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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO
Molecular Weight 165.2322
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHOXYAMPHETAMINE

SMILES

COC1=CC=C(CC(C)N)C=C1

InChI

InChIKey=NEGYEDYHPHMHGK-UHFFFAOYSA-N
InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C10H15NO
Molecular Weight 165.2322
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

4-Methoxyamphetamine (Para-methoxyamphetamine, PMA) is a synthetic drug chemically similar to the recreational drug 3,4-methylenedioxymethamphetamine (MDMA or "ecstasy") and often replaces MDMA in tablets. Numerous cases of intoxication have been documented and fatal cases involving PMA have been described. PMA induces toxicity at lower doses than MDMA. Clinical symptoms specific to PMA poisoning include life-threatening hyperthermia, breathing difficulties, tachycardia, rhabdomyolysis, and acute renal failure. In the scarce studies conducted in laboratory animals, PMA has shown cardiovascular alterations in dogs, hyperthermia on a high ambient temperature, hallucinogen properties, and disruption of operant behavior in rats. A slight motor activity stimulation, lower than that induced by MDMA, has also been reported. The effects of PMA on brain neurotransmission are similar to those of MDMA, thus, PMA increases serotonin (5-hydroxytryptophan or 5-HT) release from the synaptic terminal and blocks its reuptake; it also acts upon noradrenergic and dopaminergic terminals but in a lesser proportion, and can also delay the metabolism of these monoamines by inhibition of monoamine oxidase (MAO)

Approval Year

PubMed

Substance Class Chemical
Record UNII
OVB8F8P39Q
Record Status Validated (UNII)
Record Version