1,3-Benzodioxolylbutanamine

1,3-Benzodioxolylbutanamine (BDB), also known as 3,4-methylenedioxy-α-ethylphenethylamine or as J, is an entactogen of the phenethylamine, phenylisobutylamine, and MDxx families related to MDMA.^[1][2]

BDB

Clinical data
Other names	BDB; MDB; J; 3,4-Methylenedioxy-α-ethylphenethylamine; MDAEPEA; Benzodioxolylbutanamine; 3,4-Methylenedioxybutanphenamine
Routes of administration	Oral[1]
Drug class	Serotonin–norepinephrine releasing agent; Entactogen
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
ChEBI	CHEBI:190948
ChEMBL	ChEMBL61507
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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Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range as 150 to 230 mg orally and the duration as 4 to 8 hours.^[1] BDB produces entactogenic, MDMA-like effects.^[1] 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.^[1] Additional side effects associated with BDB include nystagmus and dizziness.^[1] Very little data exists about the pharmacological properties, metabolism, and toxicity of BDB.^[1]

Interactions

See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Pharmacology

Pharmacodynamics

Receptor and transporter interaction data have been reported for BDB.^[3][4] It acts as a serotonin–norepinephrine releasing agent (SNDRA) with only weak effects on dopamine.^[4] Animal studies and anecdotal reports have found that BDB is a slightly more potent serotonin releasing agent than its methylated sister compound methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J").^[5]

Chemistry

BDB, also known as 1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-α-ethylphenethylamine, is a phenethylamine, α-ethylphenethylamine (phenylisobutylamine), and methylenedioxyphenethylamine (MDxx) related to MDMA.^[1] It is the α-ethyl analogue of 3,4-methylenedioxyphenethylamine (MDPEA) and 3,4-methylenedioxyamphetamine (MDA) and the 3,4-methylenedioxy derivative of α-ethylphenethylamine (AEPEA).^[1]

Analogues

Analogues of BDB include MBDB (methyl-J), EBDB (ethyl-J), 1,3-benzodioxolylpentanamine (BDP; K), MBDP (methyl-K), EBDP (ethyl-K), and MPAP (PDBP; propyl-K), among others.^[1]

History

BDB was first described in the scientific literature by at least 1973.^[6]

Society and culture

Recreational use

Rather than as a recreational drug itself, BDB is more commonly known as a metabolite of the N-alkylated analogues MBDB and ethylbenzodioxylbutanamine (EBDB; "Ethyl-J"), which have appeared in MDMA or "ecstasy" tablets.^[7][8] Although BDB itself has not been reported as being sold as "ecstasy", urine analysis of users suggest that this drug may have appeared as a street drug, though it is unclear whether the positive urine test for BDB resulted from consumption of BDB itself or merely as a metabolite of MBDB.^[9]

Legal status

Germany

BDB is illegal in Germany (Anlage I).

See also

• Substituted methylenedioxyphenethylamine
• Substituted phenylisobutylamine