1,3-Benzodioxolylbutanamine

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.

1,3-Benzodioxolylbutanamine

Clinical data
Routes of administration	Oral
Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A US: Analogue to a Schedule I/II drug
Identifiers
IUPAC name 1-(1,3-Benzodioxol-5-yl)butan-2-amine
CAS Number	107447-03-0 Y HCl: 42542-07-4 Y
PubChem CID	129870
ChemSpider	114963
UNII	CM58WOT28Y HCl: RFD67T622Z Y
CompTox Dashboard (EPA)	DTXSID30910325
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image
Melting point	159 to 161 °C (318 to 322 °F)
SMILES CCC(CC1=CC2=C(C=C1)OCO2)N
InChI InChI=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 Key:VHMRXGAIDDCGDU-UHFFFAOYSA-N
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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.^[3] 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 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").^[4] 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.^[5][6] 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.^[7]