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The substance is consumed as a [[recreational drug]], and is circulated in the drug market in a powder form. 2C-I is sometimes confused with other related chemical substances such as [[25I-NBOMe|25I-NBOMe (2C-I-NBOMe)]], nicknamed "Smiles" and "N-bomb" in the media.<ref>{{cite web |title=25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths |url=http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}</ref><ref name="weiss">Weiss, Piper (September 20, 2012). [http://shine.yahoo.com/healthy-living/2c-smiles-killer-drug-every-parent-know-234200299.html 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About.] ''[[Yahoo! News]]''</ref><ref name="mackin2012">{{cite web | vauthors = Mackin T | date = October 9, 2012 | url = http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country | title = Dangerous synthetic drug making its way across the country. | archive-url = https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country| archive-date=October 31, 2012}} [[WISH-TV]]</ref>
The substance is consumed as a [[recreational drug]], and is circulated in the drug market in a powder form. 2C-I is sometimes confused with other related chemical substances such as [[25I-NBOMe|25I-NBOMe (2C-I-NBOMe)]], nicknamed "Smiles" and "N-bomb" in the media.<ref>{{cite web |title=25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths |url=http://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}</ref><ref name="weiss">Weiss, Piper (September 20, 2012). [http://shine.yahoo.com/healthy-living/2c-smiles-killer-drug-every-parent-know-234200299.html 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About.] ''[[Yahoo! News]]''</ref><ref name="mackin2012">{{cite web | vauthors = Mackin T | date = October 9, 2012 | url = http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country | title = Dangerous synthetic drug making its way across the country. | archive-url = https://web.archive.org/web/20121031163611/http://www.wishtv.com/dpp/news/indiana/dangerous-synthetic-drug-smiles-making-its-way-across-the-country| archive-date=October 31, 2012}} [[WISH-TV]]</ref>


==Use==
== Patterns of use ==
In the early 2000s, 2C-I was sold in Dutch [[smart shop]]s as a recreational drug after the drug [[2C-B]] was banned.<ref name="Netherlands 2c-b emergence">{{cite journal | vauthors = de Boer D, Gijzels MJ, Bosman IJ, Maes RA | title = More data about the new psychoactive drug 2C-B | journal = Journal of Analytical Toxicology | volume = 23 | issue = 3 | pages = 227–228 | date = May–June 1999 | pmid = 10369336 | doi = 10.1093/jat/23.3.227 | df = dmy-all | doi-access = free }}</ref>
In the early 2000s, 2C-I was sold in Dutch [[smart shop]]s as a recreational drug after the drug [[2C-B]] was banned.<ref name="Netherlands 2c-b emergence">{{cite journal | vauthors = de Boer D, Gijzels MJ, Bosman IJ, Maes RA | title = More data about the new psychoactive drug 2C-B | journal = Journal of Analytical Toxicology | volume = 23 | issue = 3 | pages = 227–228 | date = May–June 1999 | pmid = 10369336 | doi = 10.1093/jat/23.3.227 | df = dmy-all | doi-access = free }}</ref>


According to the US [[Drug Enforcement Administration]], 2C-I is taken orally or [[Insufflation (medicine)|snorted]] in a powder form.<ref name="reuters2011">Reuters (March 20, 2011). [https://web.archive.org/web/20160306161926/http://in.reuters.com/article/us-drugs-overdose-idINTRE72I3QT20110319 Synthetic drug, subject of proposed bans, kill teen.]</ref>
According to the US [[Drug Enforcement Administration]], 2C-I is taken orally or [[Insufflation (medicine)|snorted]] in a powder form.<ref name="reuters2011">Reuters (March 20, 2011). [https://web.archive.org/web/20160306161926/http://in.reuters.com/article/us-drugs-overdose-idINTRE72I3QT20110319 Synthetic drug, subject of proposed bans, kill teen.]</ref>

⚫
==Interactions==
⚫
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

⚫
2C-I is [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}</ref><ref name="TheobaldMaurer2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-I.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />


==Pharmacology==
==Pharmacology==
Line 149: Line 154:


