[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine

• ChemBase编号: 1257
• 分子式: C11H15NO2
• 平均质量: 193.2423
• 单一同位素质量: 193.11027873
• SMILES: O1c2cc(CC(NC)C)ccc2OC1
• Canonical SMILES: CNC(Cc1ccc2c(c1)OCO2)C
• 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
• InChIKey: SHXWCVYOXRDMCX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: [1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine
• IUPAC传统名: MDMA
• 别名: MDMA; Ecstasy; 3,4-Methylenedioxymethamphetamine; (±)-1,3-benzodioxolyl-N-methyl-2-propanamine(±)-3,4-methylenedioxy-N-methyl-α-methyl-2-phenethylamineDL-3,4-methylenedioxy-N-methylamphetaminemethylenedioxymethamphetamine; MDMA

登记号

• CAS号: 42542-10-9
• PubChem SID: 46506404; 160964717
• PubChem CID: 1615
• CHEBI ID: 1391
• CHEMBL: 43048
• Chemspider ID: 1556
• DrugBank ID: DB01454
• 美国药典/FDA物质标识码: KE1SEN21RM
• 维基百科标题: MDMA

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): -1.3648726
• LogD (pH = 7.4): -0.76064247
• Log P: 1.8600644
• 摩尔折射率: 54.2467 cm^3
• 极化性: 21.603132 Å^3
• 极化表面积: 30.49 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.65
• LOG S: -1.78
• 溶解度: 3.22e+00 g/l

分子性质

药理学性质

• 给药途径: Oral, sublingual, insufflation, inhalation (vaporization), injection, rectal
• 排泄: Renal
• 半衰期: 6–10 hours (though duration of effects is typically actually 3–5 hours)
• 代谢: Hepatic, CYP450 extensively involved, especially CYP2D6
• 法定药品分级: CD Lic (UK); S9 (Australia); Schedule I (US); Schedule III (Canada)
• 妊娠期药物分类: C

详细说明

DrugBank - DB01454

• Drug Groups: illicit; experimental
• Description: 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]
• Indication: 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.
• Pharmacology: MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
• Biotransformation: 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.
• Half Life: 6–10 (though duration of effects is typically actually 3–5 hours)
• Elimination: renal
• References: Freudenmann RW, Oxler F, Bernschneider-Reif S: The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5. [Pubmed] ; Jayanthi LD, Ramamoorthy S: Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAPS J. 2005 Oct 27;7(3):E728-38. [Pubmed]
• External Links: Wikipedia

参考文献

• Freudenmann RW, Oxler F, Bernschneider-Reif S: The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents. Addiction. 2006 Sep;101(9):1241-5. Pubmed
• Jayanthi LD, Ramamoorthy S: Regulation of monoamine transporters: influence of psychostimulants and therapeutic antidepressants. AAPS J. 2005 Oct 27;7(3):E728-38. Pubmed