(+/-)-N-Methyl-3,4-(methylenedioxy)amphetamine

HCID 1615

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Basic information

CAS: 42542-10-9
Standard SMILES: CNC(C)Cc1ccc2c(c1)OCO2
InChIKey: SHXWCVYOXRDMCX-UHFFFAOYSA-N
Molecular formula: C11H15NO2
Average molar mass: 193.246 g/mol
Monoisotopic mass: 193.11027872

Names & identifiers

Preferred name: (+/-)-N-Methyl-3,4-(methylenedioxy)amphetamine
IUPAC: 1-(2H-1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine
English name: (+/-)-3,4-Methylenedioxymethamphetamine
Molecular formula: C11H15NO2
Molecular weight: 193.25

Names & synonyms

MethylenedioxymethamphetamineXTC3,4-MDMA3,4-MethylenedioxymethylamphetamineC07577DL-MDMAecstacy(+/-)-MDMAGMP 3,4-MDMAAURORA KA-7748

Database identifiers

CAS: 42542-10-9
PubChem CID: 1615
DTXSID: DTXSID90860791
ChEMBL: CHEMBL43048
ChEBI: CHEBI:1391
UNII: KE1SEN21RM
EC Number: 980-806-5
Nikkaji: J276.360E

Properties

Physicochemical properties

Boiling point: 0.4 · bp0.4 100-110°
Density: 1.1 · 1.100±0.06 g/cm3(Predicted)
Flash point: 9 ℃ · 9℃
storage temp.: 2 · 2-8°C
pka: 10.32 · 10.32±0.10(Predicted)
InChIKey: SHXWCVYOXRDMCX-UHFFFAOYSA-N
EWG's Food Scores: 1 · 1
FDA UNII: 1 SEN21RM · KE1SEN21RM
NCI Drug Dictionary: 3 · 3,4-methylenedioxymethamphetamine
EPA Substance Registry System: 1 · 1,3-Benzodioxole-5-ethanamine, N,.alpha.-dimethyl- (42542-10-9)
Symbol(GHS): 2 · GHS02,GHS06,GHS08
Signal word: Danger
Hazard statements: 225 · H225-H301+H311+H331-H370
Precautionary statements: 210 · P210-P260-P280-P301+P310-P311
Hazard Codes: F,T
Risk Statements: 11 · 11-23/24/25-39/23/24/25
Safety Statements: 7 · 7-16-36/37-45
RIDADR: 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany: 1 · 1
Hazardous Substances Data: 42542 · 42542-10-9(Hazardous Substances Data)
Toxicity: 50 is · A novel psychoactive drug chemically related to the hallucinogenic agent MDA, but reported to be non-hallucinogenic. Obtained by direct synthesis, at high doses it is reported to show a stimulant-like effect in animals. Its LD50 is 97 mg/kg, i. p., 49 mg/kg, i.p., 14 mg/kg, i.v., and 22 mg/kg, i.v. in mice, rats, dogs, and monkeys, respectively. At higher doses, MDMA has pressor effects and produces tachycardia, and causes damage to serotonin neurons in both rats and monkeys. The (S)- (1)-enantiomer is more active than the (R)-(′)-enantiomer and, like amphetamine, the pharmacological effects may be due to a release of endogenous monoamine neurotransmitter, probably serotonin and/or norepinephrine. MDMA is also an inhibitor of monoamine uptake into brain synaptosomes. Symptoms include pronounced mydriasis, with nystagmus and jaw clenching, and nausea also is often reported. This substance produces a feeling of well-being and euphoria and is similar in some respects to MDA, in that it seems to enhance a sense of empathy and emotional openness in users. Toxic reactions would appear to occur as a result of the pressor action, and sympathomimetic effects of the drug. No appropriate therapeutic intervention has been reported. Peripheral adrenergic blocking agents, or chlorpromazine, have been used, however, to prevent death in dogs following a lethal i.v. dose of the chemically related agent MDA.

Safety & regulation

Safety data

wgk: 1
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
Toxicity: A novel psychoactive drug chemically related to the hallucinogenic agent MDA, but reported to be non-hallucinogenic. Obtained by direct synthesis, at high doses it is reported to show a stimulant-like effect in animals. Its LD50 is 97 mg/kg, i. p., 49 mg/kg, i.p., 14 mg/kg, i.v., and 22 mg/kg, i.v. in mice, rats, dogs, and monkeys, respectively. At higher doses, MDMA has pressor effects and produces tachycardia, and causes damage to serotonin neurons in both rats and monkeys. The (S)- (1)-enantiomer is more active than the (R)-(′)-enantiomer and, like amphetamine, the pharmacological effects may be due to a release of endogenous monoamine neurotransmitter, probably serotonin and/or norepinephrine. MDMA is also an inhibitor of monoamine uptake into brain synaptosomes. Symptoms include pronounced mydriasis, with nystagmus and jaw clenching, and nausea also is often reported. This substance produces a feeling of well-being and euphoria and is similar in some respects to MDA, in that it seems to enhance a sense of empathy and emotional openness in users. Toxic reactions would appear to occur as a result of the pressor action, and sympathomimetic effects of the drug. No appropriate therapeutic intervention has been reported. Peripheral adrenergic blocking agents, or chlorpromazine, have been used, however, to prevent death in dogs following a lethal i.v. dose of the chemically related agent MDA.
risk_code: 11-23/24/25-39/23/24/25
Signal word: Danger
Symbol(GHS): GHS02,GHS06,GHS08
hazard_code: F,T
safety_code: 7-16-36/37-45
Hazard statements: H225-H301+H311+H331-H370
Precautionary statements: P210-P260-P280-P301+P310-P311
Hazardous Substances Data: 42542-10-9(Hazardous Substances Data)

Chemistry & industry

Applications

Uses3,4-Methylenedioxymethamphetamine (MDMA) is an Entactogen; It is the N-methyl derivative of MDA. The (S)-form of MDMA possesses more potent CNS activity than the (R) form of MDMA.MDMA is controlled substance (hallucinogen).