1,3-Benzodioxolylbutanamine

BDB
Clinical data
Other namesBDB; MDB; J; 3,4-Methylenedioxy-α-ethylphenethylamine; MDAEPEA; Benzodioxolylbutanamine; 3,4-Methylenedioxybutanphenamine
Routes of
administration		Oral[1]
Drug classSerotonin–norepinephrine releasing agent; Entactogen
Legal status
Legal status
Identifiers
  • 1-(1,3-benzodioxol-5-yl)butan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
Melting point159 to 161 °C (318 to 322 °F)
  • CCC(CC1=CC2=C(C=C1)OCO2)N
  • 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 (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]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BDB's dose as 150 to 230 mg orally and its 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]

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]

Synthesis

The chemical synthesis of BDB has been described.[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]

Germany

BDB is illegal in Germany (Anlage I).

See also

References

  1. ^ a b c d e f g h i j Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml
  2. ^ 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.
  3. ^ Kolaczynska KE, Ducret P, Trachsel D, Hoener MC, Liechti ME, Luethi D (June 2022). "Pharmacological characterization of 3,4-methylenedioxyamphetamine (MDA) analogs and two amphetamine-based compounds: N,α-DEPEA and DPIA". Eur Neuropsychopharmacol. 59: 9–22. doi:10.1016/j.euroneuro.2022.03.006. PMID 35378384.
  4. ^ a b Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  5. ^ 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.
  6. ^ Hardman HF, Haavik CO, Seevers MH (June 1973). "Relationship of the structure of mescaline and seven analogs to toxicity and behavior in five species of laboratory animals". Toxicol Appl Pharmacol. 25 (2): 299–309. Bibcode:1973ToxAP..25..299H. doi:10.1016/s0041-008x(73)80016-x. hdl:2027.42/33868. PMID 4197635.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
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