2C-I is a highly potent [[anti-inflammatory drug]] similarly to various other [[serotonergic psychedelic]]s.<ref name="FlanaganBillacLandry2021">{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = https://www.researchgate.net/publication/360537036 }}</ref> However, 2C-I showed the highest anti-inflammatory [[potency (pharmacology)|potency]] of any other assessed drug in a large series in one study.<ref name="FlanaganBillacLandry2021" /> It was more potent than [[(R)-DOI|(''R'')-DOI]] in terms of anti-inflammatory activity.<ref name="FlanaganBillacLandry2021" />
2C-I is a highly potent [[anti-inflammatory drug]] similarly to various other [[serotonergic psychedelic]]s.<ref name="FlanaganBillacLandry2021">{{cite journal | vauthors = Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD | title = Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore | journal = ACS Pharmacol Transl Sci | volume = 4 | issue = 2 | pages = 488–502 | date = April 2021 | pmid = 33860179 | pmc = 8033619 | doi = 10.1021/acsptsci.0c00063 | url = https://www.researchgate.net/publication/360537036 }}</ref> However, 2C-I showed the highest anti-inflammatory [[potency (pharmacology)|potency]] of any other assessed drug in a large series in one study.<ref name="FlanaganBillacLandry2021" /> It was more potent than [[(R)-DOI|(''R'')-DOI]] in terms of anti-inflammatory activity.<ref name="FlanaganBillacLandry2021" />

⚫
==Interactions==
⚫
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

⚫
2C-I is [[drug metabolism|metabolized]] by the [[monoamine oxidase]] (MAO) [[enzyme]]s [[MAO-A]] and [[MAO-B]].<ref name="DeanStellpflugBurnett2013">{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}</ref><ref name="TheobaldMaurer2007">{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }}</ref> [[Monoamine oxidase inhibitor]]s (MAOIs) such as [[phenelzine]], [[tranylcypromine]], [[moclobemide]], and [[selegiline]] may potentiate the effects of 2C-I.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}}</ref> This may result in [[overdose]] and serious [[toxicity]].<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />


==Chemistry==
==Chemistry==
Line 161: Line 161:
{{2C-I analogues and derivatives}}
{{2C-I analogues and derivatives}}


==Legal status==
==Society and culture==
===Legal status===
[[File:2C-I Powder.jpg|thumb|right|200px|2C-I in powder form.]]
[[File:2C-I Powder.jpg|thumb|right|200px|2C-I in powder form.]]


===European Union===
====Australia====
⚫
2C-I is a schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">[https://www.comlaw.gov.au/Details/F2015L01534 Poisons Standard October 2015]</ref> A schedule 9 drug is outlined in the [[Poisons Act 1964]] as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".<ref>{{Cite web |url=http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement |title=Poisons Act 1964 |access-date=2015-12-13 |archive-url=https://web.archive.org/web/20151222191725/http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument%3A26063P/%24FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement |archive-date=2015-12-22 |url-status=dead }}</ref>
⚫
In December 2003, the [[European Council]] issued a binding order compelling all [[European Union]] member states to ban 2C-I within three months.<ref name="erowid-law">{{cite web|url=http://www.erowid.org/chemicals/2ci/2ci_law.shtml|title=Erowid 2C-I Vault : Legal Status}}</ref>


===Canada===
====Canada====
As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.<ref>[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]</ref>
As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.<ref>[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]</ref>


===Australia===
====European Union====
⚫
In December 2003, the [[European Council]] issued a binding order compelling all [[European Union]] member states to ban 2C-I within three months.<ref name="erowid-law">{{cite web|url=http://www.erowid.org/chemicals/2ci/2ci_law.shtml|title=Erowid 2C-I Vault : Legal Status}}</ref>
⚫
2C-I is a schedule 9 prohibited substance in Australia under the [[Standard for the Uniform Scheduling of Medicines and Poisons|Poisons Standard]] (October 2015).<ref name="Poisons Standard">[https://www.comlaw.gov.au/Details/F2015L01534 Poisons Standard October 2015]</ref> A schedule 9 drug is outlined in the [[Poisons Act 1964]] as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".<ref>{{Cite web |url=http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument:26063P/$FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement |title=Poisons Act 1964 |access-date=2015-12-13 |archive-url=https://web.archive.org/web/20151222191725/http://www.slp.wa.gov.au/pco/prod/FileStore.nsf/Documents/MRDocument%3A26063P/%24FILE/Poisons%20Act%201964%20-%20%5B09-f0-04%5D.pdf?OpenElement |archive-date=2015-12-22 |url-status=dead }}</ref>


