42542-10-9

Basic information

• Product Name: (+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE
• Synonyms: (+/-)-MDMA;DL-MDMA;AURORA KA-7748;(+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE;3,4-MDMA;1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine;1,3-Benzodioxole-5-ethanamine, N,alpha-dimethyl-;3,4-Methylenedioxymethylamphetamine
• CAS NO: 42542-10-9
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 200-659-6
• Product Categories: 42542-10-9 MDMA
• Mol File: 42542-10-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: bp0.4 100-110°
• Flash Point: 9℃
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 0.000272mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 10.32±0.10(Predicted)
• CAS DataBase Reference: (+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE(42542-10-9)
• EPA Substance Registry System: (+/-)-3,4-METHYLENEDIOXYMETHAMPHETAMINE(42542-10-9)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 42542-10-9(Hazardous Substances Data)

Usage

Definition

ChEBI: A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.

Metabolic pathway

Four biotransformation pathways of 3,4- (methylenedioxy)methamphetamine (MDMA) in rats are identified as N-demethylation, O-dealkylation, deamination, and conjugation (O-methylation, O- glucuronidation, and/or sulfation). Specific MDMA metabolites identified are 3-hydroxy-4- methoxymethamphetamine, 4-hydroxy-3- methoxymethamphetamine, 3,4- dihydroxymethamphetamine, 4-hydroxy-3- methoxyamphetamine, 3,4- (methylenedioxy)amphetamine (MDA), (4-hydroxy-3- methoxyphenyl)acetone, [3,4- (methylenedioxy)phenyl]acetone, and (3,4- dihydroxyphenyl)acetone. MDMA is metabolized by 10 000 g rat liver supernatant to 4-hydroxy-3- methoxymethamphetamine, 3,4- dihydroxymethamphetamine, MDA, and [3,4- (methylenedioxy)phenyl]acetone. Also, the 10 000 g rat brain supernatant metabolizes MDMA to 4-hydroxy- 3-methoxymethamphetamine, 3,4- dihydroxymethamphetamine, 4-hydroxy-3- methoxyamphetamine, and MDA.

InChI:InChI=1/C11H15NO2.ClH/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;1H/t8-;/m0./s1

Upstream product

• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 593-51-1 methylamine hydrochloride 
• 74-89-5 methylamine 
• 1228259-70-8 tert-butyl N-{3-(3,4-methylenedioxyphenyl)-2-propyl}-N-methylcarbamate 
• 42542-10-9 3,4-methylenedioxymethamphetamine 
• 4764-17-4 (-)-Tenamfetamine 
• 5438-41-5 5-(2-nitroprop-1-enyl)benzo[d][1,3]dioxole 
• 120-57-0 piperonal 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 1616297-01-8 (R)-ethyl [1-(3,4-dibenzyloxyphenyl)propan-2-yl]carbamate 
• 1616296-98-0 (R,R_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]tertbutylsulfinamide 
• 62932-76-7 1-(3,4-bis(benzyloxy)phenyl)propan-2-one 
• 62932-96-1 (E)-1,2-dibenzyloxy-4-(2-nitroprop-1-en-1-yl)benzene 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 

Downstream Products

• 154148-22-8 N-(2-benzo[1,3]dioxol-5-yl-1-methylethyl)-N-methylformamide 
• 4764-17-4 3,4-methylenedioxyamphetamine 
• 15398-87-5 (+/-)-DHMA 
• 66142-89-0 (S)-3,4-methylenedioxymethamphetamine 
• 42542-10-9 (-)-3,4-Methylenedioxymethamphetamine 
• 30223-73-5 (R,S)-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine 
• 4764-17-4 (-)-Tenamfetamine 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 6543-34-6 benzo[1,3]dioxol-5-yl-acetaldehyde 

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

Synthesis of 2-Arylethylamines by the Curtius Rearrangement

2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield. Copyright Taylor & Francis Group, LLC.

Pharmacological characterization of ecstasy synthesis byproducts with recombinant human monoamine transporters

Ecstasy samples often contain byproducts of the illegal, uncontrolled synthesis of N-methyl-3,4-methylenedioxy-amphetamine or 3,4-methylenedioxy- methamphetamine (MDMA). MDMA and eight chemically defined byproducts of MDMA synthesis were investigated for their interaction with the primary sites of action of MDMA, namely the human plasmalemmal monamine transporters for norepinephrine, serotonin, and dopamine [(norepinephrine transporter (NET), serotonin transporter (SERT), and dopamine transporter (DAT)]. SKN-MC neuroblastoma and human embryonic kidney cells stably transfected with the transporter cDNA were used for uptake and release experiments. Two of the eight compounds, 1,3-bis (3,4-methylenedioxyphenyl)-2-propanamine (12) and N-formyl-1,3-bis (3,4-methylenedioxyphenyl)-prop-2-yl-amine (13) had uptake inhibitory potencies with IC50 values in the low micromolar range similar to MDMA. Compounds with nitro instead of amino groups and a phenylethenyl instead of a phenylethyl structure or a formamide or acetamide modification had IC50 values beyond 100 μM. MDMA, 12, and 13 were examined for induction of carrier-mediated release by superfusion of transporter expressing cells preloaded with the metabolically inert transporter substrate [3H]1-methyl-4-phenylpyridinium. MDMA induced release mediated by NET, SERT, or DAT with EC50 values of 0.64, 1.12, and 3.24 μM, respectively. 12 weakly released from NET- and SERT-expressing cells with maximum effects less than one-tenth of that of MDMA and did not release from DAT cells. 13 had no releasing activity. 12 and 13 inhibited release induced by MDMA, and the concentration dependence of this effect correlated with their uptake inhibitory potency at the various transporters. These results do not support a neurotoxic potential of the examined ecstasy synthesis byproducts and provide interesting structure-activity relationships on the transporters. Copyright