View source for MBDB

{{Short description|Chemical compound}}
{{Infobox drug
| verifiedrevid = 447191426
| drug_name = Methylbenzodioxolylbutanamine
| image = MBDB.svg
| width = 
| image2 = MBDB-3d-sticks.png
| width2 = 
| caption = Chemical structure

<!--Clinical data-->
| tradename = 
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category = 
| routes_of_administration = 
| class = [[Serotonin–norepinephrine releasing agent]]; [[Empathogen–entactogen]]

<!--Legal status -->
| legal_AU = S9
| legal_CA = 
| legal_US = [[Controlled Substances Act#Schedule I controlled substances|Schedule I]] (Positional Isomer of [[3,4-Methylenedioxy-N-ethylamphetamine|MDEA]])
| legal_UK = Class A
| legal_DE = Anlage I

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| duration_of_action = 4–6 hours
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 135795-90-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E8HMQ4F9JQ
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 124844
| KEGG = C22786
| ChemSpiderID = 111153
| synonyms = 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

<!--Chemical data-->
| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)-''N''-methylbutan-2-amine
| C = 12 | H = 17 | N = 1 | O = 2
| SMILES = CCC(CC1=CC2=C(C=C1)OCO2)NC
| StdInChI = 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
| StdInChIKey = USWVWJSAJAEEHQ-UHFFFAOYSA-N

<!--Physical data -->
| melting_point = 156
}}

'''MBDB''', also known as '''''N''-methyl-1,3-benzodioxolylbutanamine''' or as '''3,4-methylenedioxy-''N''-methyl-α-ethylphenylethylamine''', is an [[entactogen]] of the [[substituted phenethylamine|phenethylamine]], [[substituted amphetamine|amphetamine]], and [[phenylisobutylamine]] families related to [[MDMA]].<ref name="Oeri2021">{{cite journal | vauthors = Oeri HE | title = Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy | journal = J Psychopharmacol | volume = 35 | issue = 5 | pages = 512–536 | date = May 2021 | pmid = 32909493 | pmc = 8155739 | doi = 10.1177/0269881120920420 | url = }}</ref><ref name="AertsMallaretRigter2000">{{cite journal | vauthors = Aerts LA, Mallaret M, Rigter H | title = N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB): its properties and possible risks | journal = Addict Biol | volume = 5 | issue = 3 | pages = 269–282 | date = July 2000 | pmid = 20575841 | doi = 10.1111/j.1369-1600.2000.tb00191.x | url = }}</ref><ref name="NicholsMarona-LewickaHuang1993" /><ref name="Erowid-MBDB">{{cite web|url=https://www.erowid.org/chemicals/mbdb/|title=MBDB | work = Erowid Center }}</ref> It is known by the street names "'''Eden'''" and "'''Methyl-J'''".<ref name="Erowid-MBDB" />

==History and effects==
{{More citations needed section|date=May 2025}}
MBDB was first [[chemical synthesis|synthesized]] by [[pharmacologist]] and [[medicinal chemist]] [[David E. Nichols]] and later tested by [[Alexander Shulgin]] and described in his book, ''[[PiHKAL|PiHKAL: A Chemical Love Story]]''. MBDB's dosage, according to ''PiHKAL'', is 180 to 210{{nbsp}}mg; the proper dosage relative to body mass seems unknown.<ref name="Oeri2021" /> Its duration is 4 to 6{{nbsp}}hours, with noticeable after-effects lasting for 1 to 3{{nbsp}}hours.<ref name="Oeri2021" />

MBDB was initially developed as a non-[[psychedelic drug|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 [[social inhibition|inhibitions]], pronounced sense of [[empathy]] and [[compassion]], and mild [[euphoria]], all of which are present. MBDB tends to produce less euphoria, [[psychedelic experience|psychedelia]], and [[stimulant|stimulation]] in comparison to MDMA.

