3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.
MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population). This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids. In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year. The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances.
Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat, and extended use can also lead to addiction, memory problems, paranoia, and difficulty sleeping. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel depressed and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration. MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It belongs to the substituted amphetamine classes of drugs. MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.
MDMA has limited approved medical uses in a small number of countries, but is illegal in most jurisdictions. In the United States, the Food and Drug Administration (FDA) is evaluating the drug for clinical use as of 2021. Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada. In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.
|
Read full article at Wikipedia
|
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3 |
SHXWCVYOXRDMCX-UHFFFAOYSA-N |
|
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
|
|
neurotoxin
A poison that interferes with the functions of the nervous system.
|
|
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
(via amphetamines )
|
|
View more via ChEBI Ontology
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
|
(RS)-3,4-(methylenedioxy)methamphetamine
|
ChemIDplus
|
1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine
|
NIST Chemistry WebBook
|
3,4-Methylenedioxymethamphetamine
|
KEGG COMPOUND
|
DL-(3,4-Methylenedioxy)methamphetamine
|
ChemIDplus
|
ecstasy
Note: (2016-06-20) The name "ecstasy" is no longer used only for MDMA, but for the whole group of ring-substituted amphetamines (RSAs) including MDA, MDMA, MDEA and MBDB, as they are chemically and pharmacologically nearly identical; moreover, many ecstasy pills contain mixtures of the RSAs. |
|
ChEBI
|
MDMA
|
KEGG COMPOUND
|
MDMA
|
ChemIDplus
|
N,α-dimethyl-1,3-benzodioxole-5-ethanamine
|
NIST Chemistry WebBook
|
N-Methyl-3,4-methylenedioxyamphetamine
|
KEGG COMPOUND
|
158675
|
Reaxys Registry Number
|
Reaxys
|
42542-10-9
|
CAS Registry Number
|
KEGG COMPOUND
|
42542-10-9
|
CAS Registry Number
|
ChemIDplus
|
Beuerle JR, Barrueto F (2008) Neurogenic bladder and chronic urinary retention associated with MDMA abuse. Journal of medical toxicology : official journal of the American College of Medical Toxicology 4, 106-108 [PubMed:18570171] [show Abstract]
IntroductionThe use of 3,4-methylenedioxymethamphetamine (MDMA, known as "ecstasy"), a synthetic amphetamine and "club drug," has been associated with acute, transient urinary retention. We report a case of neurogenic bladder and chronic urinary retention associated with MDMA abuse.Case reportA 21-year-old male presented to the emergency department (ED) because he had abdominal pain and difficulty urinating. He had experienced difficulty in initiating urination over the past 1.5 months, with periods of 24 to 36 hours between voids and large volumes of urine. The patient had a chronic pattern of MDMA use, taking 4 tablets/day for 3 months. Two weeks before coming to the ED, he had been admitted to an inpatient drug rehabilitation center. During the time since that admission, the patient had visited EDs repeatedly for insertion and removal of Foley catheters to relieve the urinary retention until he could be admitted to a urologic service. Cystometrogram was abnormal, finding no sensation of bladder fullness after instillation of 350 mL of saline and inability to generate a voluntary voiding pressure. Cystoscopy revealed no outlet obstruction. The findings were consistent with neurogenic bladder. The patient was given prescriptions for bethanecol and phenazopyridine, and told to continue a 10-day course of sulfamethoxazole/trimethoprim for urinary tract infection. He was discharged with a Foley catheter in place. Symptoms of urinary retention persisted at 1-year follow-up, despite self-catheterization and complete cessation of MDMA use.ConclusionChronic MDMA use may lead to neurogenic bladder and chronic urinary retention. | De Letter EA, Bouche MP, Van Bocxlaer JF, Lambert WE, Piette MH (2004) Interpretation of a 3,4-methylenedioxymethamphetamine (MDMA) blood level: discussion by means of a distribution study in two fatalities. Forensic science international 141, 85-90 [PubMed:15062945] [show Abstract] The amphetamine derivative 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy" is a currently used or abused designer drug and fatalities are frequently encountered in forensic practice. However, the question remains open whether an MDMA blood level can be toxic or even potentially lethal. In order to provide insight in the interpretation of a detected MDMA concentration, the distribution of MDMA and its metabolite 3,4-methylenedioxyamphetamine (MDA) in various body fluids and tissues was studied and discussed in two different fatalities. Apart from peripheral blood samples (such as femoral and subclavian blood), various blood samples obtained centrally in the human body and several body fluids (such as vitreous humour) were examined. In addition, various tissues such as cardiac muscle, lungs, liver, kidneys, and brain lobes were analysed. In contrast to the peripheral blood levels, high MDMA and MDA levels were found in cardiac blood and the majority of the organs, except for the abdominal adipose tissue. The high concentrations observed in all lung lobes, the liver and stomach contents indicate that post-mortem redistribution of MDMA and MDA into cardiac blood can occur and, as a result, blood sampled centrally in the body should be avoided. Therefore, our data confirm that peripheral blood sampling remains "the golden standard". In addition, a distinct difference in peripheral blood MDMA concentrations in our two overdose cases was established (namely 0.271 and 13.508 microg/ml, respectively). Furthermore, our results suggest that, if a peripheral blood sample is not available and when putrefaction is not too pronounced, vitreous humour and iliopsoas muscle can be valuable specimens for toxicological analysis. Finally, referring to the various mechanisms of death following amphetamine intake, which can result in different survival times (e.g. cardiopulmonary complications versus hyperthermia), the anatomo-pathological findings and the toxicological results should be considered as a whole in arriving at a conclusion. |
|