1,3-Benzodioxolylbutanamine

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 ; HCl: 42542-07-4 ;
PubChem CID	129870;
ChemSpider	114963;
UNII	CM58WOT28Y; HCl: RFD67T622Z ;
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;
	(verify)

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, amphetamine, and phenylisobutylamine families.^[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, 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]

Legal status

1,3-Benzodioxolylbutanamine is illegal in Germany (Anlage I)

References

^ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ Bronson ME, Jiang W, DeRuiter J, Clark CR (1995). "A behavioral comparison of Nexus, cathinone, BDB, and MDA". Pharmacology, Biochemistry, and Behavior. 51 (2–3): 473–5. doi:10.1016/0091-3057(95)00013-m. PMID 7667371. S2CID 32246652.
^ J entry in PiHKAL
^ Bronson ME, Jiang W, DeRuiter J, Clark CR (1995). "Structure-activity relationships of BDB and its monomethyl and dimethyl derivatives". Pharmacology, Biochemistry, and Behavior. 51 (2–3): 477–9. doi:10.1016/0091-3057(95)00012-l. PMID 7667372. S2CID 25332862.
^ 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. doi:10.1093/jat/21.7.570. PMID 9399128.
^ 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.
^ Kronstrand R (October 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. doi:10.1093/jat/20.6.512. PMID 8889691.