2,4,5-Trihydroxyamphetamine

2,4,5-trihydroxyamphetamine.svg skin-invert-image 200px 5-(2-Aminopropyl)benzene-1,2,4-triol THA; THA-2; α-Methyl-6-hydroxydopamine; α-Me-6-OHDA; 2,4,5-TDM-TMA-2; 2,4,5-Tridesmethyl-TMA-2 136706-33-7 28225 126234 112205 C6JI2489W2 CC(N)CC1=C(O)C=C(O)C(O)=C1 1S/C9H13NO3/c1-5(10)2-6-3-8(12)9(13)4-7(6)11/h3-5,11-13H,2,10H2,1H3 FWNNQQDQXAMXMK-UHFFFAOYSA-N 9 13 1 3 2,4,5-Trihydroxyamphetamine (THA or THA-2), also known as α-methyl-6-hydroxydopamine (α-Me-6-OHDA) or as 2,4,5-TDM-TMA-2, is a neurotoxin and a metabolite of MDMA related to 6-hydroxydopamine. Iversen LL, Iversen SD, Snyder SH Shulgin Alexander T. Stimulants Psychotomimetic Drugs: Structure-Activity Relationships Springer US Boston, MA 1978 978-1-4757-0512-6 10.1007/978-1-4757-0510-2_6 243–333 https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_6 https://books.google.com/books?id=h0_uBwAAQBAJ&pg=PA261 There is a theoretical interest in TMA-2 stemming from the recognition of 6-hydroxydopamine (38) as a potent disrupting agent within the adrenergic nervous system. The two compounds have an identical oxygen substitution, and TMA-2 (34) has been shown to be partially demethylated in vivo (Mitoma, 1970; Sargent et al., 1976). The totally demethylated product from TMA-2 is 2,4,5-trihydroxyphenylisopropylamine (39), which has been explored as an antihypertensive agent, but which exhibits no mental effects at dosages as high as 200 mg (Stone, 1963).Shulgin Alexander T. Profiles of Psychedelic Drugs: 1. DMT & 2. TMA-2 Journal of Psychedelic Drugs 8 2 1976 0022-393X 10.1080/02791072.1976.10471846 167–169 https://bitnest.netfirms.com/external/10.1080/02791072.1976.10471846 Theoretical interest in TMA-2 stems from the recognition of 6-hydroxy dopamine as an extremely potent disrupter of the adrenergic nervous system. TMA-2 is structurally related with an identical oxygenation pattern, and has been shown to be partially demethylated in vivo. The end product, 2,4,5-trihydroxyamphetamine, has been studied clinically as an antihypertensive, but has not been reported to produce sensory or perceptual changes in humans even at dosages of 200 mg. The metabolism and fate of TMA-2 in humans is unknown. It comes from the ring hydroxylation of 3,4-methylenedioxyamphetamine (MDA). The drug may also be a metabolite of 2,4,5-trimethoxyamphetamine (2,4,5-TMA; TMA-2) via O-demethylation. In one study, it was shown to reduce hippocampal tryptophan hydroxylase activity by 54% after short-term treatment. Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxylase activity. 8496826 265 2 May 1993 J Pharmacol Exp Ther 813–8 Elayan I. Gibb J. W. Hanson G. R. Lim H. K. Foltz R. L. Johnson M. 10.1016/S0022-3565(25)38208-X In another study, it was shown to significantly reduce striatal tyrosine hydroxylase activity. J Pharmacol Exp Ther 1993 265 2 813–818 Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxyls activity Elayan I, Gibb JW, Hanson GR, Lim HK, Foltz RL, Johnson M 10.1016/S0022-3565(25)38208-X 8496826 THA was studied clinically as an antihypertensive agent but was never marketed. The drug did not produce hallucinogenic effects in humans at doses of up to 200mg orally.Stone, C. A., 1963, Composition hypotensive et son utilisation, Brev. Beige, #633,963. See also Monoaminergic neurotoxin 2,4,5-Trihydroxymethamphetamine (THMA) 3,4-Dihydroxyamphetamine (HHA; α-methyldopamine) 3,4-Dihydroxymethamphetamine (HHMA; α-methylepinine) 4-Hydroxy-3-methoxyamphetamine (HMA) 4-Hydroxy-3-methoxymethamphetamine (HMMA) 2,5-DDM-DOM (2,5-dihydroxy-4-methylamphetamine) References External links THA-2 - Isomer Design Category:Human pathological metabolites Category:Monoaminergic neurotoxins Category:Psychedelic drug metabolites Category:Substituted amphetamines