Clinical studies have found that MBDB produces similar [[entactogen]]ic effects to MDMA, but lacks [[psychedelic drug|psychedelic]] and [[stimulant]] effects.<ref name="Oeri2021" /><ref name="AertsMallaretRigter2000" /> It enhances [[mood (psychology)|mood]] similarly to MDMA, but lacks the pronounced [[euphoria]] of MDMA.<ref name="Oeri2021" /> MBDB produces [[prosocial]] effects similarly to MDMA, although it is said to be moderately less effective.<ref name="Oeri2021" />

==Chemistry==
MBDB is a ring substituted amphetamine and an [[Structural analog|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|date=June 2025}} 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|date=June 2025}}

==Pharmacology==
===Pharmacodynamics===
MBDB acts as a [[serotonin–norepinephrine releasing agent]] (SNRA).<ref name="Oeri2021" /><ref name="AertsMallaretRigter2000" /><ref name="NagaiNonakaSatohHisashiKamimura2007">{{cite journal | vauthors = Nagai F, Nonaka R, Satoh Hisashi Kamimura K | title = The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | journal = Eur J Pharmacol | volume = 559 | issue = 2–3 | pages = 132–137 | date = March 2007 | pmid = 17223101 | doi = 10.1016/j.ejphar.2006.11.075 | url = }}</ref> Its {{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}} values for [[monoamine releasing agent|induction of monoamine release]] are 540{{nbsp}}nM for [[serotonin]], 3,300{{nbsp}}nM for [[norepinephrine]] (6.1-fold lower than for serotonin), and >100,000 for [[dopamine]] (>185-fold lower than for serotonin).<ref name="NagaiNonakaSatohHisashiKamimura2007" /> However, it may still have slight dopamine-releasing actions.<ref name="AertsMallaretRigter2000" /> MBDB fully substitutes for [[MDMA]] in [[drug discrimination]] tests in rodents.<ref name="Oeri2021" /><ref name="AertsMallaretRigter2000" /> It increases [[locomotor activity]] similarly to but less robustly than [[MDMA]].<ref name="CarkShawFantegrossi2024" /> Likewise, MBDB increases [[conditioned place preference]] (CPP) similarly but less efficaciously than MDMA.<ref name="AertsMallaretRigter2000" /> In contrast to MDMA, which produced [[hyperthermia]], MBDB instead produced dose- and time-dependent [[hypothermia]].<ref name="CarkShawFantegrossi2024" />

MBDB has similar [[affinity (pharmacology)|affinities]] for the [[serotonin]] [[5-HT1A receptor|5-HT<sub>1A</sub>]] and [[5-HT2A receptor|5-HT<sub>2A</sub> receptor]]s as MDMA.<ref name="Oeri2021" /><ref name="KaurKarabulutGauld2023">{{cite journal | vauthors = Kaur H, Karabulut S, Gauld JW, Fagot SA, Holloway KN, Shaw HE, Fantegrossi WE | title = Balancing Therapeutic Efficacy and Safety of MDMA and Novel MDXX Analogues as Novel Treatments for Autism Spectrum Disorder | date = 2023 | journal = Psychedelic Medicine | volume = 1 | issue = 3 | pages = 166–185 | doi = 10.1089/psymed.2023.0023 | pmid = 40046567 | url = | quote = 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.| pmc = 11661495 }}</ref> However, MBDB did not show the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, at any dose in rodents.<ref name="CarkShawFantegrossi2024" /> In addition, MBDB (as well as MDMA) do not substitute for [[lysergic acid diethylamide]] (LSD) in [[drug discrimination]] tests.<ref name="AertsMallaretRigter2000" /> The lack of apparent hallucinogenic effects with MBDB is analogous to the case of [[Ariadne (drug)|Ariadne]], the α-ethyl homologue of [[DOM (drug)|DOM]]; (''R'')-Ariadne (BL-3912A) showed no psychedelic effects in humans at doses of up to 270{{nbsp}}mg [[oral administration|orally]], whereas DOM is active as a hallucinogen at doses of 5 to 10{{nbsp}}mg orally.<ref name="KaurKarabulutGauld2023" /><ref name="CunninghamBockSerrano2023">{{cite journal | vauthors = Cunningham MJ, Bock HA, Serrano IC, Bechand B, Vidyadhara DJ, Bonniwell EM, Lankri D, Duggan P, Nazarova AL, Cao AB, Calkins MM, Khirsariya P, Hwu C, Katritch V, Chandra SS, McCorvy JD, Sames D | title = Pharmacological Mechanism of the Non-hallucinogenic 5-HT<sub>2A</sub> Agonist Ariadne and Analogs | journal = ACS Chemical Neuroscience | volume = 14 | issue = 1 | pages = 119–135 | date = January 2023 | pmid = 36521179 | pmc = 10147382 | doi = 10.1021/acschemneuro.2c00597 }}</ref> This may be due to lower activational [[intrinsic activity|efficacy]] at the serotonin 5-HT<sub>2A</sub> receptor.<ref name="CunninghamBockSerrano2023" />

