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| Other names | HMDMA; MDP-3-MB; α,N-Dimethyl-3-(3,4-methylenedioxyphenyl)propylamine; α,N-Dimethyl-1,3-benzodioxole-5-propylamine |
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| Chemical and physical data | |
| Formula | C12H17NO2 |
| Molar mass | 207.273 g·mol−1 |
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Homo-MDMA (HMDMA), also known asα,N-dimethyl-3-(3,4-methylenedioxyphenyl)propylamine, is anentactogen-like drug of thephenylpropylamine group related toMDMA.[1][2] It is ananalogue of MDMA in which theside chain has been lengthened by onecarbonatom.[1][2]
It showed very weakinduction of serotonin release (much less than that of MDMA ormethamphetamine) and no significantrelease of dopamine in rat brainsynaptosomes.[1][3] As such, itsmonoamine-releasing activity was said to have been essentially abolished relative to MDMA.[3] The drug partially substituted for MDMA in rodentdrug discrimination tests but producedseizures at high doses.[1][3]
Based on unpublished findings byAlexander Shulgin, homo-MDMA has been said to be inactive in humans.[1][3] However, it has been encountered as adesigner andrecreational drug inJapan and was being sold as "MBDB".[1][4] It is not acontrolled substance in theUnited States as of 2011.[1]
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the 3H-5-HT and 3H-DA releasing capability, as well as the central psychotropic effect in man (Shulgin and Jacob, unpublished).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.
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