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2C-T-7

From Wikipedia, the free encyclopedia
Psychedelic phenthylamine drug

Pharmaceutical compound
2C-T-7
Clinical data
Other names2,5-Dimethoxy-4-propylthiophenethylamine; 2,5-Dimethoxy-4-propylsulfanylphenethylamine; 4-Propylthio-2,5-dimethoxyphenethylamine; 4-Propylsulfanyl-2,5-dimethoxyphenethylamine; Blue Mystic; Tweety-Bird Mescaline
Routes of
administration
Oral[1]
Drug classSerotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action8–15 hours[1]
Identifiers
  • 2-[2,5-dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H21NO2S
Molar mass255.38 g·mol−1
3D model (JSmol)
Melting point206 to 207 °C (403 to 405 °F)
  • COc1cc(SCCC)c(cc1CCN)OC
  • InChI=1S/C13H21NO2S/c1-4-7-17-13-9-11(15-2)10(5-6-14)8-12(13)16-3/h8-9H,4-7,14H2,1-3H3 checkY
  • Key:OLEVEPDJOFPJTF-UHFFFAOYSA-N checkY
  (verify)

2C-T-7, also known as4-propylthio-2,5-dimethoxyphenethylamine or asBlue Mystic or7th Heaven, is apsychedelic drug of thephenethylamine and2C families.[1][2][3][4] It is takenorally.[1]

2C-T-7 was first described in thescientific literature byMyron Stolaroff in 1990.[5] It was developed byAlexander Shulgin and colleagues and was described in greater detail by them in 1991, including in Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved).[5][6][1]

Use and effects

[edit]

In his bookPiHKAL (Phenethylamines I Have Known and Loved),Alexander Shulgin lists 2C-T-7's dose range as 10 to 30 mgorally and itsduration as 8 to 15 hours.[1] It producespsychedelic effects.[1][5][7][8] InPiHKAL, Shulgin records that thehallucinations it produces are unique, and that the chemical may cause muscle tension and an altered vocal quality.[9] Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamines, together withmescaline,2C-B, and2C-T-2.[1]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

2C-T-7 ismetabolized by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.[10][11]Monoamine oxidase inhibitors (MAOIs) such asphenelzine,tranylcypromine,moclobemide, andselegiline may potentiate the effects of 2C-T-7.[10][11][12] This may result inoverdose and serioustoxicity.[12][10]

Toxicity and deaths

[edit]

There have been at least three reported deaths related to 2C-T-7 use as of August 2007, mainly atinsufflated (snorted) doses of 30 mg or more.[13][14] In the fall of 2000, a young healthy male died following insufflation of an excessive amount of 2C-T-7. Two additional deaths reported in April 2001 have been linked to 2C-T-7. These two deaths were reported by the DEA as being the result of the co-abuse of 2C-T-7 with MDMA.[15]

In January 2002,Rolling Stone published an article about 2C-T-7 entitled "The New (legal) Killer Drug".[16] Although the article suggested that the drug was legal, the legal status of 2C-T-7 was ambiguous at the time due to the United States'Federal Analogue Act.[17] A detailed response on the websitedisinfo.com challenged the accuracy of much of the reporting in the aforementionedRolling Stone article.[18] 2C-T-7 has since been officially made illegal and declared a schedule 1 substance in the United States.[19]

ThePartnership for a Drug-Free America reported in 2006 that 2C-T-7 can be lethal even in small doses;[20] however, they provide no source for their claim and of the three known deaths (as of August 2007) of 2C-T-7 intoxicated individuals, all involved either uncommonly large insufflated doses or the concomitant ingestion of other stimulants such asephedrine and/orMDMA.

All of the three aforementioned known deaths of individuals under the influence of 2C-T-7 occurred in those known to be either intoxicated with other stimulants such asephedrine orMDMA (which are known to be potentially lethal in certain situations or at excessive doses)[21] or after the individual insufflated an amount of 2C-T-7 much greater than necessary to induce the full range of effects typically sought after by users of the drug; for example, the reported 35 mg insufflated dose taken by the individual who died in the fall of 2000. This reported dose was characterized as "excessive" by the United States DEA.

