CYB210010

CYB210010
Clinical data
Other names	CYB-210010; CYB-2108; CYB2108
Identifiers
	IUPAC name 2-[2,5-dimethoxy-4-(trifluoromethylsulfanyl)phenyl]ethanamine;
PubChem CID	168072159;
Chemical and physical data
Formula	C11H14F3NO2S
Molar mass	281.29 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1CCN)OC)SC(F)(F)F;
	InChI InChI=1S/C11H14F3NO2S/c1-16-8-6-10(18-11(12,13)14)9(17-2)5-7(8)3-4-15/h5-6H,3-4,15H2,1-2H3; Key:VOGDBAZLGHXJBS-UHFFFAOYSA-N;

CYB210010, also known as 2C-T-TFM, is a lesser-known psychedelic drug of the phenethylamine family related to compounds such as 2C-T and 2C-T-21.^[2]^[3]

Alexander Shulgin attempted to synthesise this compound in the 1990s, and mentions it in his book PiHKAL under the entry for 2C-T-21, but was unsuccessful in producing a key intermediate and never assigned it a 2C-T number. This compound was ultimately first synthesised by Geoffrey Varty and colleagues at Irish biopharmaceutical company Cybin in 2023.^[3]

It has a K_i of 0.35 nM at the serotonin 5-HT_2A receptor, and an EC₅₀Tooltip half-maximal effective concentration of 4.1 nM at the serotonin 5-HT_2A receptor and 7.3 nM at the serotonin 5-HT_2C receptor, compared to 88 nM at the serotonin 5-HT_2B receptor.^[4] It is a potent, selective, long acting, and orally active agonist for the serotonin 5-HT_2A and 5-HT_2C receptors and produces psychedelic-like responding in several different animal species.^[2]^[3] It has only been studied preclinically as of 2024 and is not known to have been tested in humans.^[2]^[3]

Related drugs include the deuterated phenethylamine CYB005 and the deuterated substituted tryptamines CYB003 and CYB004.^[5]^[6]

References

^ "2-[2,5-Dimethoxy-4-(trifluoromethylsulfanyl)phenyl]ethanamine". PubChem. Retrieved 10 November 2024.
^ ^a ^b ^c Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). "Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist". Journal of Medicinal Chemistry. 67 (8): 6144–6188. doi:10.1021/acs.jmedchem.3c01961. PMID 38593423.
^ ^a ^b ^c ^d Palfreyman M, Varty G, Canal C, Hartsel J, Tyagi R, Avery K, et al. (December 2023). "ACNP 62nd Annual Meeting: Poster Abstracts P251 – P500: P405. Discovery and Preclinical Characterization of the Phenylalkylamine, CYB210010, a Potent and Long-Acting Serotonin 5-HT2A Receptor Agonist". Neuropsychopharmacology. 48 (Suppl 1): 211–354 (299–299. doi:10.1038/s41386-023-01756-4. PMC 10729596. PMID 38040810.
^ WO 2023156450, Nivorozhkin A, JA Hartsel, Canal CE, Salituro FG, Mueller TA, Greene BJ, Belser A, Avery KL, Reichelt AC, Varty GB, Palfreyman M, "Therapeutic phenethylamine compositions and methods of use", published 24 August 2023, assigned to Cybin Irl Limited
^ Cano GH, Dean J, Abreu SP, Rodríguez AH, Abbasi C, Hinson M, et al. (December 2022). "Key Characteristics and Development of Psychoceuticals: A Review". Int J Mol Sci. 23 (24): 15777. doi:10.3390/ijms232415777. PMC 9779201. PMID 36555419.
^ Peplow M (June 2024). "Next-generation psychedelics: should new agents skip the trip?". Nat Biotechnol. 42 (6): 827–830. doi:10.1038/s41587-024-02285-1. PMID 38831049.

[PubChem-1] "2-[2,5-Dimethoxy-4-(trifluoromethylsulfanyl)phenyl]ethanamine". PubChem. Retrieved 10 November 2024.

[VartyCanalMueller2024-2] Varty GB, Canal CE, Mueller TA, Hartsel JA, Tyagi R, Avery K, et al. (April 2024). "Synthesis and Structure-Activity Relationships of 2,5-Dimethoxy-4-Substituted Phenethylamines and the Discovery of CYB210010: A Potent, Orally Bioavailable and Long-Acting Serotonin 5-HT2 Receptor Agonist". Journal of Medicinal Chemistry. 67 (8): 6144–6188. doi:10.1021/acs.jmedchem.3c01961. PMID 38593423.

[PalfreymanVartyCanal2023-3] Palfreyman M, Varty G, Canal C, Hartsel J, Tyagi R, Avery K, et al. (December 2023). "ACNP 62nd Annual Meeting: Poster Abstracts P251 – P500: P405. Discovery and Preclinical Characterization of the Phenylalkylamine, CYB210010, a Potent and Long-Acting Serotonin 5-HT2A Receptor Agonist". Neuropsychopharmacology. 48 (Suppl 1): 211–354 (299–299. doi:10.1038/s41386-023-01756-4. PMC 10729596. PMID 38040810.

[WO2023156450A1-4] WO 2023156450, Nivorozhkin A, JA Hartsel, Canal CE, Salituro FG, Mueller TA, Greene BJ, Belser A, Avery KL, Reichelt AC, Varty GB, Palfreyman M, "Therapeutic phenethylamine compositions and methods of use", published 24 August 2023, assigned to Cybin Irl Limited

[CanoDeanAbreu2022-5] Cano GH, Dean J, Abreu SP, Rodríguez AH, Abbasi C, Hinson M, et al. (December 2022). "Key Characteristics and Development of Psychoceuticals: A Review". Int J Mol Sci. 23 (24): 15777. doi:10.3390/ijms232415777. PMC 9779201. PMID 36555419.

[Peplow2024-6] Peplow M (June 2024). "Next-generation psychedelics: should new agents skip the trip?". Nat Biotechnol. 42 (6): 827–830. doi:10.1038/s41587-024-02285-1. PMID 38831049.

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v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

See also

References