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

Maurer, HH; Kraemer, T; Springer, D; Staack, RF. Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (Ecstasy), piperazine, and pyrrolidinophenone types. A synopsis. Ther. Drug Monit., 1 Apr 2004, 26 (2), 127–131. 121 kB.

Trachsel, D. Fluorine in psychedelic phenethylamines. Drug Test. Analysis, 1 Jul 2012, 4 (7-8), 577-590. 1.0 MB. https://doi.org/10.1002/dta.413

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-hydroxytryptamine1A receptor-mediated behavioural 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

Nichols, DE; Hoffman, AJ; Oberlender, RA; Jacob, P; Shulgin, AT. Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: Representatives of a novel therapeutic class. J. Med. Chem., 1 Jan 1986, 29 (10), 2009–2015. 1.0 MB. https://doi.org/10.1021/jm00160a035

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 Jan 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 Jan 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., 1 Jan 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., 1 Jan 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.

Anon. 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

Ogino, M; Naiki, T; Orui, H; Kosone, K; Yamazaki, M. Study of method for identifying phenethylamine drugs. JCCL, , 50, 63-82. 627 kB. Retrieved from http://www.customs.go.jp/ccl_search/e_info_search/drugs/r_50_08_e.pdf

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

King, LA. New phenethylamines in Europe. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

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

Nichols, DE; Oberlender, R. Structure-activity relationships of MDMA-like substances. In Pharmacology and Toxicology of Amphetamine and Related Designer Drugs. NIDA Research Monograph 94; Asghar, K; De Souza, E, Eds., U.S. Department of Health and Human Services, National Institute of Health, U.S. Government Printing Office, Washington, DC, 1989; pp 12–40. 282 kB. #3

Simmler, LD; Liechti, ME. Pharmacology of MDMA- and amphetamine-like new psychoactive substances. In Handbook of Experimental Pharmacology; , Springer Berlin Heidelberg, 1 Jan 2018; . 298 kB. https://doi.org/10.1007/164_2018_113

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
2,5-DMA-hemiFly-5 · SF
G-1
M-7
N-Et-ADTN
DMMH-4 · Salsolidine
DMHM-4
2280
1095
1084
1006
10595
736
DV
TMDA
10183
10077
Mexedrone
3-MeO-PM
N-Methoxymephedrone
12190
MOMMC
Ethedrone
Dimethedrone
β-homo-MDMA
21 August 2018 · Creative Commons BY-NC-SA ·