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MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA.[1][2][3][4][5] It is known by the nicknames “Eden” and “Methyl-J“.[5]
Use and effects
MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story.[1] MBDB’s dose, according to PiHKAL, is 180 to 210 mg; the proper dosage relative to body mass seems unknown.[1][2] Its duration is 4 to 8 hours, with noticeable after-effects lasting for 1 to 3 hours.[1][2]
MBDB was initially developed as a non-psychedelic entactogen. It has lower effects on the dopamine system in comparison to other entactogens such as MDMA. MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers and inhibitions, pronounced sense of empathy and compassion, and mild euphoria, all of which are present.[1] MBDB tends to produce less euphoria, psychedelia, and stimulation in comparison to MDMA.[1]
Clinical studies have found that MBDB produces similar entactogenic effects to MDMA, but lacks psychedelic and stimulant effects.[2][3] It enhances mood similarly to MDMA, but lacks the pronounced euphoria of MDMA.[2] MBDB produces prosocial effects similarly to MDMA, although it is said to be moderately less effective.[2]
Interactions
Pharmacology
Pharmacodynamics
MBDB acts as a serotonin–norepinephrine releasing agent (SNRA).[2][3][6] Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 540 nM for serotonin, 3,300 nM for norepinephrine (6.1-fold lower than for serotonin), and >100,000 for dopamine (>185-fold lower than for serotonin).[6] However, it may still have slight dopamine-releasing actions.[3] MBDB fully substitutes for MDMA in drug discrimination tests in rodents.[2][3] It increases locomotor activity similarly to but less robustly than MDMA.[7] Likewise, MBDB increases conditioned place preference (CPP) similarly but less efficaciously than MDMA.[3] In contrast to MDMA, which produced hyperthermia, MBDB instead produced dose- and time-dependent hypothermia
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, commonly referred to as N-Methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine or MBDB, is a synthetic compound related to the family of substituted amphetamines. It is structurally similar to other psychoactive substances such as 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA), and has been studied for its potential stimulant and entactogenic properties. The compound is often associated with recreational drug use and has been subject to forensic analysis due to its presence in illicit drug markets.
The compound was first synthesized in the late 1990s and has since been reported in various scientific studies focusing on its synthesis, pharmacological effects, and potential risks. Its synthesis has been optimized for both laboratory research and potential medical applications, particularly in neuropharmacology.
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine is classified as a psychoactive substance within the broader category of phenethylamines. It is also categorized as a member of the entactogen class of drugs, which are known for their empathogenic effects.
Methods
The synthesis of N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine typically involves several key steps. One common method includes the methylation of 1-(1,3-benzodioxol-5-yl)-2-butanamine using methyl iodide or another methylating agent.
Technical Details
In one study, the radiosynthesis of N-[11C]methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine was achieved by methylation of its demethyl precursor at optimized conditions: a temperature of 130 °C for 8 minutes yielded an impressive radiochemical yield of 84% . The process was refined further to improve yields and reduce reaction times, demonstrating the compound’s adaptability for research purposes.
Structure
The molecular formula for N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine is C12H17NO2, with a molecular weight of approximately 207.27 g/mol. The compound features a benzodioxole moiety that contributes to its psychoactive properties.
Data
The InChIKey for this compound is USWVWJSAJAEEHQ-UHFFFAOYSA-N, and it has a CAS Registry Number of 135795-90-3. The structural representation includes a central butanamine chain with a methyl group attached to the nitrogen atom and a methylenedioxyphenyl group.
Reactions
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine undergoes various chemical reactions typical of amines and substituted phenols. These reactions can include oxidation, reduction, and substitution processes.
Technical Details
Forensic analyses have indicated that upon degradation or metabolic processes in biological systems, MBDB can produce several metabolites that may be detected in urine or blood samples. High-performance liquid chromatography (HPLC) techniques have been employed to separate and identify these metabolites effectively .
Process
The mechanism of action for N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine is believed to involve the modulation of neurotransmitter systems, particularly serotonin receptors. Research indicates that compounds like MBDB exhibit stimulant properties similar to MDMA but with distinct pharmacological profiles.
Data
Studies have shown that MBDB can produce significant behavioral effects in animal models, suggesting that its primary action may be through serotonergic pathways rather than dopaminergic ones . This serotonergic activity aligns with its classification as an entactogen.
