# 2C-D

2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.
Not much information is known about the toxicity of 2C-D, as no major studies have been conducted. According to Shulgin, the effects of 2C-D typically last for 4–6 hours. Shulgin himself referred to this substance as a “pharmacological tofu,” meaning that when mixed with other substances, it can extend or potentiate their effects without coloring the experience too much, in a manner similar to how tofu absorbs the flavors of sauces or spices it is cooked with. Hanscarl Leuner, working in Germany, explored the use of 2C-D under the name LE-25 in psychotherapeutic research.

## Interactions

2C-D is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-D. This may result in overdose and serious toxicity.

## Pharmacology

2C-D activities :
| Target | Affinity (K$_i$, nM) |
| 5-HT$_{1A}$ | 440–1,630 (K$_i$) >10,000 (EC$_{50}$Tooltip half-maximal effective concentration) <25% (E$_{max}$Tooltip maximal efficacy) |
| 5-HT$_{1B}$–5-HT$_{1F}$ | ND |
| 5-HT$_{2A}$ | 23.9–32.4 (K$_i$) 43.5–8,130 (EC$_{50}$) 6–93% (E$_{max}$) |
| 5-HT$_{2B}$ | ND (K$_i$) 230 (EC$_{50}$) 77% (E$_{max}$) |
| 5-HT$_{2C}$ | 12.7–150 (K$_i$) 71.1–18,600 (EC$_{50}$) 48–100% (E$_{max}$) |
| 5-HT$_3$–5-HT$_7$ | ND |
| α$_{1A}$ | 12,000 |
| α$_{1B}$, α$_{1D}$ | ND |
| α$_{2A}$ | 290 |
| α$_{2B}$, α$_{2C}$ | ND |
| β$_1$–β$_3$ | ND |
| D$_1$ | 24,000 |
| D$_2$ | 7,100 |
| D$_3$ | >17,000 |
| D$_4$ | ND |
| D$_5$ | ND |
| H$_1$ | >25,000 |
| H$_2$–H$_4$ | ND |
| M$_1$–M$_5$ | ND |
| I$_1$ | ND |
| σ$_1$, σ$_2$ | ND |
| TAAR1Tooltip Trace amine-associated receptor 1 | 3,500 (K$_i$) (mouse) 150 (K$_i$) (rat) 2,000 (EC$_{50}$) (mouse) 490 (EC$_{50}$) (rat) >10,000 (EC$_{50}$) (human) 61% (E$_{max}$) (mouse) 55% (E$_{max}$) (rat) |
| SERTTooltip Serotonin transporter | 31,000 (K$_i$) 77,000 (IC$_{50}$Tooltip half-maximal inhibitory concentration) IA (EC$_{50}$) |
| NETTooltip Norepinephrine transporter | >30,000 (K$_i$) 45,000 (IC$_{50}$) IA (EC$_{50}$) |
| DATTooltip Dopamine transporter | >30,000 (K$_i$) 626,000 (IC$_{50}$) IA (EC$_{50}$) |
| MAO-ATooltip Monoamine oxidase A | ND (IC$_{50}$) |
| MAO-BTooltip Monoamine oxidase B | 24,000 (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-D is a partial agonist of the serotonin 5-HT$_{2A}$, 5-HT$_{2B}$, and 5-HT$_{2C}$ receptors.

## Legal status
### China

As of October 2015 2C-D is a controlled substance in China.

### Canada

As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.

### Denmark

2C-D is added to the list of Schedule B controlled substances.

### Finland

Listed in the government decree on psychoactive substances banned from the consumer market.

### Germany

2C-D is an Anlage I controlled drug.

### Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut [sv] classified 2C-D as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor [sv] (Act on the Prohibition of Certain Goods Dangerous to Health) as of Mar 1, 2005, in their regulation SFS 2005:26 listed as "2,5-dimetoxi-4-metylfenetylamin (2C-D)", making it illegal to sell or possess.

### United States

2C-D became a Schedule I Controlled Substance in the United States as of July 9, 2012, with the signing of Food and Drug Administration Safety and Innovation Act. On a state level, both Oklahoma and Pennsylvania list 2C-D under schedule I.