2,4,5-Trihydroxyamphetamine
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| Preferred IUPAC name
5-(2-Aminopropyl)benzene-1,2,4-triol | |
| Other names
THA; THA-2; α-Methyl-6-hydroxydopamine; α-Me-6-OHDA; 2,4,5-TDM-TMA-2; 2,4,5-Tridesmethyl-TMA-2
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3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C9H13NO3 | |
| Molar mass | 183.207 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
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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.[1][2] 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.[1][2] In one study, it was shown to reduce hippocampal tryptophan hydroxylase activity by 54% after short-term treatment.[3] In another study, it was shown to significantly reduce striatal tyrosine hydroxylase activity.[4] THA was studied clinically as an antihypertensive agent but was never marketed.[1][2] The drug did not produce hallucinogenic effects in humans at doses of up to 200 mg orally.[1][2][5]
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
- ^ a b c d Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
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).
- ^ a b c d Shulgin, Alexander T. (1976). "Profiles of Psychedelic Drugs: 1. DMT & 2. TMA-2". Journal of Psychedelic Drugs. 8 (2): 167–169. doi:10.1080/02791072.1976.10471846. ISSN 0022-393X.
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.
- ^ Elayan, I.; Gibb, J. W.; Hanson, G. R.; Lim, H. K.; Foltz, R. L.; Johnson, M. (May 1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxylase activity". J Pharmacol Exp Ther. 265 (2): 813–8. doi:10.1016/S0022-3565(25)38208-X. PMID 8496826.
- ^ Elayan I, Gibb JW, Hanson GR, Lim HK, Foltz RL, Johnson M (1993). "Short-term effects of 2,4,5-trihydroxyamphetamine, 2,4,5-trihydroxymethamphetamine and 3,4-dihydroxymethamphetamine on central tryptophan hydroxyls activity". J Pharmacol Exp Ther. 265 (2): 813–818. doi:10.1016/S0022-3565(25)38208-X. PMID 8496826.
- ^ Stone, C. A., 1963, Composition hypotensive et son utilisation, Brev. Beige, #633,963.