5-MeO-DALT

5-MeO-DALT (N,N-diallyl-5-methoxytryptamine; CAS 928822-98-4) is a synthetic substituted tryptamine first synthesized and disclosed by Alexander Shulgin in May 2004 and subsequently disseminated through online research chemical markets. The compound is a structural analog of N,N-diallyltryptamine (DALT) bearing a 5-methoxy substituent on the indole ring, placing it in the broader family of 5-methoxy-substituted tryptamines alongside 5-MeO-DMT, 5-MeO-DiPT, and 5-MeO-MiPT, while the N,N-diallyl substitution pattern distinguishes it from all clinically investigated members of this series. Receptor binding profiling conducted by Cozzi and Daley (2016) and extended by Klein, Cozzi, Daley, Brandt, and Halberstadt (2018) across panels of 45 cloned human receptors and transporters has established that 5-MeO-DALT exhibits nanomolar affinity at the 5-HT1A receptor (Ki approximately 19 nM), the 5-HT2B receptor (Ki approximately 59 nM), the 5-HT7 receptor (Ki approximately 90 nM), and the 5-HT1D receptor (Ki approximately 107 nM), with additional sub-micromolar binding at the 5-HT6, 5-HT2A, alpha-2A adrenergic, sigma-1, and sigma-2 receptors. Functional assays demonstrate full agonist activity at the 5-HT1A receptor (Emax 99 to 102 percent of reference) and partial to full agonist activity at the 5-HT2A receptor (Emax 91 to 114 percent), the latter consistent with the hallucinogenic behavioral profile observed in the mouse head-twitch response assay (ED50 2.25 mg/kg). The compound additionally exhibits measurable affinity at the kappa-opioid receptor and weak activity at dopamine and serotonin transporters, producing a polypharmacological fingerprint that is broader than that of classical N,N-dimethyltryptamine analogs and that may account for the subjective profile described in self-experimentation reports as qualitatively distinct from other 5-methoxytryptamines. Pharmacokinetic characterization is limited to forensic and case-report data. Oral onset is rapid (less than 15 minutes), duration is short (2 to 4 hours), and the metabolic disposition involves CYP1A2, CYP2C19, CYP2D6, and CYP3A4-mediated N-dealkylation, hydroxylation (both aromatic and aliphatic), O-demethylation, and glucuronide conjugation, as characterized in the Michely et al. (2015) in vitro and rat in vivo metabolism study. A clinical case report documented a serum concentration of 7 ng/mL at 8 hours after ingestion of approximately 97.5 mg, with complete clinical recovery by 12 hours, consistent with a short elimination half-life. The compound has no therapeutic indication, no approved clinical use, and no registration in any jurisdiction. It is classified as a novel psychoactive substance and is controlled in Japan (2007), Sweden (2012), the United Kingdom (2015, Class A), China (2015), Singapore (2015), and in the United States states of Florida and Louisiana (Schedule I), but is not scheduled at the United States federal level. The published toxicological literature comprises a small number of case reports documenting loss of consciousness, visual hallucinations, delirium, rhabdomyolysis, and one reported fatality. No systematic preclinical safety pharmacology, reproductive toxicology, or genotoxicity studies have been published. This monograph documents the chemistry, synthesis, receptor pharmacology, metabolism, behavioral pharmacology, reported adverse events, legal status, and comparative positioning of 5-MeO-DALT against five structurally or pharmacologically related tryptamines across five assessment standards.