Exploring MBDB. To explore a different substance…

Names:
METHYL-J
MBDB
MDMB
Eden
2-Methylamino-1-(3,4-methylenedioxyphenyl)butane
N-Methyl-α-ethyl-3,4-methylenedioxyphenethylamine
N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
IUPAC names:
1-(2H-1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine
1-(1,3-Benzodioxol-5-yl)-N-methylbutan-2-amine
128 · C12H17NO2 · 207.269
InChI=1S/C12H17NO2/c1-3-10(13-2)6-9-4-5-11-12(7-9)15-8-14-11/h4-5,7,10,13H,3,6,8H2,1-2H3
USWVWJSAJAEEHQ-UHFFFAOYSA-N This stereoisomer Any stereoisomer
CCC(Cc1ccc2c(c1)OCO2)NC

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Shulgin, AT; Manning, T; Daley, PF. The Shulgin Index, Vol. 1, #76. MBDB. Erowid, 1 Jun 2011.

Johnson, MP; Hoffman, AJ; Nichols, DE. Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur. J. Pharmacol., 16 Dec 1986, 132 (2–3), 269–276. 559 kB. https://doi.org/10.1016/0014-2999(86)90615-1

Marona-Lewicka, D; Kurrasch-Orbaugh, DM; Selken, JR; Cumbay, MG; Lisnicchia, JG; Nichols, DE. Re-evaluation of lisuride pharmacology: 5-hydroxytryptamine 1A receptor-mediated behavioral effects overlap its other properties in rats. Psychopharmacology, 1 Oct 2002, 164 (1), 93–107. 293 kB. https://doi.org/10.1007/s00213-002-1141-z

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Nichols, DE. Differences between the mechanism of action of MDMA, MBDB, and the classic hallucinogens. Identification of a new therapeutic class: Entactogens. J. Psychoactive Drugs, 1 Oct 1986, 18 (4), 305–313. 10.7 MB. https://doi.org/10.1080/02791072.1986.10472362

Johnson, MP; Nichols, DE. Neurotoxic effects of the alpha-ethyl homologue of MDMA following subacute administration. Pharmacol. Biochem. Behav., 1 May 1989, 33 (1), 105–108. 399 kB. https://doi.org/10.1016/0091-3057(89)90437-1

Johnson, MP; Conarty, PF; Nichols, DE. [3H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur. J. Pharmacol., 23 Jul 1991, 200 (1), 9–16. 1.1 MB. https://doi.org/10.1016/0014-2999(91)90659-E

Nash, JF; Nichols, DE. Microdialysis studies on 3,4-methylenedioxyamphetamine and structurally related analogues. Eur. J. Pharmacol., 23 Jul 1991, 200 (1), 53–58. 714 kB. https://doi.org/10.1016/0014-2999(91)90664-C

Marona-Lewicka, D; Rhee, G; Sprague, JE; Nichols, DE. Reinforcing effects of certain serotonin-releasing amphetamine derivatives. Pharmacol. Biochem. Behav., 1 Jan 1996, 53 (1), 99–105. 1.0 MB. https://doi.org/10.1016/0091-3057(95)00205-7

Al-Hossaini, AM. GC-MS and GC-IRD studies on ethoxyphenethylamines related to MDEA, MDMMA and MBDB. Ph. D. Thesis, Auburn University, Auburn, AL, USA, 18 Dec 2009. 1.2 MB.

Schmidt, WJ; Mayerhofer, A; Meyer, A; Kovar, K. Ecstasy counteracts catalepsy in rats, an anti-parkinsonian effect? Neurosci. Lett., 27 Sep 2002, 330 (3), 251–254. 280 kB. https://doi.org/10.1016/S0304-3940(02)00823-6

Oberlender, R; Nichols, DE. (+)-N-Methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine as a discriminative stimulus in studies of 3,4-methylenedioxymethamphetamine-like behavioral activity. J. Pharmacol. Exp. Ther., 1 Dec 1990, 255 (3), 1098–1106. 1.9 MB.

EMCDDA. Report on the risk assessment of MBDB, European Monitoring Centre for Drugs and Drug Addiction, Jun 1999. 40 kB.

