General
Preferred name
Midomafetamine
Synonyms
MDMA ()
METHYLENEDIOXYMETHAMPHETAMINE ()
MIDOMAFETAMINE HYDROCHLORIDE ()
3,4-MDMA (hydrochloride) ()
3,4-MDMA-d3 (hydrochloride) ()
3,4-MDMA-d5 (hydrochloride) (CRM) ()
Mdma hydrochloride ()
Mdma hcl ()
NSC-168383 ()
Mandy ()
Methylenedioxymethamphetamine ()
Midomafetamina ()
3,4-methylenedioxymetamphetamine ()
Ecstasy ()
Methylenedioxymethamfetamine ()
3,4-Methylenedioxymethamphetamine ()
Molly ()
Methylenedioxy Methamphetamine ()
Methylenedioxymetamphetamine ()
Mdma ()
3,4-MDMA-d5 (hydrochloride) ()
3,4-MDMA-d5 (hydrochloride) (CRM) ()
P&D ID
PD008854
CAS
42542-10-9
69610-10-2
64057-70-1
1219794-60-1
2747917-97-9
Tags
available
drug candidate
Drug indication
Discovery agent
Post-traumatic stress disorder
Drug Status
investigational
experimental
illicit
Max Phase
3.0
1.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
It enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylation. It also acts as a weak 5-HT1 and 5-HT2 receptor agonist.; MDMA's unusual entactogenic effects have been hypothesized to be, at least partly, the result of indirect oxytocin secretion via activation of the serotonin system. Oxytocin is a hormone released following events like hugging, orgasm, and childbirth, and is thought to facilitate bonding and the establishment of trust. Based on studies in rats, MDMA is believed to cause the release of oxytocin, at least in part, by both directly and indirectly agonizing the serotonin 5-HT1A receptor.
DESCRIPTION
MDMA has psychoactive effects.
(GtoPdb)
METABOLISM
Midomafetamine, or MDMA, is reported to undergo extensive CYP-mediated hepatic metabolism, with CYP2D6 playing a major role in humans. Other CYP enzymes contributing to MDMA metabolism are CYP3A4 and COMT. ; MDMA is metabolized via two primary metabolic pathways. It may undergo O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation. In contrast, it may also undergo N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. Due to autoinhibition of CYP2D6 and CYP2D8, MDMA displays a complex, nonlinear pharmacokinetics profile, with the zeroth order kinetics occurring at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
1
Organisms
0
Compound Sets
10
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugMAP
Guide to Pharmacology
Ki Database
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
48
Molecular Weight
193.11
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
2
Aromatic Ring Count
1
cLogP
1.57
TPSA
30.49
Fraction CSP3
0.45
Chiral centers
1.0
Largest ring
6.0
QED
0.79
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Source data
