2C-T-7
{{Short description|Psychedelic phenthylamine drug}}
{{Use mdy dates|date=June 2013}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 477216761
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| image = 2C-T-7 2DACS.svg
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| image2 = 2C-T-7-3d-sticks.png
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| routes_of_administration = Oral
| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
| ATC_suffix =
| legal_BR = F2
| legal_CA = Schedule III
| legal_DE =
| legal_US = Schedule I
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| duration_of_action = 8–15 hours
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 207740-26-9
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| PubChem = 24728635
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106233
| UNII = TJG366J9BA
| KEGG = C22737
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 126432
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| synonyms = 2,5-Dimethoxy-4-propylthiophenethylamine; 2,5-Dimethoxy-4-propylsulfanylphenethylamine; 4-Propylthio-2,5-dimethoxyphenethylamine; 4-Propylsulfanyl-2,5-dimethoxyphenethylamine; Blue Mystic; Tweety-Bird Mescaline
| IUPAC_name = 2-[2,5-dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine
| C=13 | H=21 | N=1 | O=2 | S=1
| SMILES = COc1cc(SCCC)c(cc1CCN)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OLEVEPDJOFPJTF-UHFFFAOYSA-N
| melting_point = 206
| melting_high = 207
| melting_notes =
}}
2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10–30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours.{{cite web|url=http://www.erowid.org/library/books_online/pihkal/pihkal043.shtml |title=PIHKAL #43 | vauthors = Shulgin A }}
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. It has been known on the streets as Blue Mystic or 7th Heaven.{{cite news | vauthors = Platoni K | title = 2C-T-7's Bad Trip | publisher = East Bay Express | date = May 1, 2002 | quote = 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}}{{cite web | vauthors = O'Connell C | title = A psychedelic summer | publisher = Newsweek | date = August 19, 2002 | url = http://www.newsweek.com/id/65381?tid=relatedcl}}
There has been little real research done on this chemical other than Shulgin's comments in PiHKAL and a few small animal studies mostly aimed at detecting metabolites.
Effects
2C-T-7 is psychedelic.{{Cite web | vauthors = Hardison C |date=2000 |title=An Amateur Qualitative Study of 48 2C-T-7 Subjective Bioassays |url=https://maps.org/news-letters/v10n2/10211har.html |access-date=2023-10-30 |website=maps.org |publisher=Bulletin of the Multidisciplinary Association for Psychedelic Studies MAPS}}{{Cite web |date=2001-02-06 |title=Erowid 2C-T-7 Vault: Sulfurous Samadhi: Stolaroff's & Well's Study |url= https://erowid.org/chemicals/2ct7/article1/stolaroff.shtml |access-date=2023-10-30 |website=erowid.org}} In PiHKAL, Shulgin records that the hallucinations are unique, and that the chemical may cause muscle tension and an altered vocal quality.{{cite web | vauthors = Shulgin A | author-link =Alexander Shulgin | title =2C-T-7 | work =Ask Dr Shulgin | publisher =Centre for Cognitive Liberty and Ethics (COLE) | date =June 28, 2001 | url =http://www.cognitiveliberty.org/shulgin/adsarchive/2ct7.htm | access-date =August 28, 2009 }} Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamine compounds, together with mescaline, 2C-B, and 2C-T-2.{{Cite web | vauthors = Shulgin A |date=1990 |title="PIHKAL" - The Chemical Story |url=https://www.erowid.org/library/books_online/pihkal/pihkal.shtml |access-date=2023-10-30 |website=www.erowid.org}}
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
2C-T-7 is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B.{{cite journal | vauthors = Dean BV, Stellpflug SJ, Burnett AM, Engebretsen KM | title = 2C or not 2C: phenethylamine designer drug review | journal = J Med Toxicol | volume = 9 | issue = 2 | pages = 172–178 | date = June 2013 | pmid = 23494844 | pmc = 3657019 | doi = 10.1007/s13181-013-0295-x | url = }}{{cite journal | vauthors = Theobald DS, Maurer HH | title = Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series) | journal = Biochem Pharmacol | volume = 73 | issue = 2 | pages = 287–297 | date = January 2007 | pmid = 17067556 | doi = 10.1016/j.bcp.2006.09.022 | url = }} Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-T-7.{{Cite journal |vauthors=Halman A, Kong G, Sarris J, Perkins D |date=January 2024 |title=Drug-drug interactions involving classic psychedelics: A systematic review |journal=J Psychopharmacol |volume=38 |issue=1 |pages=3–18 |doi=10.1177/02698811231211219 |pmc=10851641 |pmid=37982394}} This may result in overdose and serious toxicity.
