2C-CN

2C-CN
Clinical data
Other names	25CN; 2,5-Dimethoxy-4-cyanophenethylamine; 4-Cyano-2,5-dimethoxyphenethylamine
Identifiers
	IUPAC name 4-(2-aminoethyl)-2,5-dimethoxybenzonitrile;
CAS Number	88441-07-0;
PubChem CID	57474247;
ChemSpider	28690053;
UNII	68O9X0114E;
CompTox Dashboard (EPA)	DTXSID00726819 ;
Chemical and physical data
Formula	C11H14N2O2
Molar mass	206.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1CCN)OC)C#N;
	InChI InChI=1S/C11H14N2O2/c1-14-10-6-9(7-13)11(15-2)5-8(10)3-4-12/h5-6H,3-4,12H2,1-2H3; Key:OGWCKYKYGQORLF-UHFFFAOYSA-N;

2C-CN, also known as 4-cyano-2,5-dimethoxyphenethylamine, is a chemical compound of the phenethylamine and 2C families.^[1]^[2]^[3]^[4]^[5]^[6] It was not known to have been tested in humans and it is unknown whether it produces psychedelic effects.^[1]^[2] According to Daniel Trachsel however, 2C-CN was inactive at an oral dose of 10 mg, whereas an oral dose of 22 mg possibly produced threshold effects.^[7]

The drug is the 2C parent compound of potent serotonin 5-HT_2A receptor agonists of the 25-NB family including 25CN-NBOH, 25CN-NBOMe, 25CN-NBF, and 25CN-NBMD, among others.^[8]^[9]^[10]^[6]^[11]^[12] 25CN-NBOH is notable in being one of the most selective serotonin 5-HT_2A receptor agonists known.^[8]^[11] In addition, 25-NB derivatives of 2C-CN are known that act as β-arrestin-biased serotonin 5-HT_2A receptor agonists.^[6]

2C-CN was first described in the scientific literature by 1984.^[3] It was briefly mentioned by Alexander Shulgin in his books PiHKAL (Phenethylamines I Have Known and Loved) (1991) and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011).^[1]^[2]

References

^ ^a ^b ^c Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The treatment of the 2C-B phthalimide described above, with cuprous cyanide rather than cuprous chloride, gave rise to the cyano analog which, on hydrolysis with hydrazine, yielded 2,5-dimethoxy-4-cyanophenethylamine (2C-CN). Hydrolysis of this with hot, strong base gave the corresponding acid, 2,5-dimethoxy-4-carboxyphenethylamine, 2C-COOH. No evaluation of either of these compounds has been made in the human animal, as far as I know."
^ ^a ^b ^c Shulgin A, Manning T, Daley PF (2011). "#55. DOCN". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 105–106. ISBN 978-0-9630096-3-0. OCLC 709667010.
^ ^a ^b Cheng AC, Castagnoli N (April 1984). "Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogues of 6-hydroxydopamine". Journal of Medicinal Chemistry. 27 (4): 513–520. doi:10.1021/jm00370a014. PMID 6423824.
^ Leth-Petersen S, Bundgaard C, Hansen M, Carnerup MA, Kehler J, Kristensen JL (October 2014). "Correlating the metabolic stability of psychedelic 5-HT₂A agonists with anecdotal reports of human oral bioavailability". Neurochemical Research. 39 (10): 2018–2023. doi:10.1007/s11064-014-1253-y. PMID 24519542.
^ Märcher-Rørsted E, Nykodemová J, Kristensen JL (April 2021). "An improved, scalable synthesis of the selective serotonin 2A receptor agonist 25CN-NBOH". Synopen. 5 (2): 158–160. doi:10.1055/a-1524-4439.
^ ^a ^b ^c Poulie CB, Pottie E, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, et al. (September 2022). "Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists". Journal of Medicinal Chemistry. 65 (18): 12031–12043. doi:10.1021/acs.jmedchem.2c00702. PMC 9511481. PMID 36099411.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025. Die Substanz 2C-CN (186) [87] trägt eine Nitrilgruppe in der 4-Position. Aufgrund der polaren Nitrilgruppe und den tieferen Affinitäten des 3C-Analogons DOCN (187) zum 5-HT2A-Rezeptor (siehe Tabelle 10) kann eine schwache Aktivität im Menschen vermutet werden. Das deckt sich mit ersten Versuchen am Menschen, wonach 10mg 2C-CN (186) oral keinerlei Effekte zeigten und 22mg lediglich als mögliche Schwellendosis bezeichnet wurden.
^ ^a ^b Märcher Rørsted E, Jensen AA, Kristensen JL (November 2021). "25CN-NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor". ChemMedChem. 16 (21): 3263–3270. doi:10.1002/cmdc.202100395. PMID 34288515.
^ Jensen AA, McCorvy JD, Leth-Petersen S, Bundgaard C, Liebscher G, Kenakin TP, et al. (June 2017). "Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2,5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist". The Journal of Pharmacology and Experimental Therapeutics. 361 (3): 441–453. doi:10.1124/jpet.117.239905. PMID 28360333.
^ Jensen AA, Halberstadt AL, Märcher-Rørsted E, Odland AU, Chatha M, Speth N, et al. (July 2020). "The selective 5-HT_2A receptor agonist 25CN-NBOH: Structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [³H]25CN-NBOH". Biochemical Pharmacology. 177: 113979. doi:10.1016/j.bcp.2020.113979. PMID 32298690.{{cite journal}}: CS1 maint: article number as page number (link)
^ ^a ^b Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020). "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience. 11 (23): 3860–3869. doi:10.1021/acschemneuro.9b00528. PMC 9191638. PMID 31657895.
^ Slocum ST, DiBerto JF, Roth BL (July 2022). "Molecular insights into psychedelic drug action". Journal of Neurochemistry. 162 (1): 24–38. doi:10.1111/jnc.15540. PMID 34797943.

