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2C-D

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2C-D
Clinical data
Other names2,5-Dimethoxy-4-methyl-phenethylamine; 4-Methyl-2,5-dimethoxyphenethylamine; 2C-M; LE-25; LE25
Routes of
administration		Oral
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of action4–6 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
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
Melting point213 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 checkY
  • Key:UNQQFDCVEMVQHM-UHFFFAOYSA-N checkY
 ☒NcheckY (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. 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]

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.[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

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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

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2C-D activities
Target Affinity (Ki, nM)
5-HT1A 440–1,630 (Ki)
>10,000 (EC50Tooltip half-maximal effective concentration)
<25% (EmaxTooltip maximal efficacy)
5-HT1B–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-HT3–5-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
TAAR1Tooltip Trace amine-associated receptor 1 3,500 (Ki) (mouse)
150 (Ki) (rat)
2,000 (EC50) (mouse)
490 (EC50) (rat)
>10,000 (EC50) (human)
61% (Emax) (mouse)
55% (Emax) (rat)
SERTTooltip Serotonin transporter 31,000 (Ki)
77,000 (IC50Tooltip half-maximal inhibitory concentration)
IA (EC50)
NETTooltip Norepinephrine transporter >30,000 (Ki)
45,000 (IC50)
IA (EC50)
DATTooltip Dopamine transporter >30,000 (Ki)
626,000 (IC50)
IA (EC50)
MAO-ATooltip Monoamine oxidase A ND (IC50)
MAO-BTooltip Monoamine oxidase B 24,000 (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]

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China

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As of October 2015 2C-D is a controlled substance in China.[15]

Canada

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As of October 31, 2016; 2C-D is a controlled substance (Schedule III) in Canada.[16]

Denmark

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

Finland

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

Germany

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2C-D is an Anlage I controlled drug.

Sweden

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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.[20]

United States

[edit]

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

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  1. ^ a b c 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. ^ a b c 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. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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. ^ a b 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. ^ "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.
  16. ^ "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.
  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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