MBDB is a [[serotonergic neurotoxin]] similarly to MDMA.<ref name="Oeri2021" /><ref name="AertsMallaretRigter2000" /><ref name="JohnsonNichols1989">{{cite journal | vauthors = Johnson MP, Nichols DE | title = Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration | journal = Pharmacol Biochem Behav | volume = 33 | issue = 1 | pages = 105–108 | date = May 1989 | pmid = 2476831 | doi = 10.1016/0091-3057(89)90437-1 | url = }}</ref> However, MBDB appears to have reduced serotonergic neurotoxicity compared to MDMA at behaviorally equivalent doses.<ref name="Oeri2021" /><ref name="AertsMallaretRigter2000" /><ref name="JohnsonNichols1989" /><ref name="NicholsMarona-LewickaHuang1993">{{cite journal | vauthors = Nichols DE, Marona-Lewicka D, Huang X, Johnson MP | title = Novel serotonergic agents | journal = Drug des Discov | volume = 9 | issue = 3–4 | pages = 299–312 | date = 1993 | pmid = 8400010 | doi = | url = https://bitnest.netfirms.com/external/DrugDes.Disc/9.299 }}</ref> In addition, unlike MDMA, MBDB does not produce [[dopaminergic neurotoxin|dopaminergic neurotoxicity]] in mice.<ref name="JohnsonNichols1989" />

MBDB and its individual [[enantiomer]]s, (''S'')-MBDB and (''R'')-MBDB, show similar behavioral effects in animals.<ref name="CarkShawFantegrossi2024" />

===Pharmacokinetics===
The [[drug metabolism|metabolism]] of MBDB has been described in the [[scientific literature]].<ref>{{cite journal | vauthors = Lai FY, Erratico C, Kinyua J, Mueller JF, Covaci A, van Nuijs AL | title = Liquid chromatography-quadrupole time-of-flight mass spectrometry for screening in vitro drug metabolites in humans: investigation on seven phenethylamine-based designer drugs | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 114 | pages = 355–75 | date = October 2015 | pmid = 26112925 | doi = 10.1016/j.jpba.2015.06.016 | url = https://espace.library.uq.edu.au/view/UQ:365495/UQ365495_OA.pdf | hdl = 10067/1278220151162165141 | hdl-access = free }}</ref>

==Legal status==
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.<ref>{{cite web | author = WHO Expert Committee on Drug Dependence | url = http://whqlibdoc.who.int/trs/WHO_TRS_903.pdf | title = Thirty-second Report, Technical Report Series 903 | date = 2001 }}</ref> 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.''

