the well known effects…
    Hazardous Substances Data Bank (HSDB)PMID 11041537Daws LC et al; Prog Neuropsychopharmacol Biol Psychiatry 24 (6): 955-77 (2000)
  • 4-Methoxyamphetamine is a seratogenic drug of the amphetamine class. The drug acts as a potent and selective serotonin releasing agent. It binds to alpha receptors to mediate these effects.
    DrugBank
  • Phenylethylamines act on the peripheral and central nervous system by alpha- and beta-adrenergic stimulation. These compounds may also have varying degrees of serotonergic and dopaminergic activity, depending on structural similarity to mescaline. /Phenylethylamines/
    Hazardous Substances Data Bank (HSDB)Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 574

IV · Clinical

Clinical description

Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.

Filed under Hallucinogens

  • 6C49Disorders due to use of hallucinogens

Diagnostic and Statistical Manual of Mental Disorders, Fifth Edition, Text Revision (DSM-5-TR): Hallucinogen-Related Disorders. Category names only — the manual is in copyright and no diagnostic criterion is reproduced here.

How much has been written about each domain

The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.

Affect0Mood0Perception1Cognition3Thought process0Thought content0Psychomotor activity2Insight and judgment0
This measures the literature, not the compound. Each spoke counts how many of the 9 records this archive holds for this compound say something under that domain — 3 at the widest ring. A long spoke means the subject has been written about, not that the effect is strong, and a spoke at the center means nothing here discusses it rather than that nothing happens. The terms behind each domain are listed in the method.
Perception 1
matched on “altered perception” · in Toxicology: Hazardous Substances Data Bank (HSDB)
Cognition 3
matched on “concentrat” · in PMID 17714093; PMID 12820749; PMID 11599617
Psychomotor activity 2
matched on “agitat” · in Toxicology: Hazardous Substances Data Bank (HSDB); PMID 11599617

V · Systems

Systems physiology

Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.

Brain

cerebral cortex — 20.0 nTPM, from MAOAcerebellum — 4.0 nTPM, from MAOAhippocampal formation — 14.8 nTPM, from MAOAamygdala — 21.5 nTPM, from MAOAhypothalamus — 21.2 nTPM, from MAOAthalamus — no resolved target expressed herebasal ganglia — 22.0 nTPM, from MAOAmedulla oblongata — no resolved target expressed here

basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.

Measured but not drawn — this anatomogram has no outline for them: midbrain 34.6, retina 24.3, spinal cord 7.9, pituitary gland 3.4.

Body

heart — 44.8 nTPM, from MAOAsmooth muscle — 21.4 nTPM, from MAOAlung — 56.9 nTPM, from MAOAliver — 103.3 nTPM, from MAOAkidney — 69.7 nTPM, from MAOAstomach — 50.0 nTPM, from MAOAduodenum — 143.7 nTPM, from MAOAsmall intestine — 206.3 nTPM, from MAOAcolon — 104.7 nTPM, from MAOAadrenal gland — 24.9 nTPM, from MAOAthyroid gland — 105.7 nTPM, from MAOApancreas — 35.0 nTPM, from MAOAurinary bladder — 61.9 nTPM, from MAOAskeletal muscle — 29.0 nTPM, from MAOAspleen — 5.6 nTPM, from MAOAsalivary gland — 66.9 nTPM, from MAOA
0206 nTPM

Square-root ramp · shared scale across both plates

Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.

Brain regions

Regions where this compound's measured targets are transcribed. Linked from the plate above.

  1. midbrain

    34.6 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX34.6

  2. retina

    24.3 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX24.3

  3. basal ganglia

    22.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX22.0

  4. amygdala

    21.5 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX21.5

  5. hypothalamus

    21.2 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX21.2

  6. cerebral cortex

    20.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX20.0

  7. hippocampal formation

    14.8 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX14.8

  8. spinal cord

    7.9 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX7.9

  9. cerebellum

    4.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX4.0

  10. pituitary gland

    3.4 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX3.4

Peripheral & autonomic

Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.

  1. small intestine

    206.3 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX206.3

  2. duodenum

    143.7 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX143.7

  3. thyroid gland

    105.7 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX105.7

  4. colon

    104.7 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX104.7

  5. liver

    103.3 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX103.3

  6. kidney

    69.7 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX69.7

  7. salivary gland

    66.9 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX66.9

  8. urinary bladder

    61.9 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX61.9

  9. lung

    56.9 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX56.9

  10. stomach 1

    50.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX50.0

  11. heart muscle

    44.8 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX44.8

  12. pancreas

    35.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX35.0

  13. skeletal muscle

    29.0 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX29.0

  14. adrenal gland

    24.9 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX24.9

  15. smooth muscle

    21.4 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX21.4

  16. spleen

    5.6 nTPM
    • Amine oxidase [flavin-containing] AMAOA6.6 pX5.6

Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.

3 of this compound’s targets could not be resolved to a gene and are absent from both columns: 5-HT1, 5-HT2, Serotonin (5-HT) receptor.

Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.

VI · Profile

Affinity rosette

The strongest measurement at each of 4 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.

Serotonin (5-HT) receptor — Kd 5.15 pX5-HT2 — Ki 4.47 pX5-HT1 — Ki 4.10 pXAmine oxidase [flavin-containing] A — Ki 6.60 pXSerotonin (5-HT)…5-HT25-HT1Amine oxidase [f…579
Fig. Radius is pX = −log₁₀(value in M), that is 9 − log₁₀(value in nM), computed from the normalized measurement. Hatched wedges are equilibrium binding constants (Ki, Kd); dashed outlines are functional readouts (IC₅₀, EC₅₀, AC₅₀, potency), which answer a different question and are not pooled with them. Rings mark whole pX units from 5 to 10, labeled every second ring in the gutter at the top. Where a target carries several measurements, the strongest is drawn.

