2C-T-21.5

2C-T-21.5
Identifiers
	IUPAC name 2-[4-(3,3-difluoropropylsulfanyl)-2,5-dimethoxyphenyl]ethanamine;
CAS Number	648957-46-4;
PubChem CID	168072172;
Chemical and physical data
Formula	C13H19F2NO2S
Molar mass	291.36 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=C(C=C1CCN)OC)SCCC(F)F;
	InChI InChI=InChI=1S/C13H19F2NO2S/c1-17-10-8-12(19-6-4-13(14)15)11(18-2)7-9(10)3-5-16/h7-8,13H,3-6,16H2,1-2H3; Key:ZVGABSRADMNWQL-UHFFFAOYSA-N;

2C-T-21.5 is a lesser-known psychedelic drug related to compounds such as 2C-T-21 and 2C-T-28. It was originally named by Alexander Shulgin and discussed in his book PiHKAL,^[1] but was not synthesised at that time. 2C-T-21.5 was ultimately synthesised and tested by Daniel Trachsel some years later. It has a binding affinity of 146 nM at 5-HT_2A and 55 nM at 5-HT_2C. It produces typical psychedelic effects, being slightly less potent but somewhat longer acting than 2C-T-2 or 2C-T-21,^[2]^[3]^[4] with an active dose of 12–30 mg, and a duration of action of 8–14 hours. Unlike 2C-T-21 it will not form the highly toxic fluoroacetate as a metabolite, instead producing the less toxic difluoroacetic acid.^[5]^[6]

References

^ Alexander Shulgin. "2C-T-21". PiHKAL.
^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
^ Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)" (PDF). Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478.
^ Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology. 240 (1): 115–126. doi:10.1007/s00213-022-06279-2. PMC 9816194. PMID 36477925.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 789–791. ISBN 978-3-03788-700-4.
^ WO 2023/156450, Nivorozhkin A, Hartsel JA, 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 Ltd.

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[pihkal-1] Alexander Shulgin. "2C-T-21". PiHKAL.

[2] Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.

[3] Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)" (PDF). Neuropharmacology. 134 (Pt A): 141–148. doi:10.1016/j.neuropharm.2017.07.012. PMID 28720478.

[4] Halberstadt AL, Luethi D, Hoener MC, Trachsel D, Brandt SD, Liechti ME (January 2023). "Use of the head-twitch response to investigate the structure-activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines". Psychopharmacology. 240 (1): 115–126. doi:10.1007/s00213-022-06279-2. PMC 9816194. PMID 36477925.

[5] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 789–791. ISBN 978-3-03788-700-4.

[6] WO 2023/156450, Nivorozhkin A, Hartsel JA, 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 Ltd.

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See also

References