Physical Properties
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine is typically presented as a white crystalline solid at room temperature. Its melting point and solubility characteristics vary based on purity and formulation.
Chemical Properties
The compound exhibits basic amine characteristics due to the presence of the nitrogen atom in its structure. It is susceptible to oxidation and other chemical modifications typical of phenolic compounds .
Relevant data include:
- Molecular Weight: 207.27 g/mol
- Boiling Point: Not extensively documented but expected to be higher than typical amines.
Scientific Uses
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine has potential applications in scientific research related to psychopharmacology and neurobiology. Its structural similarities to MDMA make it a candidate for studies investigating the mechanisms underlying mood enhancement and emotional processing.
Additionally, due to its psychoactive properties, it has been analyzed in forensic contexts to understand drug trends and patterns within illicit markets .
Molecular Structure and IUPAC Nomenclature of MBDB
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, systematically named according to IUPAC conventions as 1-(1,3-benzodioxol-5-yl)-N-methylbutan-2-amine, represents a ring-substituted phenethylamine derivative. The molecular formula is C₁₂H₁₇NO₂, with a molecular weight of 207.27 g/mol [1] [2] [6]. The core structure consists of a benzodioxole ring (3,4-methylenedioxyphenyl group) linked to a butanamine chain featuring a methyl group on the nitrogen atom. The critical distinction from MDMA lies in the alpha-carbon substitution, where MBDB carries an ethyl group (–CH₂CH₃) instead of MDMA’s methyl group (–CH₃) [6] [9]. This structural modification confers unique physicochemical and pharmacological properties.
The compound is registered under CAS number 135795-90-3 (racemic mixture) and is commonly abbreviated as MBDB, with additional synonyms including Methyl-J, Eden, and 3,4-methylenedioxy-N-methyl-α-ethylphenethylamine [2] [6]. Its planar structure is defined by the following key identifiers:
- InChI: InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3
- InChIKey: USWVWJSAJAEEHQ-UHFFFAOYSA-N [2]
Table 1: Molecular Identifiers of MBDB
| Property | Value |
|---|---|
| IUPAC Name | 1-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine |
| CAS Number (Racemate) | 135795-90-3 |
| Molecular Formula | C₁₂H₁₇NO₂ |
| Molecular Weight | 207.27 g/mol |
| Common Abbreviations | MBDB, Methyl-J, Eden |
Physicochemical Properties: Thermodynamic and Kinetic Parameters
MBDB exists as a solid at room temperature with a melting point of 156°C [6]. Thermodynamic analyses reveal a calculated Gibbs free energy of formation (ΔfG°) of 126.48 kJ/mol and an enthalpy of formation (ΔfH°gas) of -200.09 kJ/mol [7]. The compound exhibits moderate lipophilicity, with an octanol-water partition coefficient (logP) of 1.956, indicating greater hydrophobicity than MDMA (logP ≈ 1.58) [6] [7]. This property influences its blood-brain barrier permeability and distribution kinetics.
Vapor pressure analysis shows a critical temperature (Tc) of 843.18 K and critical pressure (Pc) of 2761.36 kPa [7]. The McGowan molar volume (McVol) is 167.040 ml/mol, while the boiling point (Tboil) is calculated at 625.64 K [7]. Kinetic solubility studies indicate limited aqueous solubility, consistent with its log value of water solubility (log10WS) of -3.04 [7]. These parameters collectively suggest MBDB favors organic solvents, aligning with typical extraction and analytical practices for phenylalkylamine derivatives.
Table 2: Thermodynamic and Physical Properties of MBDB
| Property | Value | Unit |
|---|---|---|
| Melting Point | 156 | °C |
| ΔfG° | 126.48 | kJ/mol |
| ΔfH°gas | -200.09 | kJ/mol |
| logP (Octanol-Water) | 1.956 | – |
| Boiling Point (Tboil) | 625.64 | K |
| Critical Temperature (Tc) | 843.18 | K |
| Critical Pressure (Pc) | 2761.36 | kPa |
| Molar Volume (McVol) | 167.040 | ml/mol |
Stereochemical Considerations: Enantiomeric Forms and Their Synthesis
MBDB contains a chiral center at the alpha carbon of the butanamine chain, giving rise to two enantiomers: (R)-MBDB and (S)-MBDB. The (R)-enantiomer is designated under CAS 54585856 [4]. Stereoselective synthesis typically employs reductive amination of 1-(1,3-benzodioxol-5-yl)butan-2-one using methylamine and a chiral catalyst, though specific yields and optical purity data remain limited in open literature [6] [8].
