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| Other names | Methylbenzodioxolyl-butanamine;N-Methyl-1,3-benzodioxolylbutanamine; MBDB; 3,4-Methylenedioxy-N-methyl-butanphenamine; MDMB; 1,3-Benzodioxolyl-N-methylbutanamine; BDMB; 3,4-Methylenedioxy-N-methyl-α-ethylphenylethylamine; 3,4-Methylenedioxy-N-methyl-α-desmethyl-α-ethylamphetamine; Eden; Methyl-J |
| Drug class | Serotonin–norepinephrine releasing agent;Empathogen–entactogen |
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| Duration of action | 4–6 hours |
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| Chemical and physical data | |
| Formula | C12H17NO2 |
| Molar mass | 207.273 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 156 °C (313 °F) |
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MBDB, also known asN-methyl-1,3-benzodioxolylbutanamine or as3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is anentactogen of thephenethylamine,amphetamine, andphenylisobutylamine families related toMDMA.[1][2][3][4] It is known by the street names "Eden" and "Methyl-J".[4]
MBDB was firstsynthesized bypharmacologist andmedicinal chemistDavid E. Nichols[citation needed] and later tested byAlexander Shulgin and described in his book,PiHKAL: A Chemical Love Story. MBDB's dosage, according toPiHKAL, is 180 to 210 mg; the proper dosage relative to body mass seems unknown.[1] Its duration is 4 to 6 hours, with noticeable after-effects lasting for 1 to 3 hours.[1][additional citation(s) needed]
MBDB was initially developed as a non-psychedelic entactogen. It has lower effects on thedopamine system in comparison to other entactogens such asMDMA.[citation needed] MBDB causes many mild, MDMA-like effects, in particular the lowering of social barriers andinhibitions, pronounced sense ofempathy andcompassion, and mildeuphoria, all of which are present.[citation needed] MBDB tends to produce less euphoria,psychedelia, andstimulation in comparison to MDMA.[citation needed]
Clinical studies have found that MBDB produces similarentactogenic effects to MDMA, but lackspsychedelic andstimulant effects.[1][2] It enhancesmood similarly to MDMA, but lacks the pronouncedeuphoria of MDMA.[1] MBDB producesprosocial effects similarly to MDMA, although it is said to be moderately less effective.[1]
MBDB is a ring substituted amphetamine and ananalogue ofMDMA. 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 typicalstimulantamphetamines that (as a general rule) are not ring substituted. MBDB differs from MDMA by having anethyl group instead of amethyl group attached to thealpha carbon; all other parts are identical. Modification at the alpha carbon is uncommon for substituted amphetamines.
MBDB acts as aserotonin–norepinephrine releasing agent (SNRA).[1][2][5] ItsEC50Tooltip half-maximal effective concentration values forinduction of monoamine release are 540 nM forserotonin, 3,300 nM fornorepinephrine (6.1-fold lower than for serotonin), and >100,000 fordopamine (>185-fold lower than for serotonin).[5] However, it may still have slight dopamine-releasing actions.[2] MBDB fully substitutes forMDMA indrug discrimination tests in rodents.[1][2] It increaseslocomotor activity similarly to but less robustly thanMDMA.[6] Likewise, MBDB increasesconditioned place preference (CPP) similarly but less efficaciously than MDMA.[2] In contrast to MDMA, which producedhyperthermia, MBDB instead produced dose- and time-dependenthypothermia.[6]
MBDB has similaraffinities for theserotonin5-HT1A and5-HT2A receptors as MDMA.[1][7] However, MBDB did not show thehead-twitch response, a behavioral proxy ofpsychedelic effects, at any dose in rodents.[6] In addition, MBDB (as well as MDMA) do not substitute forlysergic acid diethylamide (LSD) indrug discrimination tests.[2] The lack of apparent hallucinogenic effects with MBDB is analogous to the case ofAriadne, the α-ethyl homologue ofDOM; (R)-Ariadne (BL-3912A) showed no psychedelic effects in humans at doses of up to 270 mgorally, whereas DOM is active as a hallucinogen at doses of 5 to 10 mg orally.[7][8] This may be due to lower activationalefficacy at the serotonin 5-HT2A receptor.[8]
MBDB is aserotonergic neurotoxin similarly to MDMA.[1][2][9] However, MBDB appears to have reduced serotonergic neurotoxicity compared to MDMA at behaviorally equivalent doses.[1][2][9][3] In addition, unlike MDMA, MBDB does not producedopaminergic neurotoxicity in mice.[9]
MBDB and its individualenantiomers, (S)-MBDB and (R)-MBDB, show similar behavioral effects in animals.[6]
Themetabolism of MBDB has been described in thescientific literature.[10]
Unlike MDMA, MBDB is not internationally scheduled under the United NationsConvention on Psychotropic Substances. The thirty-second meeting of the WHO Expert Committee on Drug Dependence (September 2000) evaluated MBDB and recommended against scheduling.[11] From the WHO Expert Committee assessment of MBDB:
MBDB is considered a Schedule 9 Prohibited substance in Australia under thePoisons Standard (October 2015).[12] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[12]
Scheduled in the "government decree on psychoactive substances banned from the consumer market".[13]
MBDB is included into Schedule 1 of the Controlled Substances Act.[14]
Sveriges riksdags health ministryStatens folkhälsoinstitut [sv] classified MBDB as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor [sv] (translatedAct on the Prohibition of Certain Goods Dangerous to Health) as of Feb 25, 1999, in their regulation SFS 1999:58 listed as "2-metylamino-1-(3,4-metylendioxifenyl)-butan (MBDB)", making it illegal to sell or possess.[15]
MBDB is being assessed by PharmAla Biotech for potential medical use as apharmaceutical drug, for instance to treatautism.[7][16][17][6]
Author Disclosure Statement: H.K. is Vice President of Research at PharmAla Biotech and is listed as an inventor on patents related to the research in this review article. H.E.S. receives salary supported from a contract between PharmAla Biotech and UAMS. W.E.F. receives research funds and salary support from a contract between PharmAla Biotech and UAMS. The other authors have no conflicts to disclose.