Pharmacology

[edit]

Pharmacodynamics

[edit]
2C-T-7 activities
TargetAffinity (Ki, nM)
5-HT1A520–878
5-HT1BND
5-HT1DND
5-HT1END
5-HT1FND
5-HT2A5.3–6.5 (Ki)
1.2–130 (EC50Tooltip half-maximal effective concentration)
49–101% (EmaxTooltip maximal efficacy)
5-HT2BND (Ki)
52–350 (
EC50)
45–46% (
Emax)
5-HT2C39–54 (Ki)
ND (EC50)
ND (Emax)
5-HT3ND
5-HT4ND
5-HT5AND
5-HT6ND
5-HT7ND
α1A13,000
α1B,α1DND
α2A180–335
α2B,α2CND
β1β3ND
D115,000
D25,000
D37,500
D4,D5ND
H1>25,000
H2H4ND
M1M5ND
I1ND
σ1,σ2ND
TAAR1Tooltip Trace amine-associated receptor 1311–560 (Ki) (mouse)
10–33 (Ki) (rat)
910 (EC50) (mouse)
79 (
EC50) (rat)
>30,000 (
EC50) (human)
67% (
Emax) (mouse)
83% (
Emax) (rat)
SERTTooltip Serotonin transporter12,000 (Ki)
44,000 (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter27,000 (Ki)
135,000 (IC50)
ND (EC50)
DATTooltip Dopamine transporter34,000 (Ki)
261,000 (IC50)
ND (EC50)
MAO-ATooltip Monoamine oxidase A46,000 (IC50)
MAO-BTooltip Monoamine oxidase B180,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs:[22][23][24][25][26][27][28][29]

The mechanism that produces the psychedelic effects of 2C-T-7 is most likely to result from action as a5-HT2Aserotonin receptoragonist in the brain, a mechanism of action shared by most currently-known hallucinogenictryptamines andphenethylamines.[29] 2C-T-7 has structural and pharmacodynamic properties similar to those of2C-T-2.[1]

Chemistry

[edit]

Synthesis

[edit]

Thechemical synthesis of 2C-T-7 has been described.[1][2]

History

[edit]

2C-T-7 was first described in thescientific literature byMyron Stolaroff by 1990.[5] It was developed byAlexander Shulgin andPeyton Jacob III.[5][6][1] Subsequently, 2C-T-7 was described in greater detail by Shulgin and colleagues in 1991.[6][1]

Up untilOperation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanesesmartshops and online.[3][4]

Society and culture

[edit]

Legal status

[edit]

Around the year 2000, 2C-T-7 began to change from an obscure chemical to a drug used at parties and clubs in North America and Europe as it became available through a number of grey-market commercial vendors. This aroused the attention of the authorities, and many countries have since scheduled the chemical.

Australia

[edit]

In Australia,2C-T-2 and 2C-T-7 are covered by the country'sanalogue drug laws.

Canada

[edit]

As of October 31, 2016, 2C-T-7 is a controlled substance (Schedule III) in Canada.[30]

China

[edit]

As of October 2015 2C-T-7 is a controlled substance in China.[31]

Finland

[edit]

2C-T-7 is scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs".[32]

Germany

[edit]

2C-T-7 is scheduled in Germany. (BTMG)

Netherlands

[edit]

The Netherlands was the first country in the world to ban 2C-T-7, after being sold in smartshops for a short period. After 2C-T-2 was first banned, 2C-T-7 quickly appeared on the market, but was soon banned as well. 2C-T-7 is a list I drug of theOpium Law.

Sweden

[edit]

Schedule I in Sweden.[33] 2C-T-7 was first classified as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varor (translatedAct on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58[34] that made it illegal to sell or possess.

