5-Chloro-αMT is aserotonin–dopamine releasing agent (SDRA).[2] TheEC50Tooltip half-maximal effective concentration values of 5-chloro-αMT in evoking thein vitrorelease ofserotonin,dopamine, andnorepinephrine in rat brainsynaptosomes were reported as 16nM, 54nM, and 3,434nM, respectively.[2] It had a norepinephrine:dopamine ratio of 64:1 and a dopamine:serotonin ratio of 3.4:1, indicating that it is a highly specific and fairly well-balanced SDRA.[2]
However, 5-chloro-αMT has also been found to act as a potentfull agonist of the serotonin5-HT2A receptor, with an EC50 value of 6.27nM and amaximal efficacy of 105%.[1] As a serotonin 5-HT2A receptor agonist, 5-chloro-αMT may producepsychedelic effects.[1][3] Indeed, its close analogue 5-fluoro-αMT produces a stronghead-twitch response in rats,[4] a property which is highly correlated with psychedelic effects in humans,[3][5] and αMT is well-established as a psychedelic drug in humans.[6]
^abYamamoto T, Ueki S (January 1981). "The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs".Pharmacol. Biochem. Behav.14 (1):89–95.doi:10.1016/0091-3057(81)90108-8.PMID6258178.S2CID45561708.
^Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice".Psychopharmacologia.11 (1):65–78.doi:10.1007/bf00401509.PMID5302272.S2CID3148623.
^Kinemuchi H, Arai Y (October 1986). "Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine".Res. Commun. Chem. Pathol. Pharmacol.54 (1):125–8.doi:10.1016/0028-3908(91)90057-i.PMID3797802.S2CID34761939.
^Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F (August 2000). "Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat".Progress in Neuro-psychopharmacology & Biological Psychiatry.24 (6):955–77.doi:10.1016/S0278-5846(00)00113-5.PMID11041537.S2CID24347904.
^Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)".European Journal of Pharmacology.200 (1):187–90.doi:10.1016/0014-2999(91)90686-K.PMID1722753.
^Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN978-0-85608-011-1.OCLC2176880.OL4850660M.[...] 5-chloro-, but not 6-chloro-, derivatives of α-methyl- and α-ethyl-tryptamine produced behavioural changes in animals (Whittle and Young, 1963); [...]
^Whittle BA, Young EH (July 1963). "The Synthesis and Pharmacological Activity of Some Chloro-α-alkyltryptamines".J Med Chem.6 (4):378–380.doi:10.1021/jm00340a009.PMID14184890.The synthesis of eight new monochloro analogs of a-methyl- and a-ethyltryptamines are described. These compounds were prepared by condensations of 4-, 5-, 6-, and 7-chloroindole-3-aldehydes with either nitroethane or nitropropane and subsequent reduction of the condensation products with lithium aluminum hydride. The tryptamines have been found to possess stimulant and anticonvulsant properties in rodents and to produce behavioral changes in cats. [...]
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