Entactogen drug
Pharmaceutical compound
1,3-Benzodioxolylbutanamine (BDB ), also known as3,4-methylenedioxy-α-ethylphenethylamine or asJ , is anentactogen of thephenethylamine ,phenylisobutylamine , andMDxx families related toMDMA .[ 1] [ 2]
In his bookPiHKAL Phenethylamines I Have Known and Loved ),Alexander Shulgin lists the dose range as 150 to 230 mgorally and theduration as 4 to 8 hours.[ 1] [ 1] euphoric , BDB is also fairlysedating and some users feel that the lack ofstimulant effect makes it less enjoyable than other similar drugs.[ 1] side effects associated with BDB includenystagmus anddizziness .[ 1] pharmacological properties,metabolism , andtoxicity of BDB.[ 1]
Receptor andtransporter interaction data have been reported for BDB.[ 3] [ 4] serotonin–norepinephrine releasing agent (SNDRA) with only weak effects ondopamine .[ 4] Animal studies andanecdotal reports have found that BDB is a slightly morepotent serotonin releasing agent than itsmethylated sistercompound methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J").[ 5]
BDB, also known as 1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-α-ethylphenethylamine, is aphenethylamine ,α-ethylphenethylamine (phenylisobutylamine), andmethylenedioxyphenethylamine (MDxx) related toMDMA .[ 1] α -ethyl analogue of3,4-methylenedioxyphenethylamine (MDPEA) and3,4-methylenedioxyamphetamine (MDA) and the 3,4-methylenedioxy derivative ofα-ethylphenethylamine (AEPEA).[ 1]
Analogues of BDB includeMBDB (methyl-J),EBDB (ethyl-J),1,3-benzodioxolylpentanamine (BDP; K),MBDP (methyl-K),EBDP (ethyl-K), andMPAP (PDBP; propyl-K), among others.[ 1]
BDB was first described in thescientific literature by at least 1973.[ 6]
Society and culture [ edit ] Rather than as arecreational drug itself, BDB is more commonly known as ametabolite of theN -alkylated analogues MBDB andethylbenzodioxylbutanamine (EBDB; "Ethyl-J"), which have appeared in MDMA or "ecstasy" tablets.[ 7] [ 8] [ 9]
BDB is illegal inGermany (Anlage I ).
^a b c d e f g h i j Shulgin A ,Shulgin A (September 1991).PiHKAL: A Chemical Love Story ISBN 0-9630096-0-5 OCLC 25627628 .http://www.erowid.org/library/books_online/pihkal/pihkal094.shtml ^ 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 . ^ 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 . ^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 . ^ 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 . ^ 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 . ^ 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 .
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )
