2C-T-7

Last updated

2C-T-7
2C-T-7 2DACS.svg
2C-T-7-3d-sticks.png
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 class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action 8–15 hours [1]
Identifiers
  • 2-[2,5-dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H21NO2S
Molar mass 255.38 g·mol−1
3D model (JSmol)
Melting point 206 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 Yes check.svgY
  • Key:OLEVEPDJOFPJTF-UHFFFAOYSA-N Yes check.svgY
   (verify)

2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine or as Blue Mystic or 7th Heaven, is a psychedelic drug of the phenethylamine and 2C families. [1] [2] [3] [4] It is taken orally. [1]

Contents

2C-T-7 was first described in the scientific literature by Myron Stolaroff in 1990. [5] It was developed by Alexander Shulgin and colleagues and was described in greater detail by them in 1991, including in Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved). [5] [6] [1]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2C-T-7's dose range as 10 to 30 mg orally and its duration as 8 to 15 hours. [1] It produces psychedelic effects. [1] [5] [7] [8] In PiHKAL, Shulgin records that the hallucinations 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 with mescaline, 2C-B, and 2C-T-2. [1]

Interactions

2C-T-7 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. [10] [11] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-7. [10] [11] [12] This may result in overdose and serious toxicity. [12] [10]

Toxicity and deaths

There have been at least three reported deaths related to 2C-T-7 use as of August 2007, mainly at insufflated (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 website disinfo.com challenged the accuracy of much of the reporting in the aforementioned Rolling Stone article. [18] 2C-T-7 has since been officially made illegal and declared a schedule 1 substance in the United States. [19]

The Partnership 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 as ephedrine and/or MDMA.

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 as ephedrine or MDMA (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

Pharmacodynamics

2C-T-7 activities
Target Affinity (Ki, nM)
5-HT1A 520–878
5-HT1B ND
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 5.3–6.5 (Ki)
1.2–130 (EC50 Tooltip half-maximal effective concentration)
49–101% (Emax Tooltip maximal efficacy)
5-HT2B ND (Ki)
52–350 (EC50)
45–46% (Emax)
5-HT2C 39–54 (Ki)
ND (EC50)
ND (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A 13,000
α1B, α1D ND
α2A 180–335
α2B, α2C ND
β1–β3 ND
D1 15,000
D2 5,000
D3 7,500
D4, D5 ND
H1 >25,000
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1 Tooltip 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)
SERT Tooltip Serotonin transporter12,000 (Ki)
44,000 (IC50 Tooltip half-maximal inhibitory concentration)
ND (EC50)
NET Tooltip Norepinephrine transporter27,000 (Ki)
135,000 (IC50)
ND (EC50)
DAT Tooltip Dopamine transporter34,000 (Ki)
261,000 (IC50)
ND (EC50)
MAO-A Tooltip Monoamine oxidase A46,000 (IC50)
MAO-B Tooltip 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 a 5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by most currently-known hallucinogenic tryptamines and phenethylamines. [29] 2C-T-7 has structural and pharmacodynamic properties similar to those of 2C-T-2. [1]

Chemistry

Synthesis

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

History

2C-T-7 was first described in the scientific literature by Myron Stolaroff by 1990. [5] It was developed by Alexander Shulgin and Peyton Jacob III. [5] [6] [1] Subsequently, 2C-T-7 was described in greater detail by Shulgin and colleagues in 1991. [6] [1]

Up until Operation 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 Japanese smartshops and online. [3] [4]

Society and culture

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

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

Canada

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

China

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

Finland

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

Germany

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

Netherlands

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 the Opium Law.

Sweden

Schedule I in Sweden. [33] 2C-T-7 was first classified 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 April 1, 1999, under SFS 1999:58 [34] that made it illegal to sell or possess.

United Kingdom

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

United States

On September 20, 2002, 2C-T-7 was classified as a Schedule I substance in the United States by an emergency ruling by the DEA. 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 in Las Vegas, Nevada. [19]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 Shulgin A. "PIHKAL #43".
  2. 1 2 Shulgin 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. 1 2 Platoni 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. 1 2 O'Connell C (August 19, 2002). "A psychedelic summer". Newsweek.
  5. 1 2 3 4 5 Clifford 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. 1 2 3 Shulgin 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 from the 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. Retrieved October 30, 2023.
  8. ↑ "Erowid 2C-T-7 Vault: Sulfurous Samadhi: Stolaroff's & Well's Study". erowid.org. February 6, 2001. Retrieved October 30, 2023.
  9. ↑ Shulgin A (June 28, 2001). "2C-T-7". Ask Dr Shulgin. Centre for Cognitive Liberty and Ethics (COLE). Retrieved August 28, 2009.
  10. 1 2 3 Dean 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. 1 2 Theobald 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. 1 2 Halman 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 to Rolling 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 from the 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 from the original on September 8, 2008. Retrieved November 10, 2008.
  19. 1 2 3 "2,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE (Street Names: 2C-T-7, Blue Mystic, T7, Beautiful, Tripstay, Tweety-Bird Mescaline)" (PDF). Retrieved September 3, 2024.
  20. ↑ America PF. "2C-B, 2C-T-7". Archived from the original on October 19, 2006. Retrieved October 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. Retrieved May 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 from the 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. 1 2 Fantegrossi 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 from the original on October 1, 2015. Retrieved October 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 from the original on October 4, 2013. Retrieved September 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 from the original on August 27, 2009. Retrieved July 7, 2008.
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