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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO.ClH
Molecular Weight 201.693
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHOXYAMFETAMINE HYDROCHLORIDE

SMILES

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

InChI

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

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

PubMed

TitleDatePubMed
Effects of para-methoxyamphetamine (PMA) on agonistic encounters between male mice.
2018 Apr
Substance Class Chemical
Created
by admin
on Sat Dec 16 19:07:24 UTC 2023
Edited
by admin
on Sat Dec 16 19:07:24 UTC 2023
Record UNII
5P66783GRV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-METHOXYAMFETAMINE HYDROCHLORIDE
Common Name English
2-AMINO-1-(4-METHOXYPHENYL)PROPANE HYDROCHLORIDE
Systematic Name English
PHENETHYLAMINE, P-METHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE
Systematic Name English
4-MA hydrochloride
Common Name English
BENZENEETHANAMINE, 4-METHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE
Systematic Name English
(±)-4-METHOXYAMPHETAMINE HYDROCHLORIDE
Systematic Name English
para-Methoxyamphetamine hydrochloride
Common Name English
BENZENEETHANAMINE, 4-METHOXY-.ALPHA.-METHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
P-METHOXYAMPHETAMINE HYDROCHLORIDE
Common Name English
PMA (PSYCHEDELIC) hydrochloride
Common Name English
PMA hydrochloride
Common Name English
4-METHOXYAMPHETAMINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
CAYMAN
12041
Created by admin on Sat Dec 16 19:07:25 UTC 2023 , Edited by admin on Sat Dec 16 19:07:25 UTC 2023
PRIMARY
FDA UNII
5P66783GRV
Created by admin on Sat Dec 16 19:07:25 UTC 2023 , Edited by admin on Sat Dec 16 19:07:25 UTC 2023
PRIMARY
PUBCHEM
135236
Created by admin on Sat Dec 16 19:07:25 UTC 2023 , Edited by admin on Sat Dec 16 19:07:25 UTC 2023
PRIMARY
CAS
3706-26-1
Created by admin on Sat Dec 16 19:07:25 UTC 2023 , Edited by admin on Sat Dec 16 19:07:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID10958225
Created by admin on Sat Dec 16 19:07:25 UTC 2023 , Edited by admin on Sat Dec 16 19:07:25 UTC 2023
PRIMARY
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ACTIVE MOIETY