PMID- 30001118
OWN - NLM
STAT- MEDLINE
DCOM- 20191118
LR  - 20230928
IS  - 1948-7193 (Electronic)
IS  - 1948-7193 (Linking)
VI  - 9
IP  - 10
DP  - 2018 Oct 17
TI  - Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine.
PG  - 2408-2427
LID - 10.1021/acschemneuro.8b00155 [doi]
AB  - Better known as "ecstasy", 3,4-methylenedioxymethamphetamine (MDMA) is a small 
      molecule that has played a prominent role in defining the ethos of today's 
      teenagers and young adults, much like lysergic acid diethylamide (LSD) did in the 
      1960s. Though MDMA possesses structural similarities to compounds like 
      amphetamine and mescaline, it produces subjective effects that are unlike any of 
      the classical psychostimulants or hallucinogens and is one of the few compounds 
      capable of reliably producing prosocial behavioral states. As a result, MDMA has 
      captured the attention of recreational users, the media, artists, psychiatrists, 
      and neuropharmacologists alike. Here, we detail the synthesis of MDMA as well as 
      its pharmacology, metabolism, adverse effects, and potential use in medicine. 
      Finally, we discuss its history and why it is perhaps the most important compound 
      for the future of psychedelic science-having the potential to either facilitate 
      new psychedelic research initiatives, or to usher in a second Dark Age for the 
      field.
FAU - Dunlap, Lee E
AU  - Dunlap LE
AD  - Department of Chemistry , University of California, Davis , One Shields Avenue , 
      Davis , California 95616 , United States.
FAU - Andrews, Anne M
AU  - Andrews AM
AUID- ORCID: 0000-0002-1961-4833
AD  - Departments of Psychiatry and Chemistry & Biochemistry, Semel Institute for 
      Neuroscience and Human Behavior, and Hatos Center for Neuropharmacology , 
      University of California , Los Angeles , California 90095 , United States.
FAU - Olson, David E
AU  - Olson DE
AUID- ORCID: 0000-0002-4517-0543
AD  - Department of Chemistry , University of California, Davis , One Shields Avenue , 
      Davis , California 95616 , United States.
AD  - Department of Biochemistry & Molecular Medicine, School of Medicine , University 
      of California, Davis , 2700 Stockton Blvd, Suite 2102 , Sacramento , California 
      95817 , United States.
AD  - Center for Neuroscience , University of California, Davis , 1544 Newton Ct , 
      Davis , California 95616 , United States.
LA  - eng
GR  - R01 DA045550/DA/NIDA NIH HHS/United States
PT  - Historical Article
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, Non-U.S. Gov't
PT  - Review
DEP - 20180712
PL  - United States
TA  - ACS Chem Neurosci
JT  - ACS chemical neuroscience
JID - 101525337
RN  - 0 (Hallucinogens)
RN  - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine)
SB  - IM
MH  - Hallucinogens/*chemistry/history/*pharmacology/therapeutic use
MH  - History, 20th Century
MH  - History, 21st Century
MH  - Humans
MH  - N-Methyl-3,4-methylenedioxyamphetamine/*chemistry/history/*pharmacology/therapeutic 
      use
PMC - PMC6197894
MID - NIHMS982919
OTO - NOTNLM
OT  - 3,4-methylenedioxymethamphetamine
OT  - MDMA
OT  - empathogen
OT  - entactogen
OT  - psychedelic
EDAT- 2018/07/13 06:00
MHDA- 2019/11/19 06:00
PMCR- 2018/10/22
CRDT- 2018/07/13 06:00
PHST- 2018/07/13 06:00 [pubmed]
PHST- 2019/11/19 06:00 [medline]
PHST- 2018/07/13 06:00 [entrez]
PHST- 2018/10/22 00:00 [pmc-release]
AID - 10.1021/acschemneuro.8b00155 [doi]
PST - ppublish
SO  - ACS Chem Neurosci. 2018 Oct 17;9(10):2408-2427. doi: 
      10.1021/acschemneuro.8b00155. Epub 2018 Jul 12.