Radiolabeled synthesis for research purposes has been achieved via N-[¹¹C]methylation of the desmethyl precursor 1-(1,3-benzodioxol-5-yl)butan-2-amine (BDB). Optimal conditions (130°C, 8 min, 3 mg precursor) yield 84% radiochemical purity with specific activity reaching 300 GBq/μmol [8]. Pharmacological studies in rodents reveal minimal behavioral differences between enantiomers, contrasting sharply with the marked stereoselectivity observed in MDMA’s effects [5] [6]. Specifically, drug discrimination tests show complete substitution of racemic MBDB for both (R)- and (S)-enantiomers, indicating similar receptor interaction profiles [6].
Comparative Structural Analysis with MDMA and Related Entactogens
Structurally, MBDB is the α-ethyl homologue of MDMA, sharing the 3,4-methylenedioxy-substituted phenyl ring but differing in alkyl chain length [3] [9]. This modification reduces dopamine transporter (DAT) affinity and dopaminergic activity while preserving serotonin transporter (SERT) interactions. Quantitative neurochemical profiling shows MBDB’s potency in serotonin release (EC₅₀ = 540 nM) is comparable to MDMA, but its norepinephrine release (EC₅₀ = 3,300 nM) is 6.1-fold weaker and dopamine release (>100,000 nM) is >185-fold weaker than its serotonergic effects [6]. This explains MBDB’s reduced stimulant and euphoriant properties relative to MDMA [3] [9].
Rigid analogs like 5,6-methylenedioxy-2-aminoindan (MDAI) retain entactogen-like discriminative stimulus properties despite lacking neurotoxic potential, demonstrating structural flexibility within this class [5]. The benzodioxole ring’s planarity is conserved across MDMA, MBDB, and MDAI, but the α-alkyl chain length critically modulates pharmacological selectivity. Shorter chains (e.g., MDMA’s α-methyl) enhance dopamine release and stimulant effects, while longer chains (e.g., MBDB’s α-ethyl) favor serotonergic specificity [3] [5] [6].
Table 3: Structural and Neuropharmacological Comparison of MBDB and MDMA
| Property | MBDB | MDMA |
|---|---|---|
| Core Structure | α-Ethyl homologue | α-Methyl homologue |
| Dopamine Release (EC₅₀) | >100,000 nM | ~500 nM |
| Serotonin Release (EC₅₀) | 540 nM | ~100 nM |
| SERT Affinity | High | High |
| DAT Affinity | Negligible | Moderate |
| 5-HT₂A Receptor Efficacy | Low (No head-twitch response) | Moderate |
| Neurotoxicity Mechanism | Selective serotonergic deficits | Mixed serotonergic/dopaminergic deficits |
Properties
CAS Number
Product Name
IUPAC Name
Molecular Formula
Molecular Weight
InChI
InChI Key
SMILES
Synonyms
N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (R)-isomer
N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (S)-isome
Canonical SMILES
1,3-Benzodioxolyl-N-methylbutanamine
1,3-Benzodioxolyl-N-methylbutanamine structure
|
Common Name | 1,3-Benzodioxolyl-N-methylbutanamine | ||
|---|---|---|---|---|
| CAS Number | 103818-46-8 | Molecular Weight | 207.269 | |
| Density | 1.1±0.1 g/cm3 | Boiling Point | 299.8±9.0 °C at 760 mmHg | |
| Molecular Formula | C12H17NO2 | Melting Point | N/A | |
| MSDS | N/A | Flash Point | 122.1±8.2 °C | |
| Purity | Quantity | Budget | Inquiry |
|---|
| Name | 1-(1,3-benzodioxol-5-yl)-N-methylbutan-2-amine |
|---|---|
| Synonym | More Synonyms |
| Density | 1.1±0.1 g/cm3 |
|---|---|
| Boiling Point | 299.8±9.0 °C at 760 mmHg |
| Molecular Formula | C12H17NO2 |
| Molecular Weight | 207.269 |
| Flash Point | 122.1±8.2 °C |
| Exact Mass | 207.125931 |
| PSA | 30.49000 |
| LogP | 2.34 |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.531 |
| N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine |
| MBDB |
| UNII:E8HMQ4F9JQ |
| 1-(1,3-Benzodioxol-5-yl)-N-methyl-2-butanamine |
| 1-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine |
| 1,3-Benzodioxolyl-N-methylbutanamine |
| Methylbenzodioxolylbutanamine |
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MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA.[1][2][3][4][5] It is known by the nicknames “Eden” and “Methyl-J“.[5]
Use and effects
MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story.[1] MBDB’s dose, according to PiHKAL, is 180 to 210 mg; the proper dosage relative to body mass seems unknown.[1][2] Its duration is 4 to 8 hours, with noticeable after-effects lasting for 1 to 3 hours.[1][2]
MBDB was initially developed as a non-psychedelic entactogen. It has lower effects on the dopamine system in comparison to other entactogens such as MDMA. MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers and inhibitions, pronounced sense of empathy and compassion, and mild euphoria, all of which are present.[1] MBDB tends to produce less euphoria, psychedelia, and stimulation in comparison to MDMA.[1]
