2C-T-4
Template:Cs1 config Template:Main other <templatestyles src="Infobox drug/styles.css"/> {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0
|preview=
}}{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =
| _has_physiological_data= | _has_gene_therapy=
| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=132112CC(C)Sc1cc(OC)c(cc1OC)CCN1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3HDYZSVKZKDPLDT-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data= Oral<ref name="CitePiHKAL" />Serotonin; 5-HT2 receptor agonist; Serotonergic psychedelic; HallucinogenNone | _legal_data=
| _other_data=2-{2,5-Dimethoxy-4-[(propan-2-yl)sulfanyl]phenyl}ethan-1-amine
| _image_0_or_2 = 2C-T-4 2DACS.svg2C-T-4-3d-sticks.png | _image_LR =
| _datapage = 2C-T-4 (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all= | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=207740-25-8 | PubChem=44350070 | ChemSpiderID=21106232 | ChEBI= | ChEMBL=338259 | DrugBank= | KEGG=C22735 | _hasInChI_or_Key={{#if:1S/C13H21NO2S/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3HDYZSVKZKDPLDT-UHFFFAOYSA-N |yes}} | UNII=558WSD71D4 | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields=changed |Watchedfields=changed |verifiedrevid=477216693}}
2C-T-4, also known as 4-isopropylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family.<ref name="CitePiHKAL" /><ref name="ShulginManningDaley2011">Template:Cite book</ref> It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.<ref name="CitePiHKAL" />
EffectsEdit
2C-T-4 produces psychedelic and entheogenic effects that develop slowly and can last 12 to 18Template:Nbsphours.<ref name="CitePiHKAL" /> While users may experience virtually no effects for the first hour after ingestion, results vary drastically between individuals and range from hallucination and euphoria to intense sickness and anxiety.<ref name="CitePiHKAL">Template:CitePiHKAL</ref> Shulgin devoted a chapter in the first part of his book PiHKAL to this compound, describing an intense "plus-four" psychedelic experience mediated by a twelve milligram dose.
InteractionsEdit
2C drugs are metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.<ref name="DeanStellpflugBurnett2013">Template:Cite journal</ref><ref name="TheobaldMaurer2007">Template:Cite journal</ref> Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C drugs.<ref name="DeanStellpflugBurnett2013" /><ref name="TheobaldMaurer2007" /><ref name="HalmanKongSarris2024">Template:Cite journal</ref> This may result in overdose and serious toxicity.<ref name="HalmanKongSarris2024" /><ref name="DeanStellpflugBurnett2013" />
PharmacologyEdit
2C-T-4 acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.<ref name="LuethiTrachselHoener2018" /><ref name="RickliLuethiReinisch2015" /> The mechanism that produces 2C-T-4's hallucinogenic and entheogenic effects has not been specifically established, however it is most likely to result from 5-HT2A receptor activation in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines for which the mechanism of action is known.
ChemistryEdit
2C-T-4 is the 2-carbon homolog of Aleph-4. The full chemical name is 2-[4-(isopropylthio)-2,5-dimethoxyphenyl]-ethanamine. The drug has structural and pharmacodynamic properties similar to 2C-T-7 and 2C-T-19.Template:Citation needed
HomologueEdit
2C-T-4 has a homologue, the structural isomer Ψ-2C-T-4 (2,6-dimethoxy-4-(i)-propylthiophenethylamine). This compound was tested by Alexander Shulgin at a dose of 12 mg.
At this dosage its duration was very short and it produced few effects, however based on the research into the better characterized compound Ψ-DOM, the potency of Ψ-2C-T-4 is likely to be around 1/3 that of 2C-T-4 itself, so a more effective dosage of Ψ-2C-T-4 might be in the region of 20–60 mg;<ref name="CitePiHKAL"/> however high doses such as this might well be associated with toxic side effects, and so extreme caution would be advised.
Society and cultureEdit
PopularityEdit
2C-T-4 is relatively unknown on the black market, but has been sold to a limited extent on the research chemical market.Template:Citation needed
Legal statusEdit
CanadaEdit
As of October 31, 2016, 2C-T-4 is a controlled substance (Schedule III) in Canada.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
ChinaEdit
As of October 2015 2C-T-4 is a controlled substance in China.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
DenmarkEdit
2C-T-4 is added to the list of Schedule B controlled substances.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
SwedenEdit
Sveriges riksdags health ministry Statens folkhälsoinstitut classified 2C-T-4 as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Jul 15, 2007, in their regulation SFS 2007:600 listed as 2,5-dimetoxi-4-isopropyltiofenetylamin (2C-T-4), making it illegal to sell or possess.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
United StatesEdit
As of July 9, 2012, 2C-T-4 is a Schedule I substance in the United States, under the Synthetic Drug Abuse Prevention Act of 2012.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>
ReferencesEdit
External linksEdit
- 2C-T-4 - Isomer Design
- 2C-T-4 - Erowid
- The Big & Dandy 2C-T-4 Thread - Bluelight
- 2C-T-4 - PiHKAL - Erowid
- 2C-T-4 - PiHKAL - Isomer Design
Template:Psychedelics Template:Serotonin receptor modulators Template:TAAR modulators {{#invoke:Navbox|navbox}}