O-DSMT (O-Desmethyltramadol)

O-Desmethyltramadol is the active metabolite of tramadol for mu-opioid receptor research. Purity ≥98% (HPLC). For research purposes only.

Product Name: O-DSMT (O-Desmethyltramadol) Synonyms: Desmetramadol; 3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenol; O-Desmethyl tramadol

General Description: O-DSMT is formally described as 3-[2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol. It is a synthetic, psychoactive molecule belonging to the cyclohexanol class. O-DSMT is the primary biologically active metabolite of the widely prescribed atypical opioid analgesic tramadol. In the body, tramadol is metabolized into O-DSMT by the hepatic enzyme CYP2D6. In recent years, O-DSMT has also emerged independently on the illicit designer drug market as a novel psychoactive substance (NPS).

In analytical, clinical, and forensic toxicology, O-DSMT is utilized as a fundamental reference standard. It is essential for the calibration of analytical instrumentation (such as LC-MS/MS, GC-MS, and HPLC) and the development of screening methodologies to identify and quantify the substance in seized materials, adulterated illicit street drugs, or biological matrices (e.g., whole blood, plasma, urine), both to detect illicit use and to monitor tramadol metabolism.

Technical Information (Hydrochloride Salt):

• CAS Number: 144514-41-4 (Hydrochloride) / 73986-53-5 (Freebase)
• Molecular Formula: C₁₅H₂₃NO₂ • HCl
• Formula Weight: 285.8 g/mol (Hydrochloride) / 249.35 g/mol (Freebase)
• SMILES: CN(C)CC1(CCCCC1O)C2=CC(=CC=C2)O.Cl
• InChI Key: HKSZLNNCZMWEAE-UHFFFAOYSA-N (Freebase)
• Formulation: Typically supplied as a neat white crystalline solid or as a certified reference material solution (e.g., 1 mg/mL or 100 µg/mL in methanol).

O-DSMT (O-Desmethyltramadol) Biological Action: O-DSMT acts as a high-affinity agonist at the μ-opioid receptor (MOR). Notably, its affinity and efficacy at the MOR are significantly higher than those of its parent compound, tramadol. Consequently, O-DSMT is responsible for the vast majority of the classical opioid analgesic effects observed following tramadol administration. Unlike tramadol, which acts as a prominent serotonin-norepinephrine reuptake inhibitor (SNRI), O-DSMT retains primarily norepinephrine reuptake inhibition (NRI) properties and has negligible affinity for the serotonin transporter. At supratherapeutic doses, O-DSMT carries a significant risk of classical opioid toxidromes, including profound respiratory depression, sedation, miosis, and euphoria.

Regulatory and Safety Information:

• Intended Use: This product is intended strictly for use as an analytical reference standard for forensic, toxicological, and academic research purposes.
• Warning: This product is a potent opioid and carries a severe risk of physiological dependence and fatal overdose. It is not for human or veterinary use outside of strictly approved clinical or laboratory environments.
• Legal Status: The regulatory status of O-DSMT varies globally and is subject to change as its prevalence as an NPS increases. In the United States, tramadol is a Schedule IV Controlled Substance, and while O-DSMT has historically occupied a grey area, it is increasingly being placed under independent scheduling by various state legislatures and international regulatory bodies. Procurement may require relevant local or institutional licenses. Handling should only occur within professional laboratory environments using appropriate Personal Protective Equipment (PPE) such as safety glasses, chemical-resistant gloves, and a laboratory coat to prevent accidental exposure.