2C-D

Last updated
2C-D
2C-D 2DACS.svg
2C-D-3d-sticks.png
Clinical data
Other names2,5-Dimethoxy-4-methyl-phenethylamine; 4-Methyl-2,5-dimethoxyphenethylamine; 2C-M; LE-25; LE25
Routes of
administration 		Oral
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of action 4–6 hours [1]
Identifiers
  • 2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H17NO2
Molar mass 195.262 g·mol−1
3D model (JSmol)
Melting point 213 to 214 °C (415 to 417 °F) (hydrochloride)
  • O(c1cc(c(OC)cc1CCN)C)C
  • InChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3 Yes check.svgY
  • Key:UNQQFDCVEMVQHM-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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, [2] and its activity was subsequently investigated in humans by Alexander Shulgin.

Contents

Use and effects

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. [1] Lower doses of 10 mg or less have been explored for microdosing. [3] According to Shulgin, the effects of 2C-D typically last for 4–6 hours. [1] 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 ]

Interactions

2C-D is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. [4] [5] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-D. [4] [5] [6] This may result in overdose and serious toxicity. [6] [4]

Pharmacology

2C-D activities
Target Affinity (Ki, nM)
5-HT1A 440–1,630 (Ki)
>10,000 (EC50 Tooltip half-maximal effective concentration)
<25% (Emax Tooltip maximal efficacy)
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 23.9–32.4 (Ki)
43.5–8,130 (EC50)
6–93% (Emax)
5-HT2B ND (Ki)
230 (EC50)
77% (Emax)
5-HT2C 12.7–150 (Ki)
71.1–18,600 (EC50)
48–100% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 12,000
α1B, α1D ND
α2A 290
α2B, α2C ND
β1–β3 ND
D1 24,000
D2 7,100
D3 >17,000
D4 ND
D5 ND
H1 >25,000
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1 Tooltip Trace amine-associated receptor 13,500 (Ki) (mouse)
150 (Ki) (rat)
2,000 (EC50) (mouse)
490 (EC50) (rat)
>10,000 (EC50) (human)
61% (Emax) (mouse)
55% (Emax) (rat)
SERT Tooltip Serotonin transporter31,000 (Ki)
77,000 (IC50 Tooltip half-maximal inhibitory concentration)
IA (EC50)
NET Tooltip Norepinephrine transporter>30,000 (Ki)
45,000 (IC50)
IA (EC50)
DAT Tooltip Dopamine transporter>30,000 (Ki)
626,000 (IC50)
IA (EC50)
MAO-A Tooltip Monoamine oxidase AND (IC50)
MAO-B Tooltip Monoamine oxidase B24,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [7] [8] [9] [10] [11] [12] [13] [14]

2C-D is a partial agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [9] [10] [12] [13]

Society and culture

Canada

As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada. [15]

China

As of October 2015 2C-D is a controlled substance in China. [16]

Denmark

2C-D is added to the list of Schedule B controlled substances. [17]

Finland

Listed in the government decree on psychoactive substances banned from the consumer market. [18] [19]

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. [20]

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. [21] On a state level, both Oklahoma and Pennsylvania list 2C-D under schedule I.

References

  1. 1 2 3 2C-D Entry in PiHKAL
  2. ↑ Ho BT, Tansey LW, Balster RL, An R, McIsaac WM, Harris RT (January 1970). "Amphetamine analogs. II. Methylated phenethylamines". Journal of Medicinal Chemistry. 13 (1): 134–5. doi:10.1021/jm00295a034. PMID   5412084.
  3. ↑ Nez, Hosteen (2015). "Erowid 2C-D Vault : Smart Pills". www.erowid.org. Archived from the original on 2001-07-09. Retrieved 2022-01-09.
  4. 1 2 3 Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol. 9 (2): 172–178. doi:10.1007/s13181-013-0295-x. PMC   3657019 . PMID   23494844.
  5. 1 2 Theobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)". Biochem Pharmacol. 73 (2): 287–297. doi:10.1016/j.bcp.2006.09.022. PMID   17067556.
  6. 1 2 Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". J Psychopharmacol. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC   10851641 . PMID   37982394.
  7. ↑ "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025.
  8. ↑ Liu, Tiqing. "BindingDB BDBM50240787 2-(4-Methyl-2,5-dimethoxy-phenyl)-ethylamine::2-(4-methyl-2,5-dimethoxyphenyl)ethylamine::CHEMBL124049". BindingDB. Retrieved 16 March 2025.
  9. 1 2 Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–553. doi:10.1016/j.neuropharm.2015.08.034. PMID   26318099.
  10. 1 2 Eshleman AJ, Forster MJ, Wolfrum KM, Johnson RA, Janowsky A, Gatch MB (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" (PDF). Psychopharmacology (Berl). 231 (5): 875–888. doi:10.1007/s00213-013-3303-6. PMC   3945162 . PMID   24142203.
  11. ↑ Pottie E, Cannaert A, Stove CP (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". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl: 1854/LU-8687071 . PMID   32627074.
  12. 1 2 Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP (June 2007). "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors" (PDF). J Pharmacol Exp Ther. 321 (3): 1054–1061. doi:10.1124/jpet.106.117507. PMID   17337633.
  13. 1 2 Acuña-Castillo C, Villalobos C, Moya PR, Sáez P, Cassels BK, Huidobro-Toro JP (June 2002). "Differences in potency and efficacy of a series of phenylisopropylamine/phenylethylamine pairs at 5-HT(2A) and 5-HT(2C) receptors". Br J Pharmacol. 136 (4): 510–519. doi:10.1038/sj.bjp.0704747. PMC   1573376 . PMID   12055129.
  14. ↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID   26791601.
  15. ↑ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  16. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  17. ↑ "Retsinformation".
  18. ↑ "FINLEX ® - Ajantasainen lainsäädäntö: Valtioneuvoston asetus kuluttajamarkkinoilta… 1130/2014".
  19. ↑ "FINLEX ® - Säädökset alkuperäisinä: Valtioneuvoston asetus kuluttajamarkkinoilta… 733/2021".
  20. ↑ Johansson, Morgan. "Svensk författningssamling" (PDF). Archived from the original (PDF) on September 29, 2013. Retrieved January 24, 2022.
  21. ↑ "S. 3187". Archived from the original on 2012-12-14. Retrieved 2012-07-11.
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