2c-h 2c-h 2c-h (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2c family. 2c-h names preferred iupac name 2-(2,5-dimethoxyphenyl)ethan-1-amine other names 2,5-dimethoxy-phenethylamine identifiers cas number 3600-86-0 (free base) y3166-74-3 (hcl) y 3d model (jsmol) interactive image chembl chembl287047 y chemspider 69096 y echa infocard 100.153.556 pubchem cid 76632 unii 9a8xf4ga0x yp2y262s9pp (hcl) y comptox dashboard (epa) dtxsid80189564 inchi inchi=1s/c10h15no2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7h,5-6,11h2,1-2h3 ykey: wncuvuuejzeatp-uhfffaoysa-n yinchi=1/c10h15no2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7h,5-6,11h2,1-2h3key: wncuvuuejzeatp-uhfffaoyaj smiles o(c1ccc(oc)cc1ccn)c properties chemical formula c10h15no2 molar mass 181.23 g/mol melting point 138 to 139 °c (280 to 282 °f; 411 to 412 k) (hydrochloride) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). n verify (what is yn ?) infobox references history 2c-h was first synthesized in 1932 by johannes s. buck. use 2c-h is used as a precursor in the synthesis of other substituted phenethylamines such as 2c-b, 2c-i, and 2c-n. 2c-h has been found in trace amounts by the dea's south central laboratory in tablets that were suspected of containing mdma. pharmacology there is no record of 2c-h trials in humans, as it would likely be destroyed by monoamine oxidase enzymes before causing any significant psychoactive effects. in the book pihkal, alexander shulgin lists both the dosage and duration of 2c-h effects as unknown. very little data exists about the pharmacological properties, metabolism, and toxicity of 2c-h. research 2c-h exhibits agonist activity in vitro at human trace amine associated receptor 1 expressed in rd-hga16 cho-k1 cells coexpressed with galpha16 protein assessed as internal calcium mobilization. 2c-h was found to be inactive in nci in vivo anticancer drug screens for tumor model l1210 leukemia. it was found to be an active alpha-1 adrenergic receptor agonist in rabbit ear arteries. it has binding affinity towards 5-ht2c and 5-ht2a receptors in rats. it features competitive antagonist activity at 5-ht serotonin receptor in sprague-dawley rat stomachs. it exhibits binding affinity against rat 5-hydroxytryptamine 2c receptors using mesulergine as a radioligand. legal status canada as of october 31, 2016; 2c-h is a controlled substance (schedule iii) in canada. united states as of july 9, 2012, 2c-h is a schedule i controlled substance in the united states, under the synthetic drug abuse prevention act of 2012. 2c-h's dea drug code is 7517.