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Chemical Compound Review

DMAc     N,N-dimethylethanamide

Synonyms: Hallucinogen, HSDB 74, CHEMBL11873, NSC-3138, CCRIS 4623, ...
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Disease relevance of Dimethyl acetamide


Psychiatry related information on Dimethyl acetamide

  • In general, the evidence suggests that the prevalence of substance abuse in schizophrenia is comparable to that in the general population, with the possible exceptions of stimulant and hallucinogen abuse, which may be greater in patients with schizophrenia [6].
  • CONCLUSIONS: While the prevailing view was that the activation of 5-HT(2) receptors is solely responsible for hallucinogenic drug effects, these results support a role for 5-HT(1A) receptors in the effects of the indoleamine hallucinogen 5-MeO-DMT on locomotor activity and PPI in rats [7].
  • Among them, 83 had a diagnosis of alcohol dependence, 41 of heroin dependence and the remaining 17 cases of sedative, glue or hallucinogen dependence [8].
  • Psychometric assessment of the Hallucinogen Rating Scale [9].
  • Two variables were predictive of sexual risk-taking: higher level of hallucinogen use and sexual relationship with an IDU [10].

High impact information on Dimethyl acetamide


Chemical compound and disease context of Dimethyl acetamide


Biological context of Dimethyl acetamide


Anatomical context of Dimethyl acetamide

  • Number of surviving spermatozoa diminished progressively with increasing DMA concentrations in all species [26].
  • A major role for thalamocortical afferents in serotonergic hallucinogen receptor function in the rat neocortex [27].
  • CONCLUSION: It is discussed that ayahuasca-induced survival of binocular rivalry at high DSA rates may be related to slow visual processing and increased mean dominance periods may result from hallucinogen-induced alteration of gamma oscillations in the visual pathways [28].
  • Consistent with a partial agonist action, LSD and DOI blocked the 5-HT excitation of piriform cortical interneurons only at the higher hallucinogen concentrations tested [29].
  • The effects of the hallucinogen, harmaline (HME), and its congeners on human red blood cell (RBC) transport were studied [30].

Associations of Dimethyl acetamide with other chemical compounds


Gene context of Dimethyl acetamide

  • For example, 7b substituted for LSD in the drug discrimination assay with an ED50 of 61 nmol/kg and had Kj values in the nanomolar to subnanomolar range for the displacement of radioligand from rat and human 5-HT2 receptors, making it one of the most potent hallucinogen-like phenylalkylamine derivatives reported to date [36].
  • 5-MeO-DIPT is thus effective in two rodent models of 5-HT2 agonist activity, and has affinity at receptors relevant to hallucinogen effects [37].
  • In the present work, the effect of DMF and of the structurally related N,N-dimethylacetamide (DMAc) on the activating enzyme and the nature of the reactive species involved in the mechanism of P450 inactivation by the two chemicals were investigated in vitro [38].
  • The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors [39].
  • Evidence for a common biological basis of the Absorption trait, hallucinogen effects, and positive symptoms: epistasis between 5-HT2a and COMT polymorphisms [40].

