2C-T-21.5 - Wikipedia

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, also known as 4-(2,2-difluoroethylthio)-2,5-dimethoxyphenethylamine, 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

[edit]

^ 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.

No ring subs.	CYB004 (deuDMT) DALT DBT DCPT DET DiPT DMT DPT EiPT EPT MALT MET MiPT MPT NBoc-DMT NMT PiPT Tryptamine (T)
4-Hydroxytryptamines	4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT 4-HO-MALT 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-T 4-HO-TMT 4-HO-5-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT) 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT) 4-Acetoxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-MET (metocetin) 4-AcO-MiPT (mipracetin) 4-GO-DiPT (RE-104, FT-104) 4-GO-DMT (RE-109) 4-PrO-DMT
5-Hydroxytryptamines	Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acetoxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-(t-BuCO)-DMT)
5-Methoxytryptamines	4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NiPT 5-MeO-NMT
Other ring subs.	2,N,N-TMT 4,N,N-TMT 5-Bromo-DMT 5-N,N-TMT 7,N,N-TMT 5-Fluoro-DMT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 6-Fluoro-DMT Bretisilocin (GM-2505; 5-fluoro-MET)
α-Alkyltryptamines	4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) 5-Methoxy-α-alkyltryptamines: 5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT)
Others	N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: ASR-3001 CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004
Cyclized	Ergolines/lysergamides (e.g., LSD) Harmala alkaloids and β-carbolines (e.g., harmine, harmaline) Iboga alkaloids (e.g., 18-MAC, 18-MC, coronaridine, ibogaine, ibogamine, ME-18-MC, noribogaine, tabernanthine, voacangine) Ibogalogs (e.g., ibogainalog) Partial ergolines (e.g., NDTDI, RU-28306, DEIMDHPCA, CT-5252) Piperidinylethylindoles (e.g., Pip-T) Pyrrolidinylethylindoles (e.g., Pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI)
Bioisosteres	Benzofurans (e.g., 5-MeO-DiBF, dimemebfe (5-MeO-BFE), mebfap) Benzothiophenes (e.g., 3-APBT) Indazoles (e.g., AL-38022A) Indenes (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT) MYCO-005 Quinolinylethylamines (e.g., mefloquine)

Scalines	2-Bromomescaline 3-TE 3-TM 4-Desoxymescaline (DESOXY) 4-TE 4-TM Allylescaline Beta-D Cyclopropylmescaline Difluoroescaline Difluoromescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline (3,4,5-TMPEA) Metaescaline Methallylescaline NBOMe-escaline NBOMe-mescaline Proscaline Thioproscaline Tomscaline Trifluoroescaline Trifluoromescaline
2C-x	2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-P 2C-SE 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 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 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x: 2C-O 2C-O-2 2C-O-4 Others: 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOH-2C-B) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CD-2-ETO, 2CD-5-ETO, 2CE-5-ETO, 2CE-5iPrO, 2CT2-5-ETO)
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA
DOx	DOB DOC DOEF DOET DOI DOiPR DOM DON DOPR DOTFM Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: Ganeshas (G-x) (e.g., Ganesha (G, G-1)
4C-x	4C-B 4C-C 4C-D (Ariadne) 4C-E 4C-I 4C-N 4C-P 4C-T-2
MDxx	5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA IDA Lophophine (MMDPEA) Lys-MDA Lys-MDMA MDA (tenamfetamine) MDHMA MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDMA N-t-BOC-MDMA (R)-MDMA
FLY	2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY TFMFly
25x-NB (NBOMes)	25x-NBOMe: 25B-NBOMe • 25C-NBOMe • 25CN-NBOMe • 25D-NBOMe • 25E-NBOMe • 25H-NBOMe • 25I-NBOMe • 25N-NBOMe • 25P-NBOMe • 25T2-NBOMe • 25T4-NBOMe • 25T7-NBOMe • 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25I-NBOH 25P-NBOH Others: 25B-NB (N-benzyl-2C-B) 2CBCB-NBOMe 2CBFly-NBOMe NBOMe-mescaline
Others	2-TOET 2-TOM 4-HA 5-TOET 5-TOM Benzofurans (e.g., F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) TMAs (e.g., TMA-3, TMA-4, TMA-5, TMA-6) TOMSO ZDCM-04 Structure undisclosed: ASR-2001 CYB005
Cyclized	1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 2-Aminotetralins (e.g., DOM-AT) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzazepines (e.g., lorcaserin) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Glaucine IHCH-7113 Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenylmorpholines (phenmetrazines) (e.g., 2C-B-morpholine) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Z3517967757 ZC-B