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
Routes of
administration
Oral
Legal status
Legal status
Identifiers
CAS Number 42542-07-4
PubChem CID 129870
ChemSpider 114963
Chemical data
Formula C11H15NO2
Molar mass 193.242 g/mol
Physical data
Melting point 159 to 161 °C (318 to 322 °F)
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1,3-Benzodioxolylbutanamine (also known as 3,4-methylenedioxybutanphenamine, MDB, BDB, J, and 3,4-methylenedioxy-α-ethylphenethylamine) is an entactogenic drug of the phenethylamine chemical class.[1][2] It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.

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 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, M. E.; Jiang, W; Deruiter, J; Clark, C. R. (1995). "A behavioral comparison of Nexus, cathinone, BDB, and MDA". Pharmacology, biochemistry, and behavior. 51 (2–3): 473–5. PMID 7667371. 
  3. ^ Bronson, M. E.; Jiang, W; Deruiter, J; Clark, C. R. (1995). "Structure-activity relationships of BDB and its monomethyl and dimethyl derivatives". Pharmacology, biochemistry, and behavior. 51 (2–3): 477–9. PMID 7667372. 
  4. ^ Kintz, P (1997). "Excretion of MBDB and BDB in urine, saliva, and sweat following single oral administration". Journal of analytical toxicology. 21 (7): 570–5. PMID 9399128. 
  5. ^ Garofano, L; Santoro, M; Patri, P; Guidugli, F; Bollani, T; Favretto, D; Traldi, P (1998). "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. 12 (12): 779–82. doi:10.1002/(SICI)1097-0231(19980630)12:12<779::AID-RCM233>3.0.CO;2-Q. PMID 9650303. 
  6. ^ Kronstrand, R (1996). "Identification of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB) in urine from drug users". Journal of analytical toxicology. 20 (6): 512–6. PMID 8889691. 

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