===Sweden===
====Sweden====
[[Riksdag|''Sveriges riksdag'']] added 2C-I to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as a narcotic on March 16, 2004, published by the [[Medical Products Agency (Sweden)|''Medical Products Agency'']] in their regulation '''LVFS 2004:3'''.<ref>{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling | language = sv}}</ref>
[[Riksdag|''Sveriges riksdag'']] added 2C-I to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as a narcotic on March 16, 2004, published by the [[Medical Products Agency (Sweden)|''Medical Products Agency'']] in their regulation LVFS 2004:3.<ref>{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling | language = sv}}</ref>


===United Kingdom===
====United Kingdom====
In the United Kingdom, 2C-I is controlled as a [[Drugs controlled by the UK Misuse of Drugs Act|Class A]] substance.<ref name="erowid-law" />
In the United Kingdom, 2C-I is controlled as a [[Drugs controlled by the UK Misuse of Drugs Act|Class A]] substance.<ref name="erowid-law" />


===United States===
====United States====
As of July 9, 2012, in the [[United States]] 2C-I is a [[Schedule I controlled substance|Schedule I]] substance under the [[Synthetic Drug Abuse Prevention Act of 2012]], making possession, distribution and manufacture illegal.<ref name="erowid-law" /> A previous bill, introduced in March 2011, that would have done the same passed the House of Representatives, but was not passed by the Senate.<ref>{{cite web|title=H.R. 1254 (112th): Synthetic Drug Control Act of 2011|url=https://www.govtrack.us/congress/bills/112/hr1254|website=GovTrack|access-date=30 September 2015}}</ref>
As of July 9, 2012, in the [[United States]] 2C-I is a [[Schedule I controlled substance|Schedule I]] substance under the [[Synthetic Drug Abuse Prevention Act of 2012]], making possession, distribution and manufacture illegal.<ref name="erowid-law" /> A previous bill, introduced in March 2011, that would have done the same passed the House of Representatives, but was not passed by the Senate.<ref>{{cite web|title=H.R. 1254 (112th): Synthetic Drug Control Act of 2011|url=https://www.govtrack.us/congress/bills/112/hr1254|website=GovTrack|access-date=30 September 2015}}</ref>


Revision as of 15:37, 1 April 2025

2C-I
Legal status
Legal status
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.217.507 Edit this at Wikidata
Chemical and physical data
FormulaC10H14INO2
Molar mass307.131 g·mol−1
3D model (JSmol)
Melting point246 °C (475 °F)
  • Ic1cc(OC)c(cc1OC)CCN
  • InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 checkY
  • Key:PQHQBRJAAZQXHL-UHFFFAOYSA-N checkY
  (verify)

2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects.[1] It was first synthesized by Alexander Shulgin, and is described in Shulgin's book PiHKAL (1991).

The substance is consumed as a recreational drug, and is circulated in the drug market in a powder form. 2C-I is sometimes confused with other related chemical substances such as 25I-NBOMe (2C-I-NBOMe), nicknamed "Smiles" and "N-bomb" in the media.[2][3][4]

Use

In the early 2000s, 2C-I was sold in Dutch smart shops as a recreational drug after the drug 2C-B was banned.[5]

According to the US Drug Enforcement Administration, 2C-I is taken orally or snorted in a powder form.[6]

Interactions

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

2C-I is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.[7][8] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-I.[7][8][9] This may result in overdose and serious toxicity.[9][7]

Pharmacology

Pharmacodynamics

2C-I activities
Target Affinity (Ki, nM)
5-HT1A 180–970 (Ki)
4,900 (EC50Tooltip half-maximal effective concentration)
102% (EmaxTooltip maximal efficacy)
5-HT1B–5-HT1F ND
5-HT2A 3.5–9.3 (Ki)
1.48–513 (EC50)
17–93% (Emax)
5-HT2B 19.1–150 (EC50)
70–101% (Emax)
5-HT2C 10–40 (Ki)
0.46–537 (EC50)
44–107% (Emax)
5-HT3–5-HT7 ND
α1A 5,100
α1B, α1D ND
α2A 70
α2B, α2C ND
β1–β3 ND
D1 13,000
D2 2,700
D3 5,000
D4, D5 ND
H1 6,100
TAAR1Tooltip Trace amine-associated receptor 1 3,300 (Ki) (mouse)
120 (Ki) (rat)
2,400 (EC50) (mouse)
190 (EC50) (rat)
>10,000 (EC50) (human)
51% (Emax) (mouse)
50% (Emax) (rat)
SERTTooltip Serotonin transporter 950–4,900 (Ki)
5,600–13,000 (IC50Tooltip half-maximal inhibitory concentration)
IA (EC50)
NETTooltip Norepinephrine transporter 15,000 (Ki)
22,000 (IC50)
IA (EC50)
DATTooltip Dopamine transporter >30,000 (Ki)
126,000 (IC50)
IA (EC50)
MAO-ATooltip Monoamine oxidase A 125,000 (IC50)
MAO-BTooltip Monoamine oxidase B 55,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [10][11][12][13]
[14][15][16][17][18][19]

2C-I acts as a serotonin receptor agonist. It produces psychedelic effects via serotonin 5-HT2A receptor activation.

