1,3-Benzodioxolylbutanamine

1,3-Benzodioxolylbutanamine
Systematic (IUPAC) name
	1-(1,3-Benzodioxol-5-yl)butan-2-amine
Clinical data
Legal status	DE: Anlage I (Controlled); UK: Class A; Controlled Drug Analogue;
Routes of; administration	Oral
Identifiers
CAS Number	42542-07-4
PubChem	CID: 129870
ChemSpider	114963
Chemical data
Formula	C11H15NO2
Molecular mass	193.242 g/mol
	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 ;
Physical data
Melting point	159 to 161 °C (318 to 322 °F)
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1,3-Benzodioxolylbutanamine, 3,4-Methylenedioxybutanphenamine, MDB, (BDB; J; 3,4-methylenedioxy-α-ethyl phenethylamine) is an entactogenic drug of the phenethylamine chemical class.^[1]^[2] It is the α-ethyl analogue of methylenedioxyphenethylamine (MDPEA) and MDA.

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").^[3] 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.^[4]^[5] 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.^[6]

References

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↑ 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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

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[1] Lua error in package.lua at line 80: module 'strict' not found.

[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.

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v t e Entactogens
Phenylalkylamines	Phenethylamines: Lophophine MDMPEA MDPEA Metaescaline Amphetamines: 2-Methyl-MDA 4-FA 4-FMA 4-MTA 5-APDI 5-MAPDI 5-Methyl-MDA 6-APT 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EDA EDMA MDA MDDM MDEA MDIP MDMA MDMOH MDOH MDPR MMA MMDA MMDA-2 MMDMA PMA PMEA PMMA Benzofurans: 5-APB 5-MAPB 5-APDB 5-MAPDB 5-EAPB 6-APB 6-MAPB 6-APDB 6-MAPDB 6-EAPB Cathinones: Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone Pentylone Others: 4-CAB Ariadne BDB EBDB EBDP MDMP MDPH MBDB MBDP
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Tryptamines	4-Methyl-αET αET αMT
Others	Naphthylisopropylamine Methamnetamine

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamine Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-IT 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-MAPB 6-MAPDB EDA IAP MDA MDEA MDHMA MDMA MDOH MMDMA Naphthylaminopropane TAP Others: Amiflamine DFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Theodrenaline Thiamphenicol UWA-101

1,3-Benzodioxolylbutanamine

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