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Names | |||
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Preferred IUPAC name
2-(2,5-Dimethoxy-4-methylphenyl)ethan-1-amine | |||
Other names
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Identifiers | |||
3D model (JSmol) |
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ChEMBL | |||
ChemSpider |
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PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C11H17NO2 | |||
Molar mass | 195.262 g·mol−1 | ||
Melting point | 213 to 214 °C (415 to 417 °F; 486 to 487 K) (hydrochloride) | ||
Pharmacology | |||
Legal status |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2C-D (2,5-dimethoxy-4-methylphenethylamineor2C-M) 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,[1] 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.[2] Lower doses of 10 mg or less have been explored for microdosing.[3]
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.[2] 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.[citation needed]
As of October 2015 2C-D is a controlled substance in China.[4]
As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.[5]
2C-D is added to the list of Schedule B controlled substances.[6]
Listed in the government decree on psychoactive substances banned from the consumer market.[7][8]
2C-D is an Anlage I controlled drug.
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.[9]
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.[10] On a state level, both Oklahoma and Pennsylvania list 2C-D under schedule I.
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Phenethylamines |
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Amphetamines |
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Phentermines |
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Cathinones |
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Phenylisobutylamines |
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Phenylalkylpyrrolidines |
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Catecholamines (and close relatives) |
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Miscellaneous |
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