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COO/COA

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M3404

(±)-p-Methoxyamphetamine hydrochloride

Name: (±)-<I>p</I>-Methoxyamphetamine hydrochloride
Brand: SIGMA

Synonym(s):

PMA hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₅NO · HCl

CAS Number:

52740-56-4

Molecular Weight:

201.69

MDL number:

MFCD00051431

UNSPSC Code:

12352200

PubChem Substance ID:

24896840

This product is discontinued. Contact Technical Servicefor assistance.

drug control

USDEA Schedule I; Home Office Schedule 1; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
veterinary

SMILES string

Cl.COc1ccc(CC(C)N)cc1

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Biochem/physiol Actions

CNS stimulant and hallucinogen; more potent transport inhibitor and releaser of serotonin than of dopamine.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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4-Ethoxyamphetamine: effects on intracranial self-stimulation and in vitro uptake and release of 3H-dopamine and 3H-serotonin in the brains of rats.

K M Hegadoren et al.

Journal of psychiatry & neuroscience : JPN, 19(1), 57-62 (1994-01-01)

Experiments were conducted to compare the effects of 4-ethoxyamphetamine, a novel "designer" amphetamine, with (+)-amphetamine and an earlier "designer" amphetamine, 4-methoxyamphetamine, on rats. (+)-Amphetamine significantly decreased frequency threshold measures in an intracranial self-stimulation (ICSS) procedure using medial forebrain bundle electrodes

Interactions of amphetamine analogs with human liver CYP2D6.

D Wu et al.

Biochemical pharmacology, 53(11), 1605-1612 (1997-06-01)

The interaction of fifteen amphetamine analogs with the genetically polymorphic enzyme CYP2D6 was examined. All fourteen phenylisopropylamines tested were competitive inhibitors of CYP2D6 in human liver microsomes. The presence of a methylenedioxy group in the 3,4-positions of both amphetamine (Ki

Repeated administration of the substituted amphetamine p-methoxyamphetamine produces reductions in cortical 5-HT transporter binding but not 5-HT content, unlike 3,4-methylenedioxyamethamphetamine.

Paul D Callaghan et al.

European journal of pharmacology, 546(1-3), 74-81 (2006-08-24)

Worldwide growth in p-methoxyamphetamine (PMA) usage amongst 'ecstasy' users indicates a proportionally greater incidence of acute toxicity compared to 3,4-methylenedioxymethamphetamine (MDMA). While longer-term use of MDMA appears to produce degeneration of 5-hydroxytryptamine (5-HT, serotonin) neurons, PMA effects are poorly understood.

In vivo analysis of serotonin clearance in rat hippocampus reveals that repeated administration of p-methoxyamphetamine (PMA), but not 3,4-methylenedioxymethamphetamine (MDMA), leads to long-lasting deficits in serotonin transporter function.

Paul D Callaghan et al.

Journal of neurochemistry, 100(3), 617-627 (2006-12-22)

p-Methoxyamphetamine (PMA) has been implicated in fatalities as a result of 'ecstasy' (MDMA) overdose worldwide. Like MDMA, acute effects are associated with marked changes in serotonergic neurotransmission, but the long-term effects of PMA are poorly understood. The aim of this

Trafficking properties and activity regulation of the neuronal glycine transporter GLYT2 by protein kinase C.

Amparo Fornés et al.

The Biochemical journal, 412(3), 495-506 (2008-03-18)

The neuronal glycine transporter GLYT2 controls the availability of the neurotransmitter in glycinergic synapses, and the modulation of its function may influence synaptic transmission. The active transporter is located in membrane rafts and reaches the cell surface through intracellular trafficking.

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