1,3-Benzodioxolylbutanamine: Difference between revisions

| verifiedrevid = 424661842

| IUPAC_name = 1-(1,3-benzodioxol-5-yl)butan-2-amine

| image = BDB (psychedelic).png

| legal_status = Controlled Drug Analogue

| CAS_number = 42542-07-4

| molecular_weight = 193.242 g/mol

'''Benzodioxolylbutanamine''' ('''BDB'''; '''J'''; '''3,4-[[methylenedioxy]]-[[alpha carbon|α]]-[[ethyl group|ethyl]][[phenethylamine]]''') is an [[entactogen]], [[psychedelic drug|psychedelic]], and [[stimulant]] of the [[phenethylamine]] [[chemical class]].<ref>{{CitePiHKAL}}</ref><ref>Bronson ME, Jiang W, DeRuiter J, Clark CR. A behavioral comparison of Nexus, cathinone, BDB, and MDA. Pharmacology, Biochemistry and Behaviour. 1995 Jun-Jul;51(2-3):473-5.</ref> It is the [[alpha carbon|α]]-[[ethyl group|ethyl]] [[analogue (chemistry)|analogue]] of [[methylenedioxyphenethylamine]] (MDPEA) and [[methylenedioxyamphetamine]] (MDA; Tenamfetamine; "Hug Drug", "Love Drug").

BDB was first synthesized by [[Alexander Shulgin]]. In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', the dosage range is listed as 150–230&nbsp;mg, and the duration is listed as 4–8 hours. BDB produces [[entactogenic]], [[MDMA]]-like effects. While pleasant and euphoric, BDB is also fairly sedating and some users feel that the lack of stimulant effect makes it less enjoyable than other similar drugs. Additional side effects associated with BDB include [[pathologic nystagmus|nystagmus]] and [[dizziness]]. Very little data exists about the pharmacological properties, metabolism, and toxicity of BDB.

Animal studies and anecdotal reports show that BDB is a slightly more [[potency (pharmacology)|potent]] [[serotonin]] [[releasing agent]] than its [[methylated]] sister [[chemical compound|compound]] [[methylbenzodioxylbutanamine]] (MBDB; "Eden", "Methyl-J").<ref>Bronson ME, Jiang W, DeRuiter J, Clark CR. Structure-activity relationships of BDB and its monomethyl and dimethyl derivatives. Pharmacology, Biochemistry and Behaviour. 1995 Jun-Jul;51(2-3):477-9.</ref> However, it is more commonly known as a [[metabolite]] of the ''N''-[[alkyl]]ated analogues MBDB and [[ethylbenzodioxylbutanamine]] (EBDB; "Ethyl-J") which have appeared in so-called [[methylenedioxymethamphetamine]] (MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets.<ref>Kintz P. Excretion of MBDB and BDB in urine, saliva, and sweat following single oral administration. Journal of Analytical Toxicology. 1997 Nov-Dec;21(7):570-5.</ref><ref>Garofano L, Santoro M, Patri P, Guidugli F, Bollani T, Favretto D, Traldi P. Ion trap mass spectrometry for the characterization of N-methyl-1- (3,4-methylene-dioxyphenyl)-2-butanamine and N-ethyl-3,4- methylenedioxyamphetamine, two widely distributed street drugs. Rapid Communications in Mass Spectrometry. 1998;12(12):779-82.</ref> While BDB itself has not been reported as being sold as "Ecstasy", urine analysis of "Ecstasy" users suggest that this drug may have appeared as a street drug, although it is unclear whether the positive urine test for BDB resulted from consumption of BDB itself or merely as a metabolite of MBDB.<ref>Kronstrand R. Identification of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB) in urine from drug users. Journal of Analytical Toxicology. 1996 Oct;20(6):512-6.</ref>

==See also==

* [[alpha-Ethylphenethylamine|α-Ethylphenethylamine]]

* [[Ethylbenzodioxolylbutanamine]] (EBDB; Ethyl-J)

* [[Methylbenzodioxolylbutanamine]] (MBDB; Methyl-J; "Eden")

==References==

{{reflist|2}}

==External links==

* [http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml J entry in ''PiHKAL'']

* [http://pihkal.info/read.php?domain=pk&id=94 J entry in PiHKAL • info]

{{Stimulants}}

{{Adrenergics}}

{{Dopaminergics}}

{{Serotonergics}}

{{Methylenedioxyphenethylamines}}

{{PiHKAL}}

{{pharm-stub}}

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