United Kingdom

[edit]

In 1999,Alexander Shulgin was sent a copy of a letter from theBritish Home Office to several of its administrative associates that in effect placed all compounds listed inPiHKAL into Class A.[citation needed]

United States

[edit]

On September 20, 2002, 2C-T-7 was classified as aSchedule I substance in the United States by an emergency ruling by theDEA. On March 18, 2004, the DEA published a Final Rule in the Federal Register permanently placing 2C-T-7 in Schedule I. (69 FR 12794)[19][35][36]

As of April 2024, law enforcement have encountered 2C-T-7 in 16 states, with the highest number of encounters being in Florida. Purchases made over the internet are believed by the DEA to be the most common source by which users of the drug acquire it in the United States, and one laboratory manufacturing the drug was discovered by police inLas Vegas, Nevada.[19]

See also

[edit]

References

[edit]
  1. ^abcdefghijklShulgin A."PIHKAL #43".
  2. ^abShulgin A, Manning T, Daley P (2011).The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley:Transform Press.ISBN 978-0-9630096-3-0.
  3. ^abPlatoni K (May 1, 2002). "2C-T-7's Bad Trip". East Bay Express.In 1999 it made its first commercial appearance in the Netherlands' drug-dealing smart shops in both tablet and powder form. It was given the street name "Blue Mystic," perhaps in order to differentiate it from its chemical cousin, another Shulgin creation named 2C-T-2
  4. ^abO'Connell C (August 19, 2002)."A psychedelic summer". Newsweek.
  5. ^abcdeClifford JS, Baldwin N, Brett J, Cerbo L, Demers-Gendreau C (July 1, 1990). "Treatment of alcoholism".Journal of Psychoactive Drugs.22 (3): 377.doi:10.1080/02791072.1990.10472568.PMID 2286872.
  6. ^abcShulgin AT, Shulgin A, Jacob P (January 1991)."Central nervous system (CNS) activity of two new psychoactive compounds".Journal of Psychoactive Drugs.23 (1):95–96.doi:10.1080/02791072.1991.10472583.eISSN 2159-9777.PMID 1941371. Archived fromthe original on July 13, 2025.
  7. ^Hardison C (2000)."An Amateur Qualitative Study of 48 2C-T-7 Subjective Bioassays".maps.org. Bulletin of the Multidisciplinary Association for Psychedelic Studies MAPS. RetrievedOctober 30, 2023.
  8. ^"Erowid 2C-T-7 Vault: Sulfurous Samadhi: Stolaroff's & Well's Study".erowid.org. February 6, 2001. RetrievedOctober 30, 2023.
  9. ^Shulgin A (June 28, 2001)."2C-T-7".Ask Dr Shulgin. Centre for Cognitive Liberty and Ethics (COLE). RetrievedAugust 28, 2009.
  10. ^abcDean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013)."2C or not 2C: phenethylamine designer drug review".Journal of Medical Toxicology.9 (2):172–178.doi:10.1007/s13181-013-0295-x.PMC 3657019.PMID 23494844.
  11. ^abTheobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)".Biochemical Pharmacology.73 (2):287–297.doi:10.1016/j.bcp.2006.09.022.PMID 17067556.
  12. ^abHalman A, Kong G, Sarris J, Perkins D (January 2024)."Drug-drug interactions involving classic psychedelics: A systematic review".Journal of Psychopharmacology.38 (1):3–18.doi:10.1177/02698811231211219.PMC 10851641.PMID 37982394.
  13. ^Curtis B, Kemp P, Harty L, Choi C, Christensen D (October 2003). "Postmortem identification and quantitation of 2,5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD".Journal of Analytical Toxicology.27 (7):493–498.doi:10.1093/jat/27.7.493.PMID 14607005.This compound was initially identified from a routine screening procedure in postmortem urine from a 20-year-old male that died in a local emergency room after reportedly insufflating 35 mg.
  14. ^Platoni C (May 1, 2002). A psychedelic summer.East Bay Express (Report).In the same month, Joshua Robbins, a seventeen-year-old from Cordova, Tennessee, died after snorting between thirty and thirty-five milligrams of 2C-T-7, not long after taking several other stimulant drugs. According toRolling Stone, which ran an article on Robbins' death, in the twelve hours before he died Robbins also had consumed Ecstasy, nitrous oxide, and a 'mini-thin' containing ephedrine and guaifenisen or combined with stimulants such as MDMA
