MDAI: Difference between revisions
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==Pharmacology== | ==Pharmacology== | ||
MDAI has been shown to [[Reuptake inhibitor|inhibit the reuptake] of [[serotonin]], [[dopamine]], and [[norepinephrine]]. This demonstrates that MDAI has selective affinity for the [[serotonin transporter]] (SERT). Studies show that the brains of animals treated with MDAI have greater extracellular concentrations of [[Neurotransmitter|monoamine neural transmitters]] resulted, most significantly [[serotonin]]. This result indicates that MDAI is a potent releaser of serotonin, while effectively inhibiting the reuptake of serotonin. For comparison, MDAI is similar in potency with releasing serotonin to [[MDA]] but significantly less potent than [[MDMA]].<ref>Johnson MP, Conarty PF, Nichols DE. [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur J Pharmacol. 1991 Jul 23;200(1):9-16. PMID 1685125</ref> | |||
==Subjective effects== | ==Subjective effects== | ||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||||
| Common names | MDMA, Molly, Mandy, Emma, MD, Ecstasy, E, X, XTC, Rolls, Beans, Pingers | ||||||||||||||||||||||||||||||||
| Substitutive name | 3,4-Methylenedioxy-N-methylamphetamine | ||||||||||||||||||||||||||||||||
| Systematic name | (RS)-1-(Benzo[d][1,3]dioxol-5-yl)-N-methylpropan-2-amine | ||||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||||
| Psychoactive class | Stimulant / Entactogen | ||||||||||||||||||||||||||||||||
| Chemical class | Amphetamine / MDxx | ||||||||||||||||||||||||||||||||
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| Serotonin releasers | |||||||||||||||||||||||||||||||||
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MDAI (5,6-Methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) which produces entactogen effects in humans similar to that of MDMA.
Chemistry
The chemical structure of MDAI is indirectly derived from that of the illicit drug MDA, but the alpha-methyl group of the alkylamino amphetamine side chain has been bound back to the benzene nucleus to form an indane ring system, which changes its pharmacological properties substantially.[1]
Pharmacology
MDAI has been shown to [[Reuptake inhibitor|inhibit the reuptake] of serotonin, dopamine, and norepinephrine. This demonstrates that MDAI has selective affinity for the serotonin transporter (SERT). Studies show that the brains of animals treated with MDAI have greater extracellular concentrations of monoamine neural transmitters resulted, most significantly serotonin. This result indicates that MDAI is a potent releaser of serotonin, while effectively inhibiting the reuptake of serotonin. For comparison, MDAI is similar in potency with releasing serotonin to MDA but significantly less potent than MDMA.[2]
Subjective effects
Toxicity and Harm Potential
MDAI and other similar drugs have been widely used in scientific research, as they are able to replicate many of the effects of MDMA, but without causing the neurotoxicity which may be associated with MDMA and some related drugs. No tests have been performed on cardiovascular toxicity.[3][4][5][6][7][8][9]
Lethal dosage
Tolerance and addition potential
Legal Issues
See Also
References
- ↑ Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. Journal of Medicinal Chemistry. 1993 Nov 12;36(23):3700-6. Template:DOI PMID 8246240
- ↑ Johnson MP, Conarty PF, Nichols DE. [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur J Pharmacol. 1991 Jul 23;200(1):9-16. PMID 1685125
- ↑ Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM. Nonneurotoxic tetralin and indan analogues of 3,4-(methylenedioxy)amphetamine (MDA). Journal of Medicinal Chemistry. 1990 Feb;33(2):703-10. PMID 1967651
- ↑ Nichols DE, Johnson MP, Oberlender R. 5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine. Pharmacology, Biochemistry and Behaviour. 1991 Jan;38(1):135-9. PMID 1826785
- ↑ Johnson MP, Frescas SP, Oberlender R, Nichols DE. Synthesis and Pharmacological Examination of 1-(3-Methoxy-4-methylphenyl)-2-aminopropane and 5-Methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(Methylenedioxy)methamphetamine (MDMA). Journal of Medicinal Chemistry 1991;34:1662-1668.
- ↑ Johnson MP, Huang XM, Nichols DE. Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a nonneurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analogue. Pharmacology, Biochemistry and Behaviour. 1991 Dec;40(4):915-22. PMID 1726189
- ↑ Nichols DE, Marona-Lewicka D, Huang X, Johnson MP. Novel serotonergic agents. Drug Design and Discovery. 1993;9(3-4):299-312. PMID 8400010
- ↑ Sprague JE, Johnson MP, Schmidt CJ, Nichols DE. Studies on the mechanism of p-chloroamphetamine neurotoxicity. Biochemical Pharmacology. 1996 Oct 25;52(8):1271-7. PMID 8937435
- ↑ Cozzi NV, Frescas S, Marona-Lewicka D, Huang X, Nichols DE. Indan analogs of fenfluramine and norfenfluramine have reduced neurotoxic potential. Pharmacology, Biochemistry and Behaviour. 1998 Mar;59(3):709-15. Template:DOI PMID 9512076