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Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Phase II Reactions: Methylation Reactions01:17

Phase II Reactions: Methylation Reactions

Methylation is a phase II biotransformation process involving the attachment of a methyl group to a substrate. Enzymes known as methyltransferases orchestrate this reaction.
The mechanism of methylation unfolds in two stages. The first stage sees a methyltransferase enzyme facilitating the transfer of a methyl group from S-adenosylmethionine (SAM) to the substrate, forming S-adenosylhomocysteine (SAH). The second stage involves further metabolism of SAH into homocysteine, which can be recycled...
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
Sedatives and Hypnotics Drugs: Benzodiazepines01:19

Sedatives and Hypnotics Drugs: Benzodiazepines

Benzodiazepines have both sedative and hypnotic properties. They include compounds such as diazepam (Valium) and alprazolam (Xanax). Structurally, their cores are similar, consisting of the fusion of a benzene ring and a diazepine ring, but they share a common mechanism of action in the central nervous system (CNS).
Benzodiazepines work by enhancing the effects of the inhibitory neurotransmitter GABA. They bind to the GABAA receptor, increasing its affinity for GABA, which opens chloride...
Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
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Related Experiment Video

Updated: Jun 12, 2026

Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
07:06

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Published on: November 15, 2017

N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB): its properties and possible risks.

L A Aerts1, M Mallaret, H Rigter

  • 1Trimbos Institute, Netherlands Institute of Mental Health and Addiction, Utrecht, The Netherlands.

Addiction Biology
|June 26, 2010
PubMed
Summary

N-methyl-1-(1,3-benzodioxol-5-yl)-2-aminobutane (MBDB) is an entactogen with effects similar to MDMA but less potent and with a lower risk of neurotoxicity. MBDB shows a smaller margin of safety than MDMA, indicating a non-negligible risk of neurotoxicity.

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Last Updated: Jun 12, 2026

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Published on: November 15, 2017

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09:54

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Published on: August 20, 2018

Area of Science:

  • Pharmacology
  • Neuroscience
  • Toxicology

Background:

  • MBDB (N-methyl-1-(1,3-benzodioxol-5-yl)-2-aminobutane) is the alpha-ethyl homologue of MDMA (3,4-methylenedioxy-N-methylamphetamine).
  • MBDB is metabolized and excreted similarly to MDMA, with the majority likely excreted unmetabolized in urine.

Purpose of the Study:

  • To compare the neuropharmacological, neuroendocrine, and neurophysiological effects of MBDB with MDMA.
  • To assess the toxicological profile and dependence potential of MBDB.

Main Methods:

  • Neuropharmacological studies in rats (serotonin and dopamine release, re-uptake inhibition).
  • Neuroendocrine assessments (plasma ACTH, corticosterone, prolactin, renin).
  • Neurophysiological recordings (EEG frequency bands).
  • Drug discrimination tests, locomotor activity, and conditioned place preference tests in rats.
  • Calculation of margin of safety for neurotoxicity.

Main Results:

  • MBDB increases serotonin release and inhibits serotonin and noradrenaline re-uptake, similar to MDMA but less potent.
  • MBDB shows less dopamine release and re-uptake inhibition compared to MDMA.
  • Neuroendocrine effects of MBDB resemble MDMA, increasing ACTH, corticosterone, prolactin, and renin.
  • MBDB decreases overall brain electrical activity, unlike hallucinogens.
  • MBDB has weaker rewarding properties than MDMA and a smaller dependence potential.
  • MBDB is three times less likely to cause serotonergic brain deficits than MDMA, but the margin of safety is less than one for both.

Conclusions:

  • MBDB is an entactogen with pharmacological and neuroendocrine effects similar to MDMA but generally less potent.
  • MBDB exhibits a lower risk of neurotoxicity and dependence potential compared to MDMA.
  • Despite a lower risk, the margin of safety for MBDB is less than one, indicating a non-negligible risk of neurotoxicity.