  15. ^"2,5-dimethoxy-4-(n)-propylthiophenethylamine".Drugs and Chemicals of Concern. Office of Diversion Control, Drug Enforcement Administration, U.S. Department of Justice. Archived fromthe original on October 20, 2008.
  16. ^"The New (Legal) Killer Drug".Rolling Stone, January 10, 2002, issue 888: 44–49.
  17. ^21 USC §813
  18. ^Lilly K (2002)."The new (hip) drug hysteria: a journey into rolling stone's abandonment of journalistic ethics". Disinformation. Archived fromthe original on September 8, 2008. RetrievedNovember 10, 2008.
  19. ^abc"2,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE (Street Names: 2C-T-7, Blue Mystic, T7, Beautiful, Tripstay, Tweety-Bird Mescaline)"(PDF). RetrievedSeptember 3, 2024.
  20. ^America PF."2C-B, 2C-T-7". Archived fromthe original on October 19, 2006. RetrievedOctober 4, 2006.
  21. ^Baldessarini RJ (May 1972). "Symposium: behavior modification by drugs. I. Pharmacology of the amphetamines".Pediatrics.49 (5):694–701.doi:10.1542/peds.49.5.694.PMID 4338459.S2CID 245067669.
  22. ^"Kᵢ Database".PDSP. May 10, 2025. RetrievedMay 10, 2025.
  23. ^Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)".Neuropharmacology.99:546–553.doi:10.1016/j.neuropharm.2015.08.034.PMID 26318099.
  24. ^Luethi D, Trachsel D, Hoener MC, Liechti ME (May 2018). "Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs)".Neuropharmacology.134 (Pt A):141–148.doi:10.1016/j.neuropharm.2017.07.012.PMID 28720478.
  25. ^Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor".Archives of Toxicology.94 (10):3449–3460.Bibcode:2020ArTox..94.3449P.doi:10.1007/s00204-020-02836-w.hdl:1854/LU-8687071.PMID 32627074.
  26. ^Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases".Drug Testing and Analysis.11 (2):318–324.doi:10.1002/dta.2494.PMID 30188017.
  27. ^Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016)."In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1"(PDF).The Journal of Pharmacology and Experimental Therapeutics.357 (1):134–144.doi:10.1124/jpet.115.229765.PMID 26791601. Archived fromthe original(PDF) on May 9, 2025.
  28. ^Fantegrossi WE, Murnane KS, Reissig CJ (January 2008)."The behavioral pharmacology of hallucinogens".Biochemical Pharmacology.75 (1):17–33.doi:10.1016/j.bcp.2007.07.018.PMC 2247373.PMID 17977517.
  29. ^abFantegrossi WE, Harrington AW, Eckler JR, Arshad S, Rabin RA, Winter JC, et al. (September 2005). "Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats".Psychopharmacology.181 (3):496–503.doi:10.1007/s00213-005-0009-4.hdl:2027.42/46369.PMID 15983786.S2CID 8108926.
  30. ^"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)".Gazette. Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada. May 4, 2016.
  31. ^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. September 27, 2015. Archived fromthe original on October 1, 2015. RetrievedOctober 1, 2015.
  32. ^"Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista | 543/2008 | Lainsäädäntö | Finlex".
  33. ^"Läkemedelsverkets författningssamling"(PDF).
  34. ^"Förordning (1999:58) om förbud mot vissa hälsofarliga varor - Karnov Open".notisum.se. Archived fromthe original on October 4, 2013. RetrievedSeptember 15, 2013.
  35. ^"2C-T-7 Fast Facts"(PDF). U.S.Department of Justice.
  36. ^"List of Schedule 1 drugs on the DEA Office of Diversion Control website". Archived fromthe original on August 27, 2009. RetrievedJuly 7, 2008.

External links

[edit]
Tryptamines
No ring subs.
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TAAR1Tooltip Trace amine-associated receptor 1
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Inverse agonists
TAAR5Tooltip Trace amine-associated receptor 5
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Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as theList of trace amines,TAAR, andTAAR1 pages.
See also:Receptor/signaling modulators
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