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. https://doi.org/10.1016/j.forsciint.2011.11.003

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Gandy, MN; Mclldowie, M; Lewis, K; Wasik, AM; Salomonczyk, D; Wagg, K; Millar, ZA; Tindiglia, D; Huot, P; Johnston, T; Thiele, S; Nguyen, B; Barnes, NM; Brotchie, JM; Martin-Iverson, MT. Redesigning the designer drug ecstasy: non-psychoactive MDMA analogues exhibiting Burkitt’s lymphoma cytotoxicity. Med. Chem. Comm., 2010, 1 (4), 287–293. 177 kB. https://doi.org/10.1039/c0md00108b

Thigpen, AL; Awad, T; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric methoxy-methyl-phenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 Nov 2008, 46 (10), 900–206. 448 kB. https://doi.org/10.1093/chromsci/46.10.900

Thigpen, AL; DeRuiter, J; Clark, CR. GC-MS studies on the regioisomeric 2,3- and 3,4-methylenedioxyphenethylamines related to MDEA, MDMMA, and MBDB. J. Chromatogr. Sci., 1 May 2007, 45 (5), 229–235. 332 kB. https://doi.org/10.1093/chromsci/45.5.229

Marona-Lewicka, D; Nichols, DE. Drug discrimination studies of the interoceptive cues produced by selective serotonin uptake inhibitors and selective serotonin releasing agents. Psychopharmacology, 1 Jul 1998, 138 (1), 67–75. 129 kB. https://doi.org/10.1007/s002130050646 #MBDB

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Clark, CR. Synthesis and analytical profiles for regioisomeric and isobaric amines related to MDMA, MDEA and MBDB: Differentiation of drug and non-drug substances of mass spectral equivalence, US DOJ, 1 Oct 2011. 3.9 MB. #8.2-7

Wasik, AM; Gandy, MN; McIldowie, M; Holder, MJ; Chamba, A; Challa, A; Lewis, KD; Young, SP; Scheel-Toellner, D; Dyer, MJ; Barnes, NM; Piggott, MJ; Gordon, J. Enhancing the anti-lymphoma potential of 3,4-methylenedioxymethamphetamine (‘ecstasy’) through iterative chemical redesign: mechanisms and pathways to cell death. Invest. New Drugs, 1 Aug 2012, 30 (4), 1471-1483. 575 kB. https://doi.org/10.1007/s10637-011-9730-5 #3

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Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1 Jan 1994; pp 3–41. 6.9 MB. #17

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Machiko, N; Takako, S; Misako, T; Suzuki, H; Yasuda, I. Analytical methods and spectrum data of 4 Governor-designated drugs. Ann. Rep. Tokyo Metr. Inst. P. H., 1 Jan 2005, 56 59–64. 1.9 MB. #MBDB

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Baudot, P; Vicherat, A; Viriot, M; Carré, M. Identification of N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine (MBDB), an homologue derivative of “ecstasy”. Analusis, 1 Jul 1999, 27 (6), 523–532. 107 kB. https://doi.org/10.1051/analusis:1999129 #MBDB GC,LC,MS,NMR

DMCPA
MADAM-6
MDDM
MDE
MDMC
MDMP
F
IDA
α-Pr-MDPEA
2C-G-2
MADAM-2
2C-VI
DOMAI · DOM-AI
4-MeO-3-Me-MCAT
5,8-ADT
MeO-B · 4-Methoxybuphedrone
DMA-2-hemiFLY
4-Propoxycathinone
α-Me-N-Pr-MDBA
α,α,N,N-TMMDBA
HMDMA
α-Me-N-iPr-MDBA
BO3A
Hordenine acetate
2,3-MDDMA
2,3-MDE
2,3-MBDB
MAPEA
N-Me-N-Et-MDPEA
N-Pr-MDPEA
N-iPr-MDPEA
α-Et-α-Me-MDPEA
α-iPr-MDPEA
ED-N-DMPEA
DMA-hemiFly-5 · DOH-5-hemiFLY
G-1
M-7
N-Et-ADTN
DMMH-4 · Salsolidine
DMHM-4
2280
1095
1084
1006
10595
736
DV
TMDA
10183
2CH-Ind
Mexedrone
3-MeO-PM
N-Methoxymephedrone
12190
MOMMC
Ethedrone
Dimethedrone
β-homo-MDMA
p4-605: METHYL-J
15 October 2018 · Creative Commons BY-NC-SA ·