2C-D
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| _other_data=2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine
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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,<ref name="pmid5412084">Template:Cite journal</ref> and its activity was subsequently investigated in humans by Alexander Shulgin.
Use and effectsEdit
Not much information is known about the toxicity of 2C-D, as no major studies have been conducted. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg.<ref name=Shulgin>2C-D Entry in PiHKAL</ref> Lower doses of 10 mg or less have been explored for microdosing.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> According to Shulgin, the effects of 2C-D typically last for 4–6 hours.<ref name=Shulgin/> 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.Template:Citation needed
InteractionsEdit
2C-D is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-D.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
PharmacologyEdit
| Target | Affinity (Ki, nM) | ||
|---|---|---|---|
| 5-HT1A | 440–1,630 (Ki) >10,000 (Template:Abbrlink) <25% (Template:Abbrlink) | ||
| 5-HT1B | Template:Abbr | ||
| 5-HT1D | Template:Abbr | ||
| 5-HT1E | Template:Abbr | ||
| 5-HT1F | Template:Abbr | ||
| 5-HT2A | 23.9–32.4 (Ki) 43.5–8,130 (Template:Abbr) 6–93% (Template:Abbr) | ||
| 5-HT2B | Template:Abbr (Ki) 230 (Template:Abbr) 77% (Template:Abbr) | ||
| 5-HT2C | 12.7–150 (Ki) 71.1–18,600 (Template:Abbr) 48–100% (Template:Abbr) | ||
| 5-HT3 | Template:Abbr | ||
| 5-HT4 | Template:Abbr | ||
| 5-HT5A | Template:Abbr | ||
| 5-HT6 | Template:Abbr | ||
| 5-HT7 | Template:Abbr | ||
| α1A | 12,000 | ||
| α1B, α1D | Template:Abbr | ||
| α2A | 290 | ||
| α2B, α2C | Template:Abbr | ||
| β1–β3 | Template:Abbr | ||
| D1 | 24,000 | ||
| D2 | 7,100 | ||
| D3 | >17,000 | ||
| D4 | Template:Abbr | ||
| D5 | Template:Abbr | ||
| H1 | >25,000 | ||
| H2–H4 | Template:Abbr | ||
| M1–M5 | Template:Abbr | ||
| I1 | Template:Abbr | ||
| σ1, σ2 | Template:Abbr | ||
| Template:Abbrlink | 3,500 (Ki) (mouse) 150 (Ki) (rat) 2,000 (Template:Abbr) (mouse) 490 (Template:Abbr) (rat) >10,000 (Template:Abbr) (human) 61% (Template:Abbr) (mouse) 55% (Template:Abbr) (rat) | ||
| Template:Abbrlink | 31,000 (Ki) 77,000 (Template:Abbrlink) Template:Abbr (Template:Abbr) | ||
| Template:Abbrlink | >30,000 (Ki) 45,000 (Template:Abbr) Template:Abbr (Template:Abbr) | ||
| Template:Abbrlink | >30,000 (Ki) 626,000 (Template:Abbr) Template:Abbr (Template:Abbr) | ||
| Template:Abbrlink | Template:Abbr (Template:Abbr) | ||
| Template:Abbrlink | 24,000 (Template:Abbr) | ||
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: <ref name="PDSPKiDatabase">{{#invoke:citation/CS1|citation | CitationClass=web
}}</ref><ref name="BindingDB">{{#invoke:citation/CS1|citation |
CitationClass=web
}}</ref><ref name="RickliLuethiReinisch2015">Template:Cite journal</ref><ref name="EshlemanForsterWolfrum2014">Template:Cite journal</ref><ref name="PottieCannaertStove2020">Template:Cite journal</ref><ref name="MoyaBergGutiérrez-Hernandez2007" /><ref name="Acuña-CastilloVillalobosMoya2002" /><ref name="SimmlerBuchyChaboz2016">Template:Cite journal</ref> | |
2C-D is a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.<ref name="RickliLuethiReinisch2015" /><ref name="EshlemanForsterWolfrum2014" /><ref name="MoyaBergGutiérrez-Hernandez2007">Template:Cite journal</ref><ref name="Acuña-CastilloVillalobosMoya2002">Template:Cite journal</ref>
Society and cultureEdit
Legal statusEdit
CanadaEdit
As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
ChinaEdit
As of October 2015 2C-D is a controlled substance in China.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
DenmarkEdit
2C-D is added to the list of Schedule B controlled substances.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
FinlandEdit
Listed in the government decree on psychoactive substances banned from the consumer market.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
GermanyEdit
2C-D is an Anlage I controlled drug.
SwedenEdit
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-D as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
United StatesEdit
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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> On a state level, both Oklahoma and Pennsylvania list 2C-D under schedule I.
See alsoEdit
ReferencesEdit
External linksEdit
- 2C-D - Isomer Design
- 2C-D - PsychonautWiki
- 2C-D - Erowid
- 2C-D - PiHKAL - Erowid
- 2C-D - PiHKAL - Isomer Design
- 2C-D: The Intersect Between DOM & 2C-B - Tripsitter
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