Clinical studies have found that MBDB produces similar entactogenic effects to MDMA, but lacks psychedelic and stimulant effects.[2][3] It enhances mood similarly to MDMA, but lacks the pronounced euphoria of MDMA.[2] MBDB produces prosocial effects similarly to MDMA, although it is said to be moderately less effective.
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Interactions
Pharmacology
Pharmacodynamics
MBDB acts as a serotonin–norepinephrine releasing agent (SNRA).[2][3][6] Its EC50Tooltip half-maximal effective concentration values for induction of monoamine release are 540 nM for serotonin, 3,300 nM for norepinephrine (6.1-fold lower than for serotonin), and >100,000 for dopamine (>185-fold lower than for serotonin).[6] However, it may still have slight dopamine-releasing actions.[3] MBDB fully substitutes for MDMA in drug discrimination tests in rodents.[2][3] It increases locomotor activity similarly to but less robustly than MDMA.[7] Likewise, MBDB increases conditioned place preference (CPP) similarly but less efficaciously than MDMA.[3] In contrast to MDMA, which produced hyperthermia, MBDB instead produced dose- and time-dependent hypothermia.[7]
MBDB has similar affinities for the serotonin 5-HT1A and 5-HT2A receptors as MDMA.[2][8] However, MBDB did not show the head-twitch response, a behavioral proxy of psychedelic effects, at any dose in rodents.[7] In addition, MBDB (as well as MDMA) do not substitute for lysergic acid diethylamide (LSD) in drug discrimination tests.[3] The lack of apparent hallucinogenic effects with MBDB is analogous to the case of Ariadne, the α-ethyl homologue of DOM; (R)-Ariadne (BL-3912A) showed no psychedelic effects in humans at doses of up to 270 mg orally, whereas DOM is active as a hallucinogen at doses of 5 to 10 mg orally.[8][9] This may be due to lower activational efficacy at the serotonin 5-HT2A receptor.[9]
MBDB is a serotonergic neurotoxin similarly to MDMA.[2][3][10] However, MBDB appears to have reduced serotonergic neurotoxicity compared to MDMA at behaviorally equivalent doses.[2][3][10][4] In addition, unlike MDMA, MBDB does not produce dopaminergic neurotoxicity in mice.[10]
MBDB and its individual enantiomers, (S)-MBDB and (R)-MBDB, show similar behavioral effects in animals.[7]
Pharmacokinetics
The metabolism of MBDB has been described in the scientific literature.[11]
Chemistry
MBDB is a ring substituted amphetamine and an analogue of MDMA. Like MDMA, it has a methylenedioxy substitution at the 3 and 4 position on the aromatic ring; this is perhaps the most distinctive feature that structurally define analogues of MDMA, in addition to their unique effects, and as a class they are often referred to as “entactogens” to differentiate between typical stimulant amphetamines that (as a general rule) are not ring substituted.[citation needed] MBDB differs from MDMA by having an ethyl group instead of a methyl group attached to the alpha carbon. Modification at the alpha carbon is uncommon for substituted amphetamines.[citation needed]
Analogues
Analogues of MBDB (methyl-J) include BDB (J), EBDB (ethyl-J), BDP (K), MBDP (methyl-K), EBDP (ethyl-K), MPAP (PBDP; propyl-K), and UWA-101 (α-cyclopropyl-MDPEA), among others.[1]
History
MBDB was first described in the scientific literature by a group that included David E. Nichols, Robert A. Oberlender, Peyton Jacob III, and Alexander Shulgin in 1986.[12][13]
Society and culture
Legal status
International
Unlike MDMA, MBDB is not internationally scheduled under the United Nations Convention on Psychotropic Substances. The thirty-second meeting of the WHO Expert Committee on Drug Dependence (September 2000) evaluated MBDB and recommended against scheduling.[14] From the WHO Expert Committee assessment of MBDB:
- Although MBDB is both structurally and pharmacologically similar to MDMA, the limited available data indicate that its stimulant and euphoriant effects are less pronounced than those of MDMA. There have been no reports of adverse or toxic effects of MBDB in humans. Law enforcement data on illicit trafficking of MBDB in Europe suggest that its availability and abuse may now be declining after reaching a peak during the latter half of the 1990s. For these reasons, the Committee did not consider the abuse liability of MBDB would constitute a significant risk to public health, thereby warranting its placement under international control. Scheduling of MBDB was therefore not recommended.