===Australia===
MBDB is considered a Schedule 9 Prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">{{cite web | title = Poisons Standard | date = October 2015 | url = https://www.comlaw.gov.au/Details/F2015L01534 | work = Federal Register of Legislation | publisher = Australian Government }}</ref> 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.<ref name="Poisons Standard" />

===Finland===
Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>{{cite web | url=https://finlex.fi/fi/lainsaadanto/2014/1130 | title=1130/2014 }}</ref>

===Russia===
MBDB is included into  Schedule 1 of the Controlled Substances Act.<ref>[[:ru:MBDB]]{{circular reference|date=May 2024}}</ref>

===Sweden===
[[Riksdag|''Sveriges riksdags'']] health ministry ''{{ill|Statens folkhälsoinstitut|sv|Statens folkhälsoinstitut|vertical-align=sup}}'' classified MBDB as "health hazard" under the act ''{{ill|Lagen om förbud mot vissa hälsofarliga varor|sv|Lagen om förbud mot vissa hälsofarliga varor|vertical-align=sup}}'' (translated ''Act 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.<ref>{{cite web | title = Svensk författningssamling | trans-title = Swedish Code of Statutes | language = sv | url = http://www.notisum.se/rnp/sls/sfs/19990058.pdf | publisher = Notisum AB | access-date = 2013-09-25 | archive-date = 2018-03-06 | archive-url = https://web.archive.org/web/20180306142840/http://www.notisum.se/rnp/sls/sfs/19990058.pdf | url-status = dead }}</ref>

==Research==
MBDB is being assessed by PharmAla Biotech for potential medical use as a [[pharmaceutical drug]], for instance to treat [[autism]].<ref name="KaurKarabulutGauld2023" /><ref name="GobeNewswire2023">{{cite press release | author=PharmAla Biotech | title=Patent Application Published for PharmAla Biotech's MDMA Analogs | website=GlobeNewswire News Room | date=23 February 2023 | url=https://www.globenewswire.com/news-release/2023/02/23/2614222/0/en/Patent-Application-Published-for-PharmAla-Biotech-s-MDMA-Analogs.html | access-date=10 November 2024}}</ref><ref name="GlobeNewswire2024">{{cite press release | author=PharmAla Biotech | title=PharmAla Biotech Signs Sale Agreement with Numinus | website=GlobeNewswire News Room | date=26 March 2024 | url=https://www.globenewswire.com/news-release/2024/03/26/2852377/0/en/PharmAla-Biotech-Signs-Sale-Agreement-with-Numinus.html | access-date=10 November 2024}}</ref><ref name="CarkShawFantegrossi2024">{{cite conference | vauthors = Clark MR, Shaw HE, Fantegrossi WE | title = Poster 21: In vivo characterization of MBDB and its enantiomers in C57BL/6 and autism-like BTBR T<sup>+</sup>Itpr3<sup>tf</sup>/J mice | conference = 16th Annual Behavior, Biology, and Chemistry: Translational Research in Substance Use Disorders, San Antonio, Texas, Embassy Landmark, 22-24 March 2024 | date = March 2024 | url = https://ww2.uthscsa.edu/ARTT/BBC/print/2024Program.pdf#page=21}}</ref>

== See also ==
* [[Ethylbenzodioxolylbutanamine]] (EBDB; Ethyl-J)
* [[Methylbenzodioxolylpentanamine]] (MBDP; Methyl-K)
* [[UWA-101]]

== References ==
{{Reflist|2}}

== External links ==
* [http://www.erowid.org/library/books_online/pihkal/pihkal128.shtml PiHKAL entry]
* [http://pihkal.info/read.php?domain=pk&id=128 METHYL-J (MBDB) entry in PiHKAL • info]
* [http://www.erowid.org/chemicals/mbdb/mbdb.shtml Erowid MBDB vault]

{{Entactogens}}
{{Monoamine releasing agents}}
{{Monoamine neurotoxins}}
{{Phenethylamines}}

[[Category:Designer drugs]]
[[Category:Entactogens]]
[[Category:Experimental drugs]]
[[Category:Experimental entactogens]]
[[Category:Methylenedioxyphenethylamines]]
[[Category:Monoaminergic neurotoxins]]
[[Category:Phenylisobutylamines]]
[[Category:Serotonin-norepinephrine releasing agents]]