It is inactive as a monoamine releasing agent and shows negligible activity as a monoamine reuptake inhibitor.[12][11]

2C-I is a highly potent anti-inflammatory drug similarly to various other serotonergic psychedelics.[17] However, 2C-I showed the highest anti-inflammatory potency of any other assessed drug in a large series in one study.[17] It was more potent than (R)-DOI in terms of anti-inflammatory activity.[17]

Chemistry

Analogues and derivatives

DOI

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

Society and culture

2C-I in powder form.

Australia

2C-I is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[21] A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO".[22]

Canada

As of October 31, 2016, 2C-I is a controlled substance (Schedule III) in Canada.[23]

European Union

In December 2003, the European Council issued a binding order compelling all European Union member states to ban 2C-I within three months.[24]

Sweden

Sveriges riksdag added 2C-I to schedule I ("substances, plant materials and fungi which normally do not have medical use") as a narcotic on March 16, 2004, published by the Medical Products Agency in their regulation LVFS 2004:3.[25]

United Kingdom

In the United Kingdom, 2C-I is controlled as a Class A substance.[24]

United States

As of July 9, 2012, in the United States 2C-I is a Schedule I substance under the Synthetic Drug Abuse Prevention Act of 2012, making possession, distribution and manufacture illegal.[24] A previous bill, introduced in March 2011, that would have done the same passed the House of Representatives, but was not passed by the Senate.[26]

See also

References

  1. ^ Bosak A, LoVecchio F, Levine M (June 2013). "Recurrent seizures and serotonin syndrome following "2C-I" ingestion". Journal of Medical Toxicology. 9 (2): 196–198. doi:10.1007/s13181-013-0287-x. PMC 3657032. PMID 23378129.
  2. ^ "25I-NBOMe (2C-I-NBOMe): Fatalities / Deaths".
  3. ^ Weiss, Piper (September 20, 2012). 2C-I or 'Smiles': The New Killer Drug Every Parent Should Know About. Yahoo! News
  4. ^ Mackin T (October 9, 2012). "Dangerous synthetic drug making its way across the country". Archived from the original on October 31, 2012. WISH-TV
  5. ^ de Boer D, Gijzels MJ, Bosman IJ, Maes RA (May–June 1999). "More data about the new psychoactive drug 2C-B". Journal of Analytical Toxicology. 23 (3): 227–228. doi:10.1093/jat/23.3.227. PMID 10369336.
  6. ^ Reuters (March 20, 2011). Synthetic drug, subject of proposed bans, kill teen.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ "Kᵢ Database". PDSP. 16 March 2025. Retrieved 16 March 2025.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1): 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
  15. ^ 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.
  16. ^ Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, et al. (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.
  17. ^ a b c d Flanagan TW, Billac GB, Landry AN, Sebastian MN, Cormier SA, Nichols CD (April 2021). "Structure-Activity Relationship Analysis of Psychedelics in a Rat Model of Asthma Reveals the Anti-Inflammatory Pharmacophore". ACS Pharmacol Transl Sci. 4 (2): 488–502. doi:10.1021/acsptsci.0c00063. PMC 8033619. PMID 33860179.
  18. ^ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Test Anal. 11 (2): 318–324. doi:10.1002/dta.2494. PMID 30188017.
  19. ^ 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.
  20. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
  21. ^ Poisons Standard October 2015
  22. ^ "Poisons Act 1964" (PDF). Archived from the original (PDF) on 2015-12-22. Retrieved 2015-12-13.
  23. ^ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
  24. ^ a b c "Erowid 2C-I Vault : Legal Status".
  25. ^ "Läkemedelsverkets författningssamling" (PDF) (in Swedish).
  26. ^ "H.R. 1254 (112th): Synthetic Drug Control Act of 2011". GovTrack. Retrieved 30 September 2015.
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