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.{{cite journal | vauthors = Curtis B, Kemp P, Harty L, Choi C, Christensen D | title = Postmortem identification and quantitation of 2,5-dimethoxy-4-n-propylthiophenethylamine using GC-MSD and GC-NPD | journal = Journal of Analytical Toxicology | volume = 27 | issue = 7 | pages = 493–8 | date = October 2003 | pmid = 14607005 | doi = 10.1093/jat/27.7.493 | quote = 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. }}{{cite report | vauthors = Platoni C | title = A psychedelic summer | work = East Bay Express | date = 1 May 2002 | quote = 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}} 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.{{cite web | title = 2,5-dimethoxy-4-(n)-propylthiophenethylamine | work = Drugs and Chemicals of Concern | publisher = Office of Diversion Control, Drug Enforcement Administration, U.S. Department of Justice | url = http://www.deadiversion.usdoj.gov/drugs_concern/2ct7.htm | archive-url=https://web.archive.org/web/20081020211953/http://www.deadiversion.usdoj.gov/drugs_concern/2ct7.htm | archive-date=October 20, 2008 }}
In January 2002, Rolling Stone published an article about 2C-T-7 entitled "The New (legal) Killer Drug"."The New (Legal) Killer Drug". Rolling Stone, January 10, 2002, issue 888: 44–49. 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. 21 USC §813 A detailed response on the website disinfo.com challenged the accuracy of much of the reporting in the aforementioned Rolling Stone article.{{cite web | title = The new (hip) drug hysteria: a journey into rolling stone's abandonment of journalistic ethics | vauthors = Lilly K | publisher = Disinformation | date = 2002 | url = http://www.disinfo.com/archive/pages/article/id2071/pg1/index.html | access-date = November 10, 2008 | archive-url = https://web.archive.org/web/20080908005322/http://www.disinfo.com/archive/pages/article/id2071/pg1/index.html | archive-date = September 8, 2008 | url-status = dead }} 2C-T-7 has since been officially made illegal and declared a schedule 1 substance in the United States.
The Partnership for a Drug-Free America reported in 2006 that 2C-T-7 can be lethal even in small doses;{{cite web|url=http://www.drugfree.org/Portal/Drug_guide/2C-B_2C-T-7|title=2C-B, 2C-T-7|author=Partnership for a Drug-Free America|author-link=Partnership for a Drug-Free America|access-date=October 4, 2006|archive-url=https://web.archive.org/web/20061019162712/http://www.drugfree.org/Portal/drug_guide/2C-B_2C-T-7|archive-date=October 19, 2006|url-status=dead}} 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){{cite journal | vauthors = Baldessarini RJ | title = Symposium: behavior modification by drugs. I. Pharmacology of the amphetamines | journal = Pediatrics | volume = 49 | issue = 5 | pages = 694–701 | date = May 1972 | pmid = 4338459 | doi = 10.1542/peds.49.5.694 | s2cid = 245067669 }} 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 US DEA.
Pharmacology
The mechanism that produces the psychedelic and entactogenic 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.{{cite journal | vauthors = Fantegrossi WE, Harrington AW, Eckler JR, Arshad S, Rabin RA, Winter JC, Coop A, Rice KC, Woods JH | title = Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats | journal = Psychopharmacology | volume = 181 | issue = 3 | pages = 496–503 | date = September 2005 | pmid = 15983786 | doi = 10.1007/s00213-005-0009-4 | hdl-access = free | s2cid = 8108926 | hdl = 2027.42/46369 | url = https://deepblue.lib.umich.edu/bitstream/handle/2027.42/46369/213_2005_Article_9.pdf}} 2C-T-7 has structural and pharmacodynamic properties similar to those of 2C-T-2.
Society and culture
=Legal status=
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==
==Canada==
As of October 31, 2016, 2C-T-7 is a controlled substance (Schedule III) in Canada.{{cite web |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title=Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|first=((Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada)) |last=Gazette |website=gazette.gc.ca|date=2016-05-04}}
==China==
As of October 2015 2C-T-7 is a controlled substance in China.{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=October 1, 2015 | url-status=dead }}
==Germany==
2C-T-7 is scheduled in Germany. (BTMG)
==The 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.{{cite web | url = http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf | title = Läkemedelsverkets författningssamling}} 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{{cite web|url=http://www.notisum.se/rnp/sls/fakta/a9990058.HTM|title=Förordning (1999:58) om förbud mot vissa hälsofarliga varor - Karnov Open|website=notisum.se|access-date=September 15, 2013|archive-date=October 4, 2013|archive-url=https://web.archive.org/web/20131004215233/http://www.notisum.se/rnp/sls/fakta/a9990058.HTM|url-status=dead}} 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|date=September 2016}}
==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){{cite web|url=http://www.usdoj.gov/ndic/pubs11/12207/12207p.pdf|title=2C-T-7 Fast Facts|author=U.S. Department of Justice}}{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=List of Schedule 1 drugs on the DEA Office of Diversion Control website |access-date=July 7, 2008 |archive-date=August 27, 2009 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }}
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.{{cite web | title=2,5-DIMETHOXY-4-(n)-PROPYLTHIOPHENETHYLAMINE (Street Names: 2C-T-7, Blue Mystic, T7, Beautiful, Tripstay, Tweety-Bird Mescaline) | url=https://www.deadiversion.usdoj.gov/drug_chem_info/2ct7.pdf | access-date=3 Sep 2024}}
References
{{Reflist}}
External links
- [https://isomerdesign.com/pihkal/explore/43 2C-T-7 - Isomer Design]
- [https://psychonautwiki.org/wiki/2C-T-7 2C-T-7 - PsychonautWiki]
- [http://erowid.org/chemicals/2ct7/ 2C-T-7 - Erowid]
- [http://www.erowid.org/library/books_online/pihkal/pihkal043.shtml 2C-T-7 - PiHKAL - Erowid]
- [http://pihkal.info/read.php?domain=pk&id=43 2C-T-7 - PiHKAL - Isomer Design]
- [https://tripsitter.com/2ct7/ 2C-T-7: A Mixed Bag of Psychedelic Tricks - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}