Chemistry:Homo-MDMA
Homo-MDMA (HMDMA), also known as α,N-dimethyl-3-(3,4-methylenedioxyphenyl)propylamine, is an entactogen-like drug of the phenylpropylamine group related to MDMA.[1][2] It is an analogue of MDMA in which the side chain has been lengthened by one carbon atom.[1][2]
It showed very weak induction of serotonin release (much less than that of MDMA or methamphetamine) and no significant release of dopamine in rat brain synaptosomes.[1][3] As such, its monoamine-releasing activity was said to have been essentially abolished relative to MDMA.[3] The drug partially substituted for MDMA in rodent drug discrimination tests but produced seizures at high doses.[1][3]
Based on unpublished findings by Alexander Shulgin, homo-MDMA has been said to be inactive in humans.[1][3] However, it has been encountered as a designer and recreational drug in Japan and was being sold as "MBDB".[1][4] It is not a controlled substance in the United States as of 2011.[1]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "#83. Homo-MDMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley, CA: Transform Press. 2011. pp. 201–202. ISBN 978-0-9630096-3-0. OCLC 709667010. https://archive.org/details/shulgin-index-vol-1/page/201/mode/1up?view=theater.
- ↑ 2.0 2.1 "Behavioral and developmental effects of two 3,4-methylenedioxymethamphetamine (MDMA) derivatives". Drug Alcohol Depend 36 (3): 161–166. December 1994. doi:10.1016/0376-8716(94)90141-4. PMID 7889806.
- ↑ 3.0 3.1 3.2 3.3 "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacol Biochem Behav 38 (3): 505–512. March 1991. doi:10.1016/0091-3057(91)90005-m. PMID 1829838. "Extension of the side-chain of MDMA by one carbon to give the homologue HMDMA (41), or replacement of one methylenedioxy oxygen with sulfur to give the compound 4-T-MMDA-2 (Fig. 1) essentially abolishes the 3H-5-HT and 3H-DA releasing capability, as well as the central psychotropic effect in man (Shulgin and Jacob, unpublished). The possible neurotoxicity of these analogues is not addressed in the present study.".
- ↑ "Identification of N-Methyl-4-(3,4-Methylenedioxyphenyl)Butan-2-Amine, Distributed as MBDB". Journal of Health Science 52 (6): 805–810. 2006. doi:10.1248/jhs.52.805. ISSN 1344-9702. https://www.jstage.jst.go.jp/article/jhs/52/6/52_6_805/_pdf. Retrieved 3 February 2025.
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