Analytical, diagnostic and therapeutic context of Dimethyl acetamide


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  11. A new class of inhibitors of lymphocyte mitogenesis: agents that induce erythroid differentiation in Friend leukemia cells. Novogrodsky, A., Rubin, A.L., Stenzel, K.H. J. Immunol. (1980) [Pubmed]
  12. Highly stereoselective asymmetric pummerer reactions that incorporate intermolecular and intramolecular nonbonded S...O interactions. Nagao, Y., Miyamoto, S., Miyamoto, M., Takeshige, H., Hayashi, K., Sano, S., Shiro, M., Yamaguchi, K., Sei, Y. J. Am. Chem. Soc. (2006) [Pubmed]
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  14. Acid-base chemistry of a carbenium ion in a zeolite under equilibrium conditions: verification of a theoretical explanation of carbenium ion stability. Song, W., Nicholas, J.B., Haw, J.F. J. Am. Chem. Soc. (2001) [Pubmed]
  15. 4-[125I]iodo-(2,5-dimethoxy)phenylisopropylamine and [3H]ketanserin labeling of 5-hydroxytryptamine2 (5HT2) receptors in mammalian cells transfected with a rat 5HT2 cDNA: evidence for multiple states and not multiple 5HT2 receptor subtypes. Teitler, M., Leonhardt, S., Weisberg, E.L., Hoffman, B.J. Mol. Pharmacol. (1990) [Pubmed]
  16. Evidence that 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane-induced hypophagia and hyperthermia in rats is mediated by serotonin-2A receptors. Aulakh, C.S., Mazzola-Pomietto, P., Wozniak, K.M., Hill, J.L., Murphy, D.L. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  17. Posthallucinogen-like visual illusions (palinopsia) with risperidone in a patient without previous hallucinogen exposure: possible relation to serotonin 5HT2a receptor blockade. Lauterbach, E.C., Abdelhamid, A., Annandale, J.B. Pharmacopsychiatry (2000) [Pubmed]
  18. Illicit drug use and anxiety disorders: findings from two community surveys. Sareen, J., Chartier, M., Paulus, M.P., Stein, M.B. Psychiatry research. (2006) [Pubmed]
  19. Acute and subchronic toxicity of dimethylformamide and dimethylacetamide following various routes of administration. Kennedy, G.L., Sherman, H. Drug and chemical toxicology. (1986) [Pubmed]
  20. Acute safety and pharmacokinetics of intravenous busulfan when used with oral busulfan and cyclophosphamide as pretransplantation conditioning therapy: a phase I study. Andersson, B.S., Madden, T., Tran, H.T., Hu, W.W., Blume, K.G., Chow, D.S., Champlin, R.E., Vaughan, W.P. Biol. Blood Marrow Transplant. (2000) [Pubmed]
  21. Interaction of mescaline with phenothiazines: effect on behavior, body temperature, and tissue levels of hallucinogen in mice. Shah, N.S., Jacobs, J.R., Jones, J.T., Hedden, M.P. Biol. Psychiatry (1975) [Pubmed]
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  23. Preclinical toxicology and pharmacology of dimethylacetamide, with clinical notes. Kim, S.N. Drug Metab. Rev. (1988) [Pubmed]
  24. HIV-related risk behavior among Hispanic immigrant men in a population-based household survey in low-income neighborhoods of northern California. Levy, V., Page-Shafer, K., Evans, J., Ruiz, J., Morrow, S., Reardon, J., Lynch, M., Raymond, H.F., Klausner, J.D., Facer, M., Molitor, F., Allen, B., Ajufo, B.G., Ferrero, D., Sanford, G.B., McFarland, W. Sexually transmitted diseases. (2005) [Pubmed]
  25. Microsomal metabolism of N,N-diethylacetamide and N,N-dimethylacetamide and their effects on drug-metabolizing enzymes of rat liver. Silvia, M., Vincenzo, L., Arturo, M., Giovanni, G.P. Biochem. Pharmacol. (1994) [Pubmed]
  26. Species variation in osmotic, cryoprotectant, and cooling rate tolerance in poultry, eagle, and peregrine falcon spermatozoa. Blanco, J.M., Gee, G., Wildt, D.E., Donoghue, A.M. Biol. Reprod. (2000) [Pubmed]
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  28. Effects of ayahuasca on binocular rivalry with dichoptic stimulus alternation. Frecska, E., White, K.D., Luna, L.E. Psychopharmacology (Berl.) (2004) [Pubmed]
  29. LSD and the phenethylamine hallucinogen DOI are potent partial agonists at 5-HT2A receptors on interneurons in rat piriform cortex. Marek, G.J., Aghajanian, G.K. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  30. The effects of harmaline on sodium transport in human erythrocytes: evidence in favor of action at interior sodium-sensitive sites. Dunn, M.J., Hunt, W. J. Pharmacol. Exp. Ther. (1975) [Pubmed]
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  36. Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups. Monte, A.P., Marona-Lewicka, D., Parker, M.A., Wainscott, D.B., Nelson, D.L., Nichols, D.E. J. Med. Chem. (1996) [Pubmed]
  37. Hallucinogen-like actions of 5-methoxy-N,N-diisopropyltryptamine in mice and rats. Fantegrossi, W.E., Harrington, A.W., Kiessel, C.L., Eckler, J.R., Rabin, R.A., Winter, J.C., Coop, A., Rice, K.C., Woods, J.H. Pharmacol. Biochem. Behav. (2006) [Pubmed]
  38. Inactivation of rat liver cytochrome P450 (P450) by N,N-dimethylformamide and N,N-dimethylacetamide. Tolando, R., Zanovello, A., Ferrara, R., Iley, J.N., Manno, M. Toxicol. Lett. (2001) [Pubmed]
  39. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Winter, J.C., Filipink, R.A., Timineri, D., Helsley, S.E., Rabin, R.A. Pharmacol. Biochem. Behav. (2000) [Pubmed]
  40. Evidence for a common biological basis of the Absorption trait, hallucinogen effects, and positive symptoms: epistasis between 5-HT2a and COMT polymorphisms. Ott, U., Reuter, M., Hennig, J., Vaitl, D. Am. J. Med. Genet. B Neuropsychiatr. Genet. (2005) [Pubmed]
  41. Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue. Nichols, D.E., Woodard, R., Hathaway, B.A., Lowy, M.T., Yom, K.W. J. Med. Chem. (1979) [Pubmed]
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