1,3-Benzodioxolylbutanamine

Entactogen drug 447759045 BDB BDB structure.svg skin-invert-image 225px BDB ball-and-stick structure.png bg-transparent 235px Oral Serotonin–norepinephrine releasing agent; Entactogen Anlage I Class A Analogue HCl correct CAS 107447-03-0 correct FDA CM58WOT28Y correct CAS 42542-07-4 correct FDA RFD67T622Z 129870 114963 190948 61507 BDB; MDB; J; 3,4-Methylenedioxy-α-ethylphenethylamine; MDAEPEA; Benzodioxolylbutanamine; 3,4-Methylenedioxybutanphenamine 1-(1,3-benzodioxol-5-yl)butan-2-amine 11 15 1 2 CCC(CC1=CC2=C(C=C1)OCO2)N 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 VHMRXGAIDDCGDU-UHFFFAOYSA-N 159 161 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. vanc http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml Bronson ME, Jiang W, DeRuiter J, Clark CR A behavioral comparison of Nexus, cathinone, BDB, and MDA Pharmacology, Biochemistry, and Behavior 51 2–3 473–5 1995 7667371 10.1016/0091-3057(95)00013-m 32246652 Use and effects In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists BDB's dose as 150 to 230mg orally and its duration as 4 to 8hours. 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. Interactions MDMA#Interactions Trip killer#Antidotes of other hallucinogens MDMA/citalopram Pharmacology Pharmacodynamics Receptor and transporter interaction data have been reported for BDB. Kolaczynska KE, Ducret P, Trachsel D, Hoener MC, Liechti ME, Luethi D Pharmacological characterization of 3,4-methylenedioxyamphetamine (MDA) analogs and two amphetamine-based compounds: N,α-DEPEA and DPIA Eur Neuropsychopharmacol 59 9–22 June 2022 35378384 10.1016/j.euroneuro.2022.03.006 https://www.researchgate.net/publication/359686098 free Nagai F, Nonaka R, Satoh Hisashi Kamimura K The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain Eur J Pharmacol 559 2–3 132–137 March 2007 17223101 10.1016/j.ejphar.2006.11.075 It acts as a serotonin–norepinephrine releasing agent (SNDRA) with only weak effects on dopamine. 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"). Bronson ME, Jiang W, DeRuiter J, Clark CR Structure-activity relationships of BDB and its monomethyl and dimethyl derivatives Pharmacology, Biochemistry, and Behavior 51 2–3 477–9 1995 7667372 10.1016/0091-3057(95)00012-l 25332862 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. 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). Synthesis The chemical synthesis of BDB has been described. 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. History BDB was first described in the scientific literature by at least 1973. Hardman HF, Haavik CO, Seevers MH 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 June 1973 4197635 10.1016/s0041-008x(73)80016-x 1973ToxAP..25..299H 2027.42/33868 free 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. Kintz P Excretion of MBDB and BDB in urine, saliva, and sweat following single oral administration Journal of Analytical Toxicology 21 7 570–5 1997 9399128 10.1093/jat/21.7.570 free 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 12 12 779–82 1998 9650303 10.1002/(SICI)1097-0231(19980630)12:12<779::AID-RCM233>3.0.CO;2-Q 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. Kronstrand R Identification of N-methyl-1-(3,4-methylenedioxyphenyl)-2-butanamine (MBDB) in urine from drug users Journal of Analytical Toxicology 20 6 512–6 October 1996 8889691 10.1093/jat/20.6.512 free Legal status Germany BDB is illegal in Germany (Anlage I). See also Substituted methylenedioxyphenethylamine Substituted phenylisobutylamine References External links J (BDB) - Isomer Design J (BDB) - PiHKAL - Erowid J (BDB) - PiHKAL - Isomer Design BDB (J) - The Shulgin Index Category:David E. Nichols Category:Designer drugs Category:Entactogens Category:Methylenedioxyamphetamines Category:Phenylisobutylamines Category:PiHKAL Category:Serotonin-norepinephrine releasing agents