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N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine, commonly known as MMDA, is a psychoactive chemical compound that belongs to the amphetamine class. It is a derivative of the hallucinogenic drug MDA and shares structural similarities with MDMA (ecstasy). MMDA is recognized for its empathogenic and entactogenic effects, which include increased feelings of empathy, emotional closeness, and sensory enhancement. Its potential applications in psychotherapy and as a research tool for understanding the neurobiological underpinnings of empathy and emotional perception have been explored. However, due to its psychoactive properties and potential for abuse, MMDA is a controlled substance in many countries.

81262-69-3

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81262-69-3 Usage

Uses

Used in Psychotherapy:
MMDA is used as a therapeutic agent for its potential to enhance emotional closeness and empathy during psychotherapy sessions. It may facilitate deeper emotional connections and self-exploration, aiding in the treatment of various psychological conditions.
Used in Neurobiological Research:
In the field of neurobiology, MMDA serves as a research tool to investigate the mechanisms of empathy and emotional perception. Its effects on the brain can provide insights into the neural pathways involved in these processes, contributing to a better understanding of related psychological phenomena.
Used in Controlled Substances Regulation:
Due to its psychoactive properties and potential for abuse, MMDA is used in the context of controlled substances regulation. Its classification and monitoring are essential for public health and safety, ensuring that its use is limited to appropriate settings and preventing misuse.

Check Digit Verification of cas no

The CAS Registry Mumber 81262-69-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,2,6 and 2 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 81262-69:
(7*8)+(6*1)+(5*2)+(4*6)+(3*2)+(2*6)+(1*9)=123
123 % 10 = 3
So 81262-69-3 is a valid CAS Registry Number.

81262-69-3Synthetic route

1--1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethane
81279-27-8

1--1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethane

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;
5-(chloromethyl)-1,3-benzodioxole
20850-43-5

5-(chloromethyl)-1,3-benzodioxole

sodium-compound of O-methyl-triethylene glycol

sodium-compound of O-methyl-triethylene glycol

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) LDA, hexamethylphosphoramide / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT, overnight
2: triethylamine / H2O; acetone / 0 °C
3: NaN3 / H2O; acetone / 0.75 h / Ambient temperature
4: toluene / 0.5 h / Heating
5: Heating
6: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme
5-(2-Isocyanato-2-methyl-propyl)-benzo[1,3]dioxole

5-(2-Isocyanato-2-methyl-propyl)-benzo[1,3]dioxole

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Heating
2: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme
2,2-dimethyl-3-<3,4-(methylenedioxy)phenyl>propionic acid
54508-53-1

2,2-dimethyl-3-<3,4-(methylenedioxy)phenyl>propionic acid

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / H2O; acetone / 0 °C
2: NaN3 / H2O; acetone / 0.75 h / Ambient temperature
3: toluene / 0.5 h / Heating
4: Heating
5: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme
3-Benzo[1,3]dioxol-5-yl-2,2-dimethyl-propionyl azide

3-Benzo[1,3]dioxol-5-yl-2,2-dimethyl-propionyl azide

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / 0.5 h / Heating
2: Heating
3: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme
C15H18O6

C15H18O6

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine
81262-69-3

N-methyl-1,1-dimethyl-2-<3,4-(methylenedioxy)phenyl>ethylamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaN3 / H2O; acetone / 0.75 h / Ambient temperature
2: toluene / 0.5 h / Heating
3: Heating
4: LiAlH4 / tetrahydrofuran / 24 h / Heating
View Scheme

81262-69-3Downstream Products

81262-69-3Relevant academic research and scientific papers

Effects of Certain Hallucinogenic Amphetamine Analogues on the Release of Serotonin from Rat Brain Synaptosomes

Nichols, David E.,Lloyd, David H.,Hoffman, Andrew J.,Nichols, Maxine B.,Yim, George K. W.

, p. 530 - 535 (2007/10/02)

The enantiomers of 3,4-(methylenedioxy)amphetamine (MDA), p-methoxyamphetamine (PMA), and N-Me-MDA (MDMA), along with their α,α-dimethylated derivatives, were evaluated for an effect on the release of serotonin from rat whole brain synaptosomes.The amphetamine isomers were all potent in inducing the release of serotonin at bath concentrations of 1 and 10 μM but were inactive at 0.1 μM.No significant difference in isomer potency was observed at the 10-μM concentration.However, at 1 μM the (+) isomer of MDMA was more effective in inducing release than was the (-) isomer.Since it is the (+) isomer which is clinically active, this result suggests that transmitter release may play a role in the biological activity of MDMA.By contrast, the α,α-dimethyl compounds were not effective in releasing serotonin, even at the highest bath concentration.

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