Tìm theo
3,4-Methylenedioxymethamphetamine
Các tên gọi khác (2) :
  • Ecstasy
  • MDMA
Thuốc Gốc
Small Molecule
CAS: 42542-10-9
CTHH: C11H15NO2
PTK: 193.2423
An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C11H15NO2
Phân tử khối
193.2423
Monoisotopic mass
193.110278729
InChI
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
InChI Key
InChIKey=SHXWCVYOXRDMCX-UHFFFAOYSA-N
IUPAC Name
[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
Traditional IUPAC Name
MDMA
SMILES
CNC(C)CC1=CC2=C(OCO2)C=C1
Độ hòa tan
3.22e+00 g/l
logP
1.86
logS
-1.8
pKa (Strongest Basic)
10.14
PSA
30.49 Å2
Refractivity
54.25 m3·mol-1
Polarizability
21.49 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
1
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
Cơ Chế Tác Dụng : An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. [PubChem] 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.
Dược Động Học :

▧ Metabolism :
Hepatic: CYP450 extensively involved, especially CYP2D6 MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 (CYP450) enzymes (CYP2D6 (in humans, but CYP2D1 in mice), and CYP3A4) and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics 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.
▧ Route of Elimination :
renal
▧ Half Life :
6–10 (though duration of effects is typically actually 3–5 hours)
Chỉ Định : Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01454
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=1615
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506404
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07577
ChemSpider
http://www.chemspider.com/Chemical-Structure.1556.html
PharmGKB
http://www.pharmgkb.org/drug/PA131887008
Wikipedia
http://en.wikipedia.org/wiki/3,4-Methylenedioxymethamphetamine
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