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Chemical Compound Review

Orlaam     [(3S,6S)-6-dimethylamino-4,4- diphenyl...

Synonyms: LAAM, Levomethadyl, CHEMBL1514, SureCN93805, CHEBI:6441, ...
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Disease relevance of levo-alpha-Acetylmethadol


Psychiatry related information on levo-alpha-Acetylmethadol


High impact information on levo-alpha-Acetylmethadol


Chemical compound and disease context of levo-alpha-Acetylmethadol


Biological context of levo-alpha-Acetylmethadol


Anatomical context of levo-alpha-Acetylmethadol


Associations of levo-alpha-Acetylmethadol with other chemical compounds


Gene context of levo-alpha-Acetylmethadol

  • The ratio [dinor-LAAM/(nor-LAAM plus dinor-LAAM)] with microsomes and CYP3A4 decreased with increasing LAAM concentration, suggesting most dinor-LAAM is formed from released nor-LAAM that subsequently reassociates with CYP3A4 [23].
  • Of the cDNA-expressed isoforms examined, CYP2B6 and 3A4 had the highest activity toward LAAM and nor-LAAM at both low (2 microM) and high (250 microM) substrate concentrations [23].
  • 3. Using patch clamp electrophysiology, we found that l-alpha-acetylmethadol inhibited HERG channel currents in a voltage-dependent manner displaying an IC(50) value of 3 microM [31].
  • The major active metabolite of l-alpha-acetylmethadol, noracetylmethadol, inhibited HERG with an estimated IC(50) values of 12 microM. l-alpha-acetylmethadol had little or no effect on Kv4.3 or KvLQT1/minK K(+) channel currents at concentration up to 10 microM [31].
  • Hepatic and intestinal microsomal N-demethylation in vitro is catalysed mainly by cytochrome P450 (CYP) 3A4; however, the role of CYP3A in LAAM disposition in humans in vivo is unknown [2].

Analytical, diagnostic and therapeutic context of levo-alpha-Acetylmethadol


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  5. Relative potency of levo-alpha-acetylmethadol and methadone in humans under acute dosing conditions. Eissenberg, T., Stitzer, M.L., Bigelow, G.E., Buchhalter, A.R., Walsh, S.L. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
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  10. Dose-response analysis of opioid cross-tolerance and withdrawal suppression during LAAM maintenance. Houtsmuller, E.J., Walsh, S.L., Schuh, K.J., Johnson, R.E., Stitzer, M.L., Bigelow, G.E. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
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  12. Acute effects of ethanol on hepatic uptake and distribution of narcotics in the isolated perfused rabbit liver. Kreek, M.J., Rothschild, M.A., Oratz, M., Mongelli, J., Handley, A.C. Hepatology (1981) [Pubmed]
  13. Plasma l-alpha-Acetylmethadol (LAAM) after acute and chronic administration. Henderson, G.L., Wilson, B.K., Lau, D.H. Clin. Pharmacol. Ther. (1977) [Pubmed]
  14. The naloxone test for opiate dependence. Judson, B.A., Himmelberger, D.U., Goldstein, A. Clin. Pharmacol. Ther. (1980) [Pubmed]
  15. Toxicological evaluation of mu-agonists. Part I: Assessment of toxicity following 30 days of repeated oral dosing of male and female rats with levo-alpha-acetylmethadol HCl (LAAM). Borzelleca, J.F., Egle, J.L., Harris, L.S., Johnson, D.N., Terrill, J.B., Belleville, J.A. Journal of applied toxicology : JAT. (1994) [Pubmed]
  16. Clinical toxicology of drugs used in the treatment of opiate dependency. Fraser, A.D. Clin. Lab. Med. (1990) [Pubmed]
  17. Integration of research in pharmacotherapy for addictive disease: where are we? Where are we going? Ling, W., Shoptaw, S. Journal of addictive diseases : the official journal of the ASAM, American Society of Addiction Medicine. (1997) [Pubmed]
  18. Enterohepatic circulation of l-alpha-acetylmethadol in the rat. Roerig, D.L., Hasegawa, A.T., Wang, R.I. J. Pharmacol. Exp. Ther. (1980) [Pubmed]
  19. Intravenous and oral l-alpha-acetylmethadol: pharmacodynamics and pharmacokinetics in humans. Walsh, S.L., Johnson, R.E., Cone, E.J., Bigelow, G.E. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  20. Metabolism of methadone and levo-alpha-acetylmethadol (LAAM) by human intestinal cytochrome P450 3A4 (CYP3A4): potential contribution of intestinal metabolism to presystemic clearance and bioactivation. Oda, Y., Kharasch, E.D. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  21. Transfer of L-alpha-acetylmethadol (LAAM) and L-alpha-acetyl-N-normethadol (norLAAM) by the perfused human placental lobule. Nanovskaya, T.N., Deshmukh, S.V., Miles, R., Burmaster, S., Ahmed, M.S. J. Pharmacol. Exp. Ther. (2003) [Pubmed]
  22. Physiological disposition and biotransformation of l-alpha-[2-3H]acetylmethadol (LAAM) in acutely and chronically treated monkeys. Misra, A.L., Mulé, S.J., Bloch, R., Bates, T.R. J. Pharmacol. Exp. Ther. (1978) [Pubmed]
  23. Metabolism of levo-alpha-Acetylmethadol (LAAM) by human liver cytochrome P450: involvement of CYP3A4 characterized by atypical kinetics with two binding sites. Oda, Y., Kharasch, E.D. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  24. Prenatal opiate exposure attenuates LPS-induced fever in adult rats: Role of interleukin-1beta. Hamilton, K.L., Franklin, L.M., Roy, S., Schrott, L.M. Brain Res. (2007) [Pubmed]
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  26. Peripheral sympatholytic effects of 1-alpha-acetylmethadol. Stickney, J.L., Eikenburg, D.C. J. Cardiovasc. Pharmacol. (1981) [Pubmed]
  27. Sex and age dependence of the "selective" induction of rat hepatic microsomal epoxide hydratase following trans-stilbene oxide, l-alpha-acetylmethadol, or phenobarbital treatment. Gontovnick, L.S., Bellward, G.D. Biochem. Pharmacol. (1980) [Pubmed]
  28. Hepatic glutathione and hepatotoxicity: effects of cytochrome P-450 complexing compounds SKF 525-A, L-alpha acetylmethadol (LAAM), norLAAM, and piperonyl butoxide. James, R.C., Harbison, R.D. Biochem. Pharmacol. (1982) [Pubmed]
  29. Efficacy of dose and contingency management procedures in LAAM-maintained cocaine-dependent patients. Oliveto, A., Poling, J., Sevarino, K.A., Gonsai, K.R., McCance-Katz, E.F., Stine, S.M., Kosten, T.R. Drug and alcohol dependence. (2005) [Pubmed]
  30. Development of cellular tolerance to lethality and analgesia concurrent with physical dependence following repeated oral administration of LAAM. Masten, L.W. Drug and alcohol dependence. (1979) [Pubmed]
  31. Interactions of the narcotic l-alpha-acetylmethadol with human cardiac K+ channels. Kang, J., Chen, X.L., Wang, H., Rampe, D. Eur. J. Pharmacol. (2003) [Pubmed]
  32. Opiate withdrawal in utero increases neonatal morbidity in the rat. Lichtblau, L., Sparber, S.B. Science (1981) [Pubmed]
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  34. Effects of levo-alpha-acetylmethadol (LAAM) on morphine self-administration in the rat. Lukas, S.E., Moreton, J.E., Khazan, N. Psychopharmacology (Berl.) (1981) [Pubmed]
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