| Revision as of 00:33, 1 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'DrugBank_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Dr← Previous edit |
Latest revision as of 14:02, 10 November 2024 edit undoBunnypranav (talk | contribs)Extended confirmed users, Page movers, New page reviewers, Rollbackers7,426 edits Adding page to Category:Phenylisobutylamines as requested at WP:AFC/C (afcrc-helper) |
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{{Short description|Enactogenic drug of the phenethylamine class}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 424661842 |
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| verifiedrevid = 447759045 |
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| IUPAC_name = 1-(1,3-benzodioxol-5-yl)butan-2-amine |
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| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)butan-2-amine |
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| image = BDB (psychedelic).png |
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| image = BDB.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| 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 |
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| routes_of_administration = Oral |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| index2_label = HCl |
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| CAS_number = 42542-07-4 |
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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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| CAS_number2 = 42542-07-4 |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = RFD67T622Z |
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| PubChem = 129870 |
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| 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--> |
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<!--Chemical data--> |
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| C=11 | H=15 | N=1 | O=2 |
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| 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 |
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| smiles = CCC(CC1=CC2=C(C=C1)OCO2)N |
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| melting_point = 159 |
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| melting_point = 159 |
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'''Benzodioxolylbutanamine''' ('''BDB'''; '''J'''; '''3,4-]-]-]]''') is an ], ], and ] of the ] ].<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 ]-] ] of ] (MDPEA) and ] (MDA; Tenamfetamine; "Hug Drug", "Love Drug"). |
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'''1,3-Benzodioxolylbutanamine''' (also known as '''3,4-methylenedioxybutanphenamine''', '''MDB''', '''BDB''', '''J''', and '''3,4-methylenedioxy-α-ethylphenethylamine''') is an ]ic drug of the ], ], and ] families.<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 ]-] ] of ] and ] and the ] analogue of ]. |
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BDB was first synthesized by ]. In his book '']'', the dosage range is listed as 150–230 mg, and the duration is listed as 4–8 hours. BDB produces ], ]-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 ] and ]. Very little data exists about the pharmacological properties, metabolism, and toxicity of BDB. |
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BDB was first synthesized by ]. In his book '']'', the dosage range is listed as 150–230 mg and the duration is listed as 4–8 hours.<ref></ref> BDB produces ], ]-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 ] and ]. 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 ] ] ] than its ] sister ] ] (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 ] of the ''N''-]ated analogues MBDB and ] (EBDB; "Ethyl-J") which have appeared in so-called ] (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> |
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Animal studies and anecdotal reports show that BDB is a slightly more ] ] ] than its ] sister ] ] (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 ] of the ''N''-]ated analogues MBDB and ] (EBDB; "Ethyl-J") which have appeared in ] (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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==See also== |
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==Legal status== |
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1,3-Benzodioxolylbutanamine is illegal in Germany (]) |
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* ] |
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== See also == |
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* ] |
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* ] |
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* ] (EBDB; Ethyl-J) |
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* ] (MBDB; Methyl-J; "Eden") |
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==References== |
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== References == |
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{{reflist|2}} |
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{{Reflist|2}} |
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==External links== |
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{{Entactogens}} |
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{{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}} |
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{{Phenethylamines}} |
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{{Methylenedioxyphenethylamines}} |
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{{PiHKAL}} |
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{{DEFAULTSORT:Benzodioxolylbutanamine, 1,3-}} |
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