1,3-Benzodioxolylbutanamine

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1,3-Benzodioxolylbutanamine
BDB.svg
Systematic (IUPAC) name
1-(1,3-Benzodioxol-5-yl)butan-2-amine
Clinical data
Legal status Controlled Drug Analogue
Routes Oral
Identifiers
CAS number 42542-07-4
ATC code ?
PubChem CID 129870
ChemSpider 114963
Chemical data
Formula C11H15NO2 
Mol. mass 193.242 g/mol
Physical data
Melt. point 159–161 °C (318–322 °F)
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1,3-Benzodioxolylbutanamine, 3,4-Methylenedioxybutanphenamine, MDB, (BDB; J; 3,4-methylenedioxy-α-ethylphenethylamine) is an entactogenic drug of the phenethylamine chemical class.[1][2] It is the α-ethyl analogue of methylenedioxyphenethylamine (MDPEA) and MDA.

BDB was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the dosage range is listed as 150–230 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 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 potent serotonin releasing agent than its methylated sister compound methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J").[3] However, it is more commonly known as a metabolite of the N-alkylated analogues MBDB and ethylbenzodioxylbutanamine (EBDB; "Ethyl-J") which have appeared in so-called methylenedioxymethamphetamine (MDMA; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") tablets.[4][5] 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.[6]

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References[edit]

  1. ^ Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.

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