External links

2C-CN - Isomer Design

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[PiHKAL-1] Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The treatment of the 2C-B phthalimide described above, with cuprous cyanide rather than cuprous chloride, gave rise to the cyano analog which, on hydrolysis with hydrazine, yielded 2,5-dimethoxy-4-cyanophenethylamine (2C-CN). Hydrolysis of this with hot, strong base gave the corresponding acid, 2,5-dimethoxy-4-carboxyphenethylamine, 2C-COOH. No evaluation of either of these compounds has been made in the human animal, as far as I know."

[Shulgin_2011-2] Shulgin A, Manning T, Daley PF (2011). "#55. DOCN". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 105–106. ISBN 978-0-9630096-3-0. OCLC 709667010.

[Cheng_1984-3] Cheng AC, Castagnoli N (April 1984). "Synthesis and physicochemical and neurotoxicity studies of 1-(4-substituted-2,5-dihydroxyphenyl)-2-aminoethane analogues of 6-hydroxydopamine". Journal of Medicinal Chemistry. 27 (4): 513–520. doi:10.1021/jm00370a014. PMID 6423824.

[LethPetersen_2014-4] Leth-Petersen S, Bundgaard C, Hansen M, Carnerup MA, Kehler J, Kristensen JL (October 2014). "Correlating the metabolic stability of psychedelic 5-HT₂A agonists with anecdotal reports of human oral bioavailability". Neurochemical Research. 39 (10): 2018–2023. doi:10.1007/s11064-014-1253-y. PMID 24519542.

[Märcher-RørstedNykodemováKristensen2021-5] Märcher-Rørsted E, Nykodemová J, Kristensen JL (April 2021). "An improved, scalable synthesis of the selective serotonin 2A receptor agonist 25CN-NBOH". Synopen. 5 (2): 158–160. doi:10.1055/a-1524-4439.

[Poulie_2022-6] Poulie CB, Pottie E, Simon IA, Harpsøe K, D'Andrea L, Komarov IV, et al. (September 2022). "Discovery of β-Arrestin-Biased 25CN-NBOH-Derived 5-HT2A Receptor Agonists". Journal of Medicinal Chemistry. 65 (18): 12031–12043. doi:10.1021/acs.jmedchem.2c00702. PMC 9511481. PMID 36099411.

[Trachsel_2013-7] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025. Die Substanz 2C-CN (186) [87] trägt eine Nitrilgruppe in der 4-Position. Aufgrund der polaren Nitrilgruppe und den tieferen Affinitäten des 3C-Analogons DOCN (187) zum 5-HT2A-Rezeptor (siehe Tabelle 10) kann eine schwache Aktivität im Menschen vermutet werden. Das deckt sich mit ersten Versuchen am Menschen, wonach 10mg 2C-CN (186) oral keinerlei Effekte zeigten und 22mg lediglich als mögliche Schwellendosis bezeichnet wurden.

[Marcher_Rrsted_2021-8] Märcher Rørsted E, Jensen AA, Kristensen JL (November 2021). "25CN-NBOH: A Selective Agonist for in vitro and in vivo Investigations of the Serotonin 2A Receptor". ChemMedChem. 16 (21): 3263–3270. doi:10.1002/cmdc.202100395. PMID 34288515.

[Jensen_2017-9] Jensen AA, McCorvy JD, Leth-Petersen S, Bundgaard C, Liebscher G, Kenakin TP, et al. (June 2017). "Detailed Characterization of the In Vitro Pharmacological and Pharmacokinetic Properties of N-(2-Hydroxybenzyl)-2,5-Dimethoxy-4-Cyanophenylethylamine (25CN-NBOH), a Highly Selective and Brain-Penetrant 5-HT2A Receptor Agonist". The Journal of Pharmacology and Experimental Therapeutics. 361 (3): 441–453. doi:10.1124/jpet.117.239905. PMID 28360333.

[Jensen_2020-10] Jensen AA, Halberstadt AL, Märcher-Rørsted E, Odland AU, Chatha M, Speth N, et al. (July 2020). "The selective 5-HT_2A receptor agonist 25CN-NBOH: Structure-activity relationship, in vivo pharmacology, and in vitro and ex vivo binding characteristics of [³H]25CN-NBOH". Biochemical Pharmacology. 177: 113979. doi:10.1016/j.bcp.2020.113979. PMID 32298690.{{cite journal}}: CS1 maint: article number as page number (link)

[Poulie_2020-11] Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020). "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience. 11 (23): 3860–3869. doi:10.1021/acschemneuro.9b00528. PMC 9191638. PMID 31657895.

[Slocum_2022-12] Slocum ST, DiBerto JF, Roth BL (July 2022). "Molecular insights into psychedelic drug action". Journal of Neurochemistry. 162 (1): 24–38. doi:10.1111/jnc.15540. PMID 34797943.

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2C-CN

See also

References

External links

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