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N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine Class Small Molecule Description 1,3-Benzodioxolyl-N-methylbutanamine (N-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names Eden and Methyl-J. MBDB is a closely related chemical analogue of MDMA, with the only difference between the two molecules being an ethyl group instead of a methyl group attached to the alpha carbon. It has IC50 values of 784 nM against 5-HT, 7825 nM against dopamine, and 1233 nM against norepinephrine. Its metabolism has been described in scientific literature.MBDB was first synthesized by pharmacologist and medicinal chemist David E. Nichols and later tested by Alexander Shulgin and described in his book, PiHKAL: A Chemical Love Story. MBDB’s dosage, according to PiHKAL, is 180–210 mg; the proper dosage relative to body mass seems unknown. Its duration is 4–6 hours, with noticeable after-effects lasting for 1–3 hours. MBDB was initially developed as a non-psychedelic entactogen. It has lower effects on the dopamine system in comparison to other entactogens such as MDMA. MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers and inhibitions, pronounced sense of empathy and compassion, mood lift, and mild euphoria, all of which are present. MBDB tends to produce less euphoria, psychedelia, and stimulation in comparison to MDMA. Contaminant Sources - STOFF IDENT Compounds
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Chemical Structure 
Synonyms Value Source N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (S)-isomer MeSH N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine MeSH N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine, (R)-isomer MeSH Chemical Formula C12H17NO2 Average Molecular Mass 207.273 g/mol Monoisotopic Mass 207.126 g/mol CAS Registry Number 135795-90-3 IUPAC Name [1-(2H-1,3-benzodioxol-5-yl)butan-2-yl](methyl)amine Traditional Name methylbenzodioxolylbutanamine SMILES CCC(CC1=CC2=C(OCO2)C=C1)NC InChI Identifier InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3 InChI Key USWVWJSAJAEEHQ-UHFFFAOYSA-N Chemical Taxonomy Description belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Kingdom Organic compounds Super Class Organoheterocyclic compounds Class Benzodioxoles Sub Class Not Available Direct Parent Benzodioxoles Alternative Parents Substituents - Benzodioxole
- Aralkylamine
- Benzenoid
- Oxacycle
- Secondary amine
- Secondary aliphatic amine
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Amine
- Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
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MBDB (hydrochloride) (N-Methyl-1,3-Benzodioxolylbutanamine, CAS …
MBDB is an analog of methylenedioxymethamphetamine (MDMA), differing only by the substitution of an ethyl for methyl group at the …
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MBDB, also known as N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an …
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1,3-Benzodioxolyl-N-methylbutanamine | CAS#:103818-46-8 | Chemsrc
Aug 14, 2026 · Chemsrc provides 1,3-Benzodioxolyl-N-methylbutanamine (CAS#:103818-46-8) MSDS, density, melting point, boiling …
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Buy N-Methyl-1- (1,3-benzodioxol-5-yl)-2-butanamine (EVT-1216877 …
N-Methyl-1- (1,3-benzodioxol-5-yl)-2-butanamine has potential applications in scientific research related to psychopharmacology and …
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