VII · Toxicology

Toxicological profile

What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.

Measured in this archive

Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.

No hERG, cytochrome, cytotoxicity or transport measurement exists for p-Methoxyamphetamine in this archive.

As published

Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.

Human Toxicity Excerpts

  • /SIGNS AND SYMPTOMS/ Central nervous system effects may be secondary to both sympathetic stimulation and altered perception. Therapeutic or recreational doses may induce feelings of warmth and are purported to promote communication and empathy. Higher doses may induce hallucinations, agitation, delirium, hyperreflexia, or rigidity. Seizures may occur and can reflect either direct CNS stimulation or hypertension induc…

    Hazardous Substances Data Bank (HSDB)Haddad, L.M. (Ed). Clinical Management of Poisoning and Drug Overdose 3rd Edition. Saunders, Philadelphia, PA. 1998., p. 574

  • /CASE REPORTS/ ... A 16-year-old male was admitted to a local hospital in a coma with seizures and hyperthermia after he had been found undressed and barefooted in a local forest (temperature 2 degrees C). He was intubated and given supportive care. Blood chemistry revealed hypoglycemia, hypocalcemia and hyperkalemia. Shortly after transfer to the central hospital he developed bradycardia with continuous seizures and…

    Hazardous Substances Data Bank (HSDB)PMID 14616331Refstad S; Acta Anaesthesiol Scand 47 (10): 1298-9 (2003)

  • /CASE REPORTS/ ... Three fatal cases involving p-methoxyamphetamine (PMA) and p-methoxymethamphetamine (PMMA) in Denmark in year 2000 are investigated including history, pathological, and toxicological findings. The methods used for extraction, identification, and quantitation of PMA and PMMA are described. In two of the cases, lethal postmortem blood concentrations of PMA and PMMA were determined at 3.4 and 3.3 mg/k…

    Hazardous Substances Data Bank (HSDB)PMID 12820749Johansen SS et al; J Anal Toxicol 27 (4): 253-6 (2003)

  • /CASE REPORTS/ ... Three recent fatalities that occurred in the midwestern United States in which each of the decedents believed that they were ingesting methylenedioxymethamphetamine (MDMA) /were reported/. Symptoms observed included agitation and bruxism, progressing to severe hyperthermia, convulsions, and hemorrhage. Blood was screened for drugs of abuse by enzyme immunoassay with the presence of amphetamines in…

    Hazardous Substances Data Bank (HSDB)PMID 11599617Kraner JC et al; J Anal Toxicol 25 (7): 645-8 (2001)

  • For more Human Toxicity Excerpts (Complete) data for 4-METHOXYAMPHETAMINE (8 total), please visit the HSDB record page.

    Hazardous Substances Data Bank (HSDB)

Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.

VIII · Evidence

Every measurement

One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.

Equilibrium binding constants 5

Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.

TargetClassTypeValue (nM)pXOrganismAssay
Amine oxidase [flavin-containing] AEnzymesKi2506.60Rattus norvegicusCHEMBL1022171
Serotonin (5-HT) receptorSerotonin receptorsKd7,0795.15Rattus norvegicusCHEMBL619177
Serotonin (5-HT) receptorSerotonin receptorsKd7,0795.15Rattus norvegicusCHEMBL619176
5-HT2Serotonin receptorsKi33,6004.47Rattus norvegicusCHEMBL617444
5-HT1Serotonin receptorsKi79,4004.10Rattus norvegicusCHEMBL615400
P
PubChem
C
ChEMBL
R
Computed here with RDKit
D
Derived here from the stored measurement

IX · Trials

Registered clinical trials

Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.

— No registered study names p-Methoxyamphetamine as an intervention. That is an absence of registered research, not evidence about the compound. Most of this archive has never been the subject of a registered trial.

Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.

Searched as p-Methoxyamphetamine · (+-)-p-Methoxyamphetamine · 4-Methoxyamphetamine. Run this search at the registry.

A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether p-Methoxyamphetamine worked.

XI · Literature

Sources behind this dossier

The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.

Every paper below is one some value on this page came from — a binding constant, a passage of pharmacology or toxicology, or a measured duration. Each entry says what this archive took from it. Nothing else is claimed about any of them: the title is the study’s own account of itself, and a summary written here would be an assertion with no source behind it.

  1. 01

    Potentiation of 3,4-methylenedioxymethamphetamine-induced 5-HT release in the rat substantia nigra by clorgyline, a monoamine oxidase A inhibitor

    Hewton R, Salem A, Irvine RJ · Clinical and experimental pharmacology & physiology 2007

    • · Mechanism of Action

    PMID 17714093

  2. 02

    Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects

    Refstad S · Acta anaesthesiologica Scandinavica 2003

    • · Human Toxicity Excerpts

    PMID 14616331

  3. 03

    Three fatal cases of PMA and PMMA poisoning in Denmark

    Johansen SS, Hansen AC, Müller IB et al. · Journal of analytical toxicology 2003

    • · Human Toxicity Excerpts

    PMID 12820749

  4. 04

    Fatalities caused by the MDMA-related drug paramethoxyamphetamine (PMA)

    Kraner JC, McCoy DJ, Evans MA et al. · Journal of analytical toxicology 2001

    • · Human Toxicity Excerpts

    PMID 11599617

  5. 05

    Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat

    Daws LC, Irvine RJ, Callaghan PD et al. · Progress in neuro-psychopharmacology & biological psychiatry 2000

    • · Mechanism of Action

    PMID 11041537