1,3-Benzodioxolylbutanamine: Difference between revisions
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{{Short description|Enactogenic drug of the phenethylamine class}} |
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{{Drugbox |
{{Drugbox |
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| verifiedrevid = |
| verifiedrevid = 447759045 |
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| IUPAC_name = 1-(1,3- |
| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)butan-2-amine |
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| image = BDB |
| image = BDB.svg |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| legal_DE = Anlage I |
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| legal_status = Controlled Drug Analogue |
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| legal_UK = Class A |
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| legal_US = Analogue |
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| routes_of_administration = Oral |
| routes_of_administration = Oral |
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<!--Identifiers--> |
<!--Identifiers--> |
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| index2_label = HCl |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 107447-03-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CM58WOT28Y |
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| CAS_number2_Ref = {{cascite|correct|CAS}} |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = RFD67T622Z |
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| PubChem = 129870 |
| PubChem = 129870 |
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| ChemSpiderID = 114963 |
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| StdInChI = 1S/C11H15NO2/c1-2-9(12)5-8-3-4-10-11(6-8)14-7-13-10/h3-4,6,9H,2,5,7,12H2,1H3 |
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| StdInChIKey = VHMRXGAIDDCGDU-UHFFFAOYSA-N |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=11 | H=15 | N=1 | O=2 |
| C=11 | H=15 | N=1 | O=2 |
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| molecular_weight = 193.242 g/mol |
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| smiles = CCC(CC1=CC2=C(C=C1)OCO2)N |
| smiles = CCC(CC1=CC2=C(C=C1)OCO2)N |
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| melting_point = 159 |
| melting_point = 159 |
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'''Benzodioxolylbutanamine''' ('''BDB''' |
'''1,3-Benzodioxolylbutanamine''' (also known as '''3,4-methylenedioxybutanphenamine''', '''MDB''', '''BDB''', '''J''', and '''3,4-methylenedioxy-α-ethylphenethylamine''') is an [[Empathogen-entactogen|entactogen]]ic drug of the [[phenethylamine]] [[chemical class]].<ref>{{CitePiHKAL|name-list-style = vanc }}</ref><ref>{{cite journal | vauthors = Bronson ME, Jiang W, DeRuiter J, Clark CR | title = A behavioral comparison of Nexus, cathinone, BDB, and MDA | journal = Pharmacology, Biochemistry, and Behavior | volume = 51 | issue = 2–3 | pages = 473–5 | year = 1995 | pmid = 7667371 | doi = 10.1016/0091-3057(95)00013-m | s2cid = 32246652 }}</ref> It is the [[alpha carbon|α]]-[[ethyl group|ethyl]] [[structural analog|analog]] of [[MDPEA]] and [[3,4-Methylenedioxyamphetamine|MDA]] and the [[methylenedioxy]] analogue of [[alpha-Ethylphenethylamine|α-ethylphenethylamine]]. |
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BDB was first synthesized by [[Alexander Shulgin]]. In his book ''[[PiHKAL |
BDB was first synthesized by [[Alexander Shulgin]]. In his book ''[[PiHKAL]]'', the dosage range is listed as 150–230 mg and the duration is listed as 4–8 hours.<ref>[http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml J entry in ''PiHKAL'']</ref> BDB produces [[entactogenic]], [[MDMA]]-like effects. Although 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. |
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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 |
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>{{cite journal | vauthors = Bronson ME, Jiang W, DeRuiter J, Clark CR | title = Structure-activity relationships of BDB and its monomethyl and dimethyl derivatives | journal = Pharmacology, Biochemistry, and Behavior | volume = 51 | issue = 2–3 | pages = 477–9 | year = 1995 | pmid = 7667372 | doi = 10.1016/0091-3057(95)00012-l | s2cid = 25332862 }}</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 [[methylenedioxymethamphetamine]] (MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets.<ref>{{cite journal | vauthors = Kintz P | title = Excretion of MBDB and BDB in urine, saliva, and sweat following single oral administration | journal = Journal of Analytical Toxicology | volume = 21 | issue = 7 | pages = 570–5 | year = 1997 | pmid = 9399128 | doi = 10.1093/jat/21.7.570 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Garofano L, Santoro M, Patri P, Guidugli F, Bollani T, Favretto D, Traldi P | title = 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 | journal = Rapid Communications in Mass Spectrometry | volume = 12 | issue = 12 | pages = 779–82 | year = 1998 | pmid = 9650303 | doi = 10.1002/(SICI)1097-0231(19980630)12:12<779::AID-RCM233>3.0.CO;2-Q }}</ref> Although 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>{{cite journal | vauthors = Kronstrand R | title = Identification of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB) in urine from drug users | journal = Journal of Analytical Toxicology | volume = 20 | issue = 6 | pages = 512–6 | date = October 1996 | pmid = 8889691 | doi = 10.1093/jat/20.6.512 | doi-access = free }}</ref> |
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==Legal status== |
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1,3-Benzodioxolylbutanamine is illegal in Germany ([[Drugs controlled by the German Betäubungsmittelgesetz|Anlage I]]) |
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* [[alpha-Ethylphenethylamine|α-Ethylphenethylamine]] |
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== See also == |
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* [[1-(4-Methylphenyl)-2-aminobutane]] |
* [[1-(4-Methylphenyl)-2-aminobutane]] |
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* [[Ethylbenzodioxolylbutanamine]] (EBDB; Ethyl-J) |
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* [[Methylbenzodioxolylbutanamine]] (MBDB; Methyl-J; "Eden") |
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==References== |
== References == |
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{{ |
{{Reflist|2}} |
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==External links== |
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* [http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml J entry in ''PiHKAL''] |
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* [http://pihkal.info/read.php?domain=pk&id=94 J entry in PiHKAL • info] |
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{{Entactogens}} |
{{Entactogens}} |
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{{Monoamine releasing agents}} |
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{{Stimulants}} |
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{{Adrenergics}} |
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{{Dopaminergics}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
{{Phenethylamines}} |
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{{Methylenedioxyphenethylamines}} |
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{{PiHKAL}} |
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{{DEFAULTSORT:Benzodioxolylbutanamine, 1,3-}} |
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[[Category:Psychedelic phenethylamines]] |
[[Category:Psychedelic phenethylamines]] |
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[[Category:Benzodioxoles]] |
[[Category:Benzodioxoles]] |
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[[Category:Serotonin-norepinephrine-dopamine releasing agents]] |
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[[Category:Entactogens and empathogens]] |
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{{pharm-stub}} |
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[[de:2-Amino-1-(3,4-methylendioxyphenyl)butan]] |
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[[ru:БДБ]] |