66142-89-0

Basic information

• Product Name: (+)-MDMA
• Synonyms: (S)-N,α-Dimethyl-1,3-benzodioxole-5-ethanamine;[S,(+)]-N,α-Dimethyl-1,3-benzoxol-5-ethanamine;S-(+)-MDMA;(S)-(+)-3,4-(Methylenedioxy)methamphetamine;(S)-Methylenedioxymethamphetamine;(S)-N,alpha-Dimethyl-1,3-benzodioxole-5-ethanamine
• CAS NO: 66142-89-0
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Mol File: 66142-89-0.mol

Chemical Properties

• Boiling Point: 283 ºC
• Flash Point: 113 ºC
• Appearance: /
• Density: 1.100
• PKA: 10.32±0.10(Predicted)
• CAS DataBase Reference: (+)-MDMA(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-MDMA(66142-89-0)
• EPA Substance Registry System: (+)-MDMA(66142-89-0)

Safety Data

• Hazardous Substances Data: 66142-89-0(Hazardous Substances Data)

Usage

Uses

Used in Recreational Settings:
(+)-MDMA is used as a recreational drug for its ability to induce feelings of euphoria, increased sociability, and heightened sensory perception. It is popular in party settings due to these effects.
Used in Therapeutic Research:
(+)-MDMA is used as a subject of research in the field of mental health treatment. It is being explored for its potential to treat conditions such as PTSD and other mental health disorders, due to its effects on neurotransmitter release in the brain.
Used in Pharmaceutical Development:
(+)-MDMA is used as a compound in the development of new pharmaceuticals, with the aim of harnessing its effects on neurotransmitters for therapeutic purposes, while mitigating the associated health risks.

Upstream product

• 440367-00-0 (S)-N-ethoxycarbonyl-1-(3,4-methylenedihydroxyphenyl)-2-aminopropane 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 36593-29-0 1-(3,4-bis(benzyloxy)phenyl)propan-2-amine 
• 62932-96-1 1-(3,4-dibenzyloxyphenyl)-2-nitropropene 
• 440366-97-2 (S)-1-(3,4-bis(benzyloxy)phenyl)propan-2-amine 
• 440366-99-4 (S)-N-ethoxycarbonyl-1-(3,4-dihydroxyphenyl)-2-aminopropane 
• 440366-92-7 (S)-N-ethoxycarbonyl-1-(3,4-dibenzyloxyphenyl)-2-aminopropane 
• 65620-66-8 (+)-Tenamfetamine 
• 62932-96-1 (E)-1,2-dibenzyloxy-4-(2-nitroprop-1-en-1-yl)benzene 
• 62932-76-7 1-(3,4-bis(benzyloxy)phenyl)propan-2-one 
• 1616297-04-1 (S,S_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]tertbutylsulfinamide 
• 42542-10-9 3,4-methylenedioxymethamphetamine 
• 4764-17-4 (-)-Tenamfetamine 
• 1616297-02-9 (R)-ethyl [1-(3,4-dihydroxyphenyl)propan-2-yl]carbamate 

Downstream Products

• 65620-66-8 (+)-Tenamfetamine 
• 131206-60-5 S-(+)-3,4-methylenedioxy-N,N-dimethylamphetamine 
• 4764-17-4 (-)-Tenamfetamine 

Relevant articles and documents

Chiral separation of cathinone and amphetamine derivatives by HPLC/UV using sulfated β-cyclodextrin as chiral mobile phase additive

In the last years the identification of new legal and illegal highs has become a huge challenge for the police and prosecution authorities. In an analytical context, only a few analytical methods are available to identify these new substances. Moreover, many of these recreational drugs are chiral and it is supposed that the enantiomers differ in their pharmacological potency. Since nonenantioselective synthesis is easier and cheaper, they are mainly sold as racemic mixtures. The goal of this research work was to develop an inexpensive method for the chiral separation of cathinones and amphetamines. This should help to discover if the substances are sold as racemic mixtures and give further information about their quality as well as their origin. Chiral separation of a set of 6 amphetamine and 25 cathinone derivatives, mainly purchased from various Internet shops, is presented. A LiChrospher 100 RP-18e, 250 x 4 mm, 5 μm served as the stationary phase. The chiral mobile phase consisted of methanol, water, and sulfated β-cyclodextrin. Measurements were performed under isocratic conditions in reversed phase mode using UV detection. Four model compounds of the two substance classes were used to optimize the mobile phase. Under final conditions (methanol:water 2.5:97.5 + 2% sulfated β-cyclodextrin) enantiomers of amphetamine and five derivatives were baseline separated within 23 min. In all, 17 cathinones were completely or partially chirally separated. However, as only 3 of 25 cathinones were baseline resolved, the application of this method is limited for cathinone analogs. Additionally, the results were compared with an RP-8e column. Copyright

Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: Synthesis, pharmacological evaluation and mechanistic studies

The α4β2 nicotinic acetylcholine receptor (nAChR) is a molecular target of 3,4-methylenedioxymethamphetamine (MDMA), a synthetic drug also known as ecstasy, and it modulates the MDMA-mediated reinforcing properties. However, the enantioselective preference of the α4β2 nAChR subtype still remains unknown. Since the two enantiomers exhibit different pharmacological profiles and stereoselective metabolism, the aim of this study is to assess a possible difference in the interaction of the MDMA enantiomers with this nAChR subtype. To this end, we report a novel simple, yet highly efficient enantioselective synthesis of the MDMA enantiomers, in which the key step is the diastereoselective reduction of imides derived from optically pure tert-butylsulfinamide. The enantioselective binding to the receptor is examined using [3H]epibatidine in a radioligand assay. Even though the two enantiomers induced a concentration-dependent binding displacement, (S)-MDMA has an inhibition constant 13-fold higher than (R)-MDMA, which shows a Hill's coefficient not significantly different from unity, implying a competitive interaction. Furthermore, when NGF-differentiated PC12 cells were pretreated with the compounds, a significant increase in binding of [3H] epibatidine was found for (R)-MDMA, indicating up-regulation of heteromeric nAChR in the cell surface. Finally, docking and molecular dynamics studies have been used to identify the binding mode of the two enantiomers, which provides a structural basis to justify the differences in affinity from the differential interactions played by the substituents at the stereogenic centre of MDMA. The results provide a basis to explore the distinct psychostimulant profiles of the MDMA enantiomers mediated by the α4β2 nAChR subtype.

Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites

Enantiomerically-enriched (S)-3,4-methylenedioxymethamphetamine (MDMA) and its main metabolites (S)-4-hydroxy-3-methoxymethamphetamine (HMMA) and (S)-3,4-dihydroxymethamphetamine (HHMA) were prepared or unequivocal identification of the differential enantioselective metabolism of these compounds as well as for its application in the analysis of biological samples. Capillary electrophoresis with cyclodextrin derivatives and a chemical correlation of (S)-MDMA, (S)-HMMA and (S)-HHMA has been performed to assign the absolute stereochemistry of major isomers in analytical standards enriched with such enantiomers. Copyright

Stereoselective synthesis of (s)-3,4-methylenedioxyamphetamines from (r)-cyanohydrins

A stereoselective synthesis of (S)-3,4-methylenedioxyamphetamines (S)-7, which are highly interesting as psychoactive compounds, is described. Starting from readily available (R)-cyanohydrins (R)-2 the 2-amino-1-aryl alcohols (1R,2S)-4 were obtained with

Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class

The α-ethyl phenethylamine derivative 1-(1,3-benzodioxol-5-yl)-2-butanamine was prepared. An asymmetric synthesis was used to prepare the enantiomers of this compound and the related α-methyl homologue (MDA). The racemates and enantiomers of both compounds were evaluated in the two-lever drug discrimination assay in rats trained to discriminate saline from 0.08 mg/kg of LSD tartrate. Stimulus generalization occurred with the racemate and the R-(-)enantiomer of the α-methyl homologue and the S-(+)enantiomer of the α-ethyl primary amine. No generalization occurred with the other enantiomers or with the N-methyl derivatives of either series. Human psychopharmacology studies revealed that the N-methyl derivative of the title compound was nonhallucinogenic and that it had a new, novel psychoactive effect. It is suggested that this compound is the prototype of a new pharmacologic class that may have value in facilitating psychotherapy and that this class be designated as entactogens.