PMID- 19874650 OWN - NLM STAT- MEDLINE DCOM- 20100105 LR - 20211028 IS - 1945-2403 (Electronic) IS - 0146-4760 (Print) IS - 0146-4760 (Linking) VI - 33 IP - 8 DP - 2009 Oct TI - Urinary MDMA, MDA, HMMA, and HMA excretion following controlled MDMA administration to humans. PG - 439-46 AB - 3,4-Methylenedioxymethamphetamine (MDMA), or ecstasy, is excreted as unchanged drug, 3,4-methylenedioxyamphetamine (MDA), and free and glucuronidated/sulfated 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) metabolites. The aim of this paper is to describe the pattern and timeframe of excretion of MDMA and its metabolites in urine. Placebo, 1.0 mg/kg, and 1.6 mg/kg oral MDMA doses were administered double-blind to healthy adult MDMA users on a monitored research unit. All urine was collected, aliquots were hydrolyzed, and analytes quantified by gas chromatography-mass spectrometry. Median C(max), T(max), ratios, first and last detection times, and detection rates were determined. Sixteen participants provided 916 urine specimens. After 1.6 mg/kg, median C(max) were 21,470 (MDMA), 2229 (MDA), 20,793 (HMMA), and 876 ng/mL (HMA) at median T(max) of 13.9, 23.0, 9.2 and 23.3 h. In the first 24 h, 30.2-34.3% total urinary excretion occurred. HMMA last detection exceeded MDMA's by more than 33 h after both doses. Identification of HMMA as well as MDMA increased the ability to identify positive specimens but required hydrolysis. These MDMA, MDA, HMMA, and HMA pharmacokinetic data may be useful for interpreting workplace, drug treatment, criminal justice, and military urine drug tests. Measurement of urinary HMMA provides the longest detection of MDMA exposure yet is not included in routine monitoring procedures. FAU - Abraham, Tsadik T AU - Abraham TT AD - Chemistry and Drug Metabolism, Intramural Research Program, National Institute on Drug Abuse, NIH, Baltimore, Maryland 21224, USA. FAU - Barnes, Allan J AU - Barnes AJ FAU - Lowe, Ross H AU - Lowe RH FAU - Kolbrich Spargo, Erin A AU - Kolbrich Spargo EA FAU - Milman, Garry AU - Milman G FAU - Pirnay, Stephane O AU - Pirnay SO FAU - Gorelick, David A AU - Gorelick DA FAU - Goodwin, Robert S AU - Goodwin RS FAU - Huestis, Marilyn A AU - Huestis MA LA - eng GR - ZIA DA000468-07/ImNIH/Intramural NIH HHS/United States PT - Journal Article PT - Research Support, N.I.H., Intramural PL - England TA - J Anal Toxicol JT - Journal of analytical toxicology JID - 7705085 RN - 0 (Hallucinogens) RN - 117652-28-5 (4-hydroxy-3-methoxymethamphetamine) RN - 44RAL3456C (Methamphetamine) RN - 4764-17-4 (3,4-Methylenedioxyamphetamine) RN - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine) RN - ML1I4KK67B (3,4-methylenedioxyethamphetamine) SB - IM MH - 3,4-Methylenedioxyamphetamine/*analogs & derivatives/*urine MH - Adolescent MH - Adult MH - Female MH - Gas Chromatography-Mass Spectrometry MH - *Hallucinogens/pharmacokinetics/urine MH - Humans MH - Male MH - Methamphetamine/*analogs & derivatives/urine MH - *N-Methyl-3,4-methylenedioxyamphetamine/analogs & derivatives/pharmacokinetics/urine MH - Substance Abuse Detection/methods MH - Young Adult PMC - PMC3159864 MID - NIHMS316982 EDAT- 2009/10/31 06:00 MHDA- 2010/01/06 06:00 PMCR- 2011/08/23 CRDT- 2009/10/31 06:00 PHST- 2009/10/31 06:00 [entrez] PHST- 2009/10/31 06:00 [pubmed] PHST- 2010/01/06 06:00 [medline] PHST- 2011/08/23 00:00 [pmc-release] AID - 10.1093/jat/33.8.439 [doi] PST - ppublish SO - J Anal Toxicol. 2009 Oct;33(8):439-46. doi: 10.1093/jat/33.8.439.