2C-D

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2C-D's dose range as 20 to 60mg orally and its duration as 4 to 6hours. He describes threshold effects as occurring at a dose of 6mg orally and full intoxication occurring at doses of 10 to 15mg orally. Higher doses of 75 to 200mg orally have also been described and were well-tolerated. In addition, a wider recreational dose range of 3 to 100mg or more has been described. The onset is said to be 20 to 30minutes and peak effects occur after 1.5 to 2hours. Casey Hardison has described 2C-D as having a very gentle dose–response curve with an unusually wide dose range.

The effects of 2C-D have been described. At low doses, it produces perceived cognitive enhancement, mild stimulant-like effects, emotional integration, euphoria, and mild psychedelic effects such as perceptual enhancement that are much lighter than those of conventional psychedelics. At high doses, it produces robust psychedelic effects. Shulgin referred to 2C-D as a "pharmacological tofu" because it didn't have especially pronounced effects on its own until very high doses were reached but could be combined with and extend or potentiate the effects of other psychedelics without coloring their experiences.

Hanscarl Leuner, working in Germany, explored the use of 2C-D under the code name LE-25 in psychedelic-assisted psychotherapy at doses of up to 150 to 200mg orally. Low doses of 2C-D in the range of 5 to 10mg orally have been explored as a "smart drug" by Darrell Lemaire.

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

Pharmacodynamics

2C-D acts as a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.

Chemistry

Synthesis

The chemical synthesis of 2C-D has been described.

Analogues

Analogues of 2C-D include 2C-B, 2C-E, 2C-P, other 2Cs, DOM (α-methyl-2C-D), Ariadne (4C-D; α-ethyl-2C-D), 5C-D (α-propyl-2C-D), and TWEETIOs like 2CD-5-ETO, among others. Other notable derivatives of 2C-D include 2C-G (3-methyl-2C-D) and other compounds of the 2C-G series like 2C-G-3 and 2C-G-5.

History

2C-D was first described in the scientific literature by Beng T. Ho and colleagues at the Texas Research Institute of Mental Sciences in 1970. They described its synthesis and pharmacological effects in animals. The properties and effects of 2C-D in humans, along with those of 2C-B, were described by Alexander Shulgin and Michael Carter in 1975. Shulgin had first tested 2C-D at sub-threshold doses in 1964 and 1965. Subsequently, he tested it at higher doses in 1974 and 1975 and discovered its psychoactive effects.

Hanscarl Leuner and his student Michael Schlichting extensively studied 2C-D at high doses in psychedelic-assisted psychotherapy in Germany in the 1970s and 1980s. Darrell Lemaire, under the pseudonyms Hosteen Nez and/or Lazar, studied 2C-D at low doses as a potential "smart drug" in the 1970s and 1980s.

2C-D was encountered as a novel recreational designer drug in the United States by 2005. It was not a controlled substance in the United States or most other countries at this time, in contrast to more popular 2Cs like 2C-B and 2C-T-7. The drug became a Schedule I controlled substance in the United States in 2012.

Society and culture

Legal status

Canada

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

China

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

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 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.

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.

References

References

1. "2C-D".
2. (November 2006). "Studies on the metabolism and toxicological detection of the designer drug 2,5-dimethoxy-4-methyl-beta- phenethylamine (2C-D) in rat urine using gas chromatographic/mass spectrometric techniques". Journal of Mass Spectrometry.
3. (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". The International Journal of Neuropsychopharmacology.
4. (1 July 2007). "A brief history and motivation of an entheogenic chemist". Drugs and Alcohol Today.
5. {{CiteTiHKAL "At a banquet associated with an international conference on the study of consciousness, held in Göttingen a few years ago, Alice and I had the pleasure of sitting at the table with Hanscarl Leuner and his wife. He thanked me for inventing 2C-D which he and his students had been exploring as an adjunct to psychotherapy. They had renamed it, initially DMM-PEA and then LE-25, and had apparently explored it at dosages that reached into the hundreds of milligrams. In PIHKAL, I had offered an effective range for this drug of from 20 to 60 milligrams. It would seem that in his later years, Dr. Leuner chose to move from the psycholytic camp over to the psychedelic camp."
6. (1990). "Certain Exotic Transmitters as Smart Pills or Compounds that Increase the Capacity for Mental Work in Humans: A Story About LAZAR as Told by Hosteen Nez".
7. (7 December 2016). "The Lazy Lizard School of Hedonism". [[Vice Media]].
8. (June 2013). "2C or not 2C: phenethylamine designer drug review". Journal of Medical Toxicology.
9. (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochemical Pharmacology.
10. (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology.
11. (16 March 2025). "Kᵢ Database".
12. "BindingDB BDBM50240787 2-(4-Methyl-2,5-dimethoxy-phenyl)-ethylamine::2-(4-methyl-2,5-dimethoxyphenyl)ethylamine::CHEMBL124049".
13. (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)". Neuropharmacology.
14. (March 2014). "Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function". Psychopharmacology.
15. (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Archives of Toxicology.
16. (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". The Journal of Pharmacology and Experimental Therapeutics.
17. (June 2007). "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors". The Journal of Pharmacology and Experimental Therapeutics.
18. (June 2002). "Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors". British Journal of Pharmacology.
19. (August 2023). "Structure-Activity Assessment and In-Depth Analysis of Biased Agonism in a Set of Phenylalkylamine 5-HT2A Receptor Agonists". ACS Chem Neurosci.
20. (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". [[Transform Press]].
21. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
22. (1975). "Hallucinogenic Agents". Wright-Scientechnica.
23. (January 1970). "Amphetamine analogs. II. Methylated phenethylamines". Journal of Medicinal Chemistry.
24. (1975). "Centrally active phenethylamines". Psychopharmacology Communications.
25. "Subacute evaluation, 2-C-DOM!". PiHKAL.
26. "Acute Trials, 2-C-DOM!". PiHKAL.
27. (December 2020). "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience.
28. (2024). "A history of the European Medical Society for Psycholytic Therapy (EPT) 1964–1974". Drug Science, Policy and Law.
29. (7 November 2022). "Handbook of Medical Hallucinogens". Guilford Publications.
30. (1981). "Halluzinogene: psychische Grenzzustände in Forschung und Psychotherapie". Huber.
31. "Psychotrope Eigenschaften des Phenäthylamins DMM-PEA (2,5-dimethoxy-4-methyl-phenathylamin)". Göttingen University.
32. "Erowid Darrell Lemaire Vault".
33. Hosteen Nez ([[Darrell Lemaire]]). (2010). "Radiant Minds: Scientists Explore the Dimensions of Consciousness". Millay.
34. (4 May 2016). "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)".
35. (27 September 2015). "关于印发《非药用类麻醉药品和精神药品列管办法》的通知". China Food and Drug Administration.
36. "Retsinformation".
37. "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".
38. "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021".
39. "Svensk författningssamling".
40. "S. 3187".