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1,3-Benzodioxolylbutanamine

Clinical data
Routes of administration	Oral
Legal status
Legal status	Controlled Drug Analogue
Identifiers
IUPAC name 1-(1,3-benzodioxol-5-yl)butan-2-amine
CAS Number	42542-07-4
PubChem CID	129870
CompTox Dashboard (EPA)	DTXSID30910325
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.242 g/mol g·mol
3D model (JSmol)	Interactive image
Melting point	159 to 161 °C (318 to 322 °F)
SMILES CCC(CC1=CC2=C(C=C1)OCO2)N
(verify)

Benzodioxolylbutanamine (BDB; J; 3,4-methylenedioxy-α-ethylphenethylamine) is an entactogen, psychedelic, and stimulant of the phenethylamine chemical class. It is the α-ethyl analogue of methylenedioxyphenethylamine (MDPEA) and methylenedioxyamphetamine (MDA; Tenamfetamine; "Hug Drug", "Love Drug").

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"). 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. 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.

See also

• α-Ethylphenethylamine
• 1-(4-Methylphenyl)-2-aminobutane
• Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J)
• Methylbenzodioxolylbutanamine (MBDB; Methyl-J; "Eden")

References

1. Shulgin, Alexander; Shulgin, Ann (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.

External links

• J entry in PiHKAL
• J entry in PiHKAL • info

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