4-HO-MET (Metocin)

4-HO-MET (Metocin)**Product Name:** 4-HO-MET (4-Hydroxy-N-methyl-N-ethyltryptamine) *

*Synonyms:** Metocin; Methylcybin; 4-Hydroxy-MET; 4-OH-MET; 3-[2-(ethylmethylamino)ethyl]-1H-indol-4-ol **General Description:** 4-HO-MET is formally described as 3-[2-(ethyl(methyl)amino)ethyl]-1H-indol-4-ol. It is a synthetic, psychoactive molecule belonging to the tryptamine class. Structurally, 4-HO-MET is the N-ethyl, N-methyl asymmetrical homologue of the naturally occurring psychedelic psilocin (4-HO-DMT), as well as the 4-hydroxy analogue of MET. Initially synthesized and detailed by Alexander Shulgin in his foundational text *TiHKAL* (Tryptamines I Have Known and Loved), it is noted for producing characteristic psychedelic effects that are considered highly comparable to those of psilocybin mushrooms. In analytical, clinical, and forensic toxicology, 4-HO-MET is utilized as a reference standard for the calibration of analytical instruments (such as LC-MS/MS, GC-MS, and NMR) and the development of screening methodologies to identify and quantify illicit designer drugs in seized materials or biological matrices. **Technical Information (Freebase):**
* **CAS Number:** 77872-41-4 *

**Molecular Formula:** C₁₃H₁₈N₂O *

**Formula Weight:** 218.30 g/mol * **SMILES:** CCN(C)CCC1=CNC2=C1C(O)=CC=C2 * **InChI Key:** ORWQBKPSGDRPPA-UHFFFAOYSA-N *

**Formulation:** Typically supplied as a neat crystalline solid (frequently formulated as a fumarate salt to ensure chemical stability, minimize susceptibility to oxidation, and ensure accurate dosing) or as a certified reference material solution (e.g., 1 mg/mL in methanol).

**Biological Action:** 4-HO-MET acts predominantly as a partial agonist at central serotonin receptors, exhibiting substantial binding affinity and efficacy at the 5-HT_2A, 5-HT_1A, and 5-HT_2C subtypes. The potent activation of the 5-HT_2A receptor primarily mediates its psychedelic properties, yielding robust dose-dependent behaviors such as the head-twitch response (HTR) observed in murine models. Furthermore, *in vitro* pharmacological profiles indicate that 4-HO-MET acts as a moderate serotonin transporter (SERT) inhibitor and a weak norepinephrine transporter (NET) inhibitor. **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 not for human or veterinary use.** *

**Legal Status:** The regulatory status of 4-HO-MET varies globally. In the United Kingdom, it is controlled as a Class A substance under the Misuse of Drugs Act. In the United States, 4-HO-MET is not explicitly scheduled at the federal level; however, because it is structurally and pharmacologically homologous to the Schedule I substance psilocin (4-HO-DMT), its manufacturing, distribution, or possession can be prosecuted under the Federal Analogue Act if intended for human consumption. Several individual jurisdictions and European countries have scheduled it independently.