# 2C-H

2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug of the phenethylamine and 2C (4-substituted 2,5-dimethoxyphenethylamine) families. It is the parent compound of the 2C drugs.

## Use and effects

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.

## Pharmacology

2C-H activities :
| Target | Affinity (K$_i$, nM) |
| 5-HT$_{1A}$ | 70 |
| 5-HT$_{1B}$–5-HT$_{1F}$ | ND |
| 5-HT$_{2A}$ | 1,600–3,000 (K$_i$) 2,408–>10,000 (EC$_{50}$Tooltip half-maximal effective concentration) 17,800 (IC$_{50}$Tooltip half-maximal inhibitory concentration) 0–78% (E$_{max}$Tooltip maximal efficacy) |
| 5-HT$_{2B}$ | 6,200 (EC$_{50}$) 46% (E$_{max}$) |
| 5-HT$_{2C}$ | 4,100–5,520 (K$_i$) 1,175–3,967 (EC$_{50}$) 76% (E$_{max}$) |
| 5-HT$_3$–5-HT$_7$ | ND |
| α$_{1A}$ | 7,900 (K$_i$) 11,000 (EC$_{50}$) |
| α$_{1B}$, α$_{1D}$ | ND |
| α$_{2A}$ | 1,000 |
| α$_{2B}$, α$_{2C}$ | ND |
| β$_1$–β$_3$ | ND |
| D$_1$ | >14,000 |
| D$_2$ | 9,000 |
| D$_3$ | >17,000 |
| D$_4$, D$_5$ | ND |
| H$_1$ | >25,000 |
| TAAR1Tooltip Trace amine-associated receptor 1 | 11,000 (K$_i$) (mouse) 900 (K$_i$) (rat) 7,500 (EC$_{50}$) (mouse) 1,500 (EC$_{50}$) (rat) 2,010–6,500 (EC$_{50}$) (human) 56% (E$_{max}$) (mouse) 80% (E$_{max}$) (rat) 53–69% (E$_{max}$) (human) |
| SERTTooltip Serotonin transporter | >30,000 (K$_i$) 311,000 (IC$_{50}$) ND (EC$_{50}$) |
| NETTooltip Norepinephrine transporter | >30,000 (K$_i$) 125,000 (IC$_{50}$) ND (EC$_{50}$) |
| DATTooltip Dopamine transporter | >30,000 (K$_i$) 857,000 (IC$_{50}$) ND (EC$_{50}$) |
| MAO-ATooltip Monoamine oxidase A | ND (IC$_{50}$) |
| MAO-BTooltip Monoamine oxidase B | 1,700 (IC$_{50}$) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: ||
2C-H acts as a partial agonist of the serotonin 5-HT$_{2A}$, 5-HT$_{2B}$, and 5-HT$_{2C}$ receptors, albeit with far lower potency than other 2C drugs. It also shows affinity for the serotonin 5-HT$_{1A}$ receptor, higher than that of any other 2C drug. The drug exhibits agonist activity in vitro at the human trace amine associated receptor 1 (TAAR1).
2C-H produces visual and auditory changes in rodents, but is much less potent than other 2C drugs. It also produces hypolocomotion at high doses similarly to other psychedelics, but failed to affect prepulse inhibition in contrast to other psychedelics. The drug shows highly potent and fully efficacious anti-inflammatory effects.

## Chemistry

2C-H is used as a precursor in the synthesis of other phenethylamines such as 2C-B, 2C-I, and 2C-N.
The N-methyl derivative of 2C-H, N-methyl-2C-H, has reduced activational potency and efficacy at the serotonin 5-HT$_{2A}$ receptor compared to 2C-H.

## History

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

## 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.