2C–H

2C–H, or 2,5-dimethoxyphenethylamine, is a lesser-known substituted phenethylamine of the 2C family.

History

2C–H was first synthesized in 1932 by Johannes S. Buck.

Usage

2C-H is used as a precursor in the synthesis of other substituted phenethylamines. 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 (Phenethylamines i Have Known And Loved), 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

It exhibits agonist activity 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 [3H]mesulergine as a radioligand.