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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO
Molecular Weight 165.2326
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-METHOXYAMPHETAMINE

SMILES

CC(Cc1ccc(cc1)OC)N

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 165.2326
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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 Fri Jun 25 21:03:25 UTC 2021
Edited
by admin
on Fri Jun 25 21:03:25 UTC 2021
Record UNII
OVB8F8P39Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-METHOXYAMPHETAMINE
Systematic Name English
FORMOTEROL FUMARATE RELATED COMPOUND G
USP  
Common Name English
D,L-P-METHOXYAMPHETAMINE
Common Name English
P-METHOXYAMPHETAMINE
Common Name English
(2RS)-1-(4-METHOXYPHENYL)PROPAN-2-AMINE
Systematic Name English
FORMOTEROL FUMARATE RELATED COMPOUND G [USP]
Common Name English
NSC-32757
Code English
4-METHOXYAMFETAMINE [MART.]
Common Name English
J213.549C
Code English
DR. DEATH
Common Name English
DEATH
Common Name English
4-METHOXYAMFETAMINE
MART.  
Common Name English
PARAMETHOXYAMPHETAMINE
Systematic Name English
P-METHOXYAMFETAMINE
Common Name English
4-MA-
Common Name English
J434.573H
Code English
PMA-
Common Name English
FORMOTEROL FUMARATE DIHYDRATE IMPURITY G [EP]
Common Name English
PARA-METHOXYAMPHETAMINE
Systematic Name English
Classification Tree Code System Code
DEA NO. 7411
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
Code System Code Type Description
EPA CompTox
64-13-1
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
EVMPD
SUB130947
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
MESH
C100230
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
CAS
23239-32-9
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
SUPERSEDED
DRUG BANK
DB01472
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
HSDB
7594
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
WIKIPEDIA
ppara-Methoxyamphetamine
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY para-Methoxyamphetamine (PMA; "Death", "Dr. Death"), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison,[citation needed] though it does have some psychedelic properties.
ECHA (EC/EINECS)
200-577-0
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
PUBCHEM
31721
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
FDA UNII
OVB8F8P39Q
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
CAS
64-13-1
Created by admin on Fri Jun 25 21:03:26 UTC 2021 , Edited by admin on Fri Jun 25 21:03:26 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
MINOR
METABOLITE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
The reporting threshold is? (IRA 1-Jan-2020) 0.05%
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY