View source for 2C-T-7

{{chembox
| ImageFile1 = 2C-T-7.svg
| ImageSize1 = 300px
| ImageFile2 = 2C-T-7-3d-sticks.png
| ImageSize2 = 200px
| IUPACName = 2-[2,5-Dimethoxy-4-(propylthio)phenyl]ethanamine
| OtherNames = 2,5-Dimethoxy-4-''n''-propylthiophenethylamine
| Section1 = {{Chembox Identifiers
| ChemSpiderID = 21106233
| InChI = 1/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
| InChIKey = OLEVEPDJOFPJTF-UHFFFAOYAR
| CASNo = 207740-26-9
| PubChem =
| SMILES = COc1cc(SCCC)c(cc1CCN)OC
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>13</sub>H<sub>21</sub>NO<sub>2</sub>S
| MolarMass = 255.38 g/mol
| Appearance =
| Density =
| MeltingPt = 140-150 °C at 33.4 Pa
| BoilingPt =
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition = }}
}}
'''2C-T-7''' is a [[psychedelic]] [[phenethylamine]] of the [[2C (psychedelics)|2C family]]. In his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]'', [[Alexander Shulgin]] lists the dosage range as 10 to 30 [[milligram|mg]]. 2C-T-7 is generally taken [[Mouth|orally]], and produces psychedelic and [[entheogen]]ic effects that last 8 to 15 hours.<ref>{{cite web|url=http://www.erowid.org/library/books_online/pihkal/pihkal043.shtml|title=PIHKAL #43|author=Alexander Shulgin}}</ref> Up until [[Operation Web Tryp]] and three deaths, two of which involved the use of other drugs in addition to 2-C-T-7 and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanese [[smartshop]]s and online, it is known on the streets as "Blue Mystic".<ref>Platoni, Kara. "2C-T-7's Bad Trip". East Bay Express May 1, 2002: "In 1999 it made its first commercial appearance in Holland's 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]]"</ref><ref>O'Connell, Chris. "A psychedelic summer". Newsweek Aug. 19 2002: http://www.newsweek.com/id/65381?tid=relatedcl</ref><!-- Please do NOT add more slang terms without providing reliable sources for their importance and widespread use -->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.

==Pharmacology==
The mechanism that produces the psychedelic and entheogenic effects of 2C-T-7 is most likely to result from action as a [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[5-HT receptor|serotonin receptor]] [[agonist]] in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines.<ref>{{cite journal|last=Fantegrossi|first=WE|coauthors=Harrington AW, Eckler JR, Arshad S, Rabin RA, Winter JC, Coop A, Rice KC, Woods JH|year=2005|month=September|volume=181|issue=3|pages=496–503|title=Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats|journal=Psychopharmacology (Berlin)|doi=10.1007/s00213-005-0009-4|pmid=15983786}}</ref>

As the 2,5-desmethoxy derivative of 2C-T-7 has been shown to be a moderate [[monoamine oxidase]]-A inhibitor, 2C-T-7&nbsp;may likewise have MAO-A inhibitory effects. If 2C-T-7 does have MAO-A inhibitory effects, then this could indicate that 2C-T-7 is more likely to induce [[serotonin syndrome]], especially at high dosages, than other serotonergic hallucinogens,<ref>{{cite journal|last=Gallardo-Godoy|first=A|coauthors=Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE.|title=Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling|journal=Journal of Medicinal Chemistry|date=April 7, 2005|volume=48|issue=7|pages=2407–19|doi=10.1021/jm0493109|pmid=15801832}}</ref> which may contribute to the toxic effects of ephedrine and MDMA which have been shown to increase following MAO inhibition. (See: Deaths, infra)

==Effects==
[[Image:Chemical 2ct7.jpg|thumb|right|2C-T-7 HCl]]

2C-T-7 is psychedelic. In PiHKAL, Shulgin writes that the hallucinations are unique. He also comments on the tenseness of his muscles and his change in voice tone, which lasted some days. Shulgin suggested reading about amateur research on 2C-T-7's effects.<ref name="coleads">{{cite web
  | last =Shulgin
  | first =Dr Alexander
| authorlink =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
  | accessdate =August 28, 2009
}}</ref> [[Erowid]] gives the following effects list:
===Positive===
* sense of well-being (enhanced lucidity, sense of inner peace)
* [[emotional]] opening
* significant closed and open eye visuals
* increased appreciation of [[music]]

===Neutral===
* sexual dysfunction
* general change in [[consciousness]] (as with most psychoactives)
* [[pupil]] dilation
* change in perception of [[time]]
* visual hallucinations
* auditory hallucinations

===Negative===
* arrhythmia
* paranoia
* psychotic break
* [[nausea]] and [[vomit]]ing
* muscle tension
* insomnia
* muscle tremors and/or convulsions
* memory loss (at higher doses)
* hallucinations
* delirium (at higher doses) (potentially dangerous)
* violent behaviour (at higher doses)
* tachycardia
* death (when snorted in excess)

The drug can be taken orally or snorted, although nasal administration is reported to be extremely painful.<ref>{{cite web|url=http://www.eastbayexpress.com/issues/2002-05-01/news/feature.html|title=2C-T-7's Bad Trip|author=East Bay Express|date=January 2, 2007}}</ref> Use of 2C-T-7 as a [[nootropic]] at low doses of 1–10&nbsp;mg has been reported, and it may be useful for this purpose in a similar manner to [[LSD]], which shows modest stimulant and nootropic effects at doses of 10&nbsp;µg.

==Deaths==
The [[Partnership for a Drug-Free America]] reports that 2C-T-7 can be lethal even in small doses<ref>{{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|authorlink=Partnership for a Drug-Free America|accessdate=October 4, 2006}}</ref>, however; they provide no source for their claim and of the three known deaths of 2C-T-7 intoxicated individuals, all involved either excessive [[Insufflation (medicine)|insufflated]] doses or the concomitant ingestion of other stimulants such as ephedrine and MDMA. There have been at least three reported deaths related to 2C-T-7 use as of August, 2007, mainly at insufflated doses of 30&nbsp;mg or more<ref>Curtis, B. "Postmortem Identification and Quantitation of 2,5-Dimethoxy-4-n-propylthiophenethylamine Using GC-MSD and GC-NPD." Journal of Analytical Toxicology 27.7 (2003): 493-98:  "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."</ref><ref>Platoni, Chris. "A psychedelic summer". East Bay Express May 1, 2002:  "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."</ref> or combined with stimulants such as [[MDMA]],<ref>"In the fall of 2000, a young healthy male died following snorting an excessive amount of 2C-T-7. Since this initial 2C-T-7-related death, two additional deaths reported in April 2001 have been linked to 2C-T-7. These two deaths resulted from the co-abuse of 2C-T-7 with MDMA." http://www.deadiversion.usdoj.gov/drugs_concern/2ct7.htm</ref> as well as a number of very bad trips and hospitalizations, these mostly followed insufflation of 2C-T-7. In January 2002, ''[[Rolling Stone Magazine|Rolling Stone]]'' published an article about 2C-T-7 entitled "The New (legal) Killer Drug",<ref>"The New (Legal) Killer Drug". Rolling Stone January 10, 2002 issue 888: 44-49.</ref> although the legal status of the drug was misrepresented in the article, as 2C-T-7 was already illegal under the United States' analog act.<ref>21 USC §813</ref> A detailed response on the website Disinformation challenged the accuracy of much of the reporting in that ''Rolling Stone'' article.<ref>"the new (hip) drug hysteria: a journey into rolling stone's abandonment of journalistic ethics" by Ken Lilly on Disinformation (2002): http://www.disinfo.com/archive/pages/article/id2071/pg1/index.html</ref>

All of these known deaths of individuals under the influence of 2C-T-7, therefore, occurred in those known either to be intoxicated with potentially deadly<ref>Baldessarini M.D., Ross J. "SYMPOSIUM: BEHAVIOR MODIFICATION BY DRUGSI. PHARMACOLOGY OF THE AMPHETAMINES." Pediatrics 49.5 (May 1972): 694-701.</ref> stimulants such as [[ephedrine]] or [[MDMA]] or after the individual insufflated an excessive amount of 2C-T-7- excessive being an amount greater than necessary to induce the full range of the drug's effects, such as the reported 35&nbsp;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.  Additionally, ephedrine, itself an MAO inhibitor, and MDMA may interact with any [[monoamine oxidase]] inhibition by 2C-T-7, which is presently speculative, to increase the cardiotoxicity of MDMA or ephedrine<ref>Breunig, Jan. "Mixing Medicines, Foods, Herbs, and Surgery: Monoamine Oxidase Inhibitors (MAOIs)." Plastic Surgical Nursing Pharmacology Review 23.2 (2003): 73-74.</ref>, which together were known to be present in two of the three deaths of 2C-T-7-intoxicated individuals.  Ephedrine's cardiovascular effects<ref>Dept. Pharmacologie, Universite De Geneve, Switzerlan, Kalix P. "The Pharmacology of Psychoactive Alkaloids from Ephedra and Catha." Journal of Ethnopharmacology 32.32 (1991): 201-8.</ref> have previously been shown to be potentiated by some MAO-A inhibitors<ref>Dingemanse, J., and T. Guentert. "Modification of the Cardiovascular Effects of Ephedrine by the Reversible Monoamine Oxidase A-Inhibitor Moclobemide." Journal of Cardiovascular Pharmacology 28.6 (Dec 1996): 856-61</ref>

==Legality==
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 since many countries have scheduled the chemical.

===Australia===
In Australia, [[2C-T-2]] and 2C-T-7 are covered by the country's comparatively strict [[analog (chemistry)|analogue]] drug laws.

===Canada===
2C-T-7 is unscheduled in Canada.

===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===
2C-T-2 became commercially available in Sweden in the summer of 1998, being sold in [[smartshop]]s similar to those in the Netherlands. On April 1, 1999, both 2C-T-2 and 2C-T-7, along with MBDB, BDB, [[2C-B]] and PMMA, were banned in Sweden. This was not done by appending these drugs to the country's normal drug laws, but by passing a new law, "Förordning (1999:58) om förbud mot vissa hälsofarliga varor," which banned the drugs as being materials dangerous to health.

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

===US===
On September 20, 2002, 2C-T-7 was classified as a [[Controlled Substances Act#Schedule I drugs|Schedule I]] substance in the United States by an emergency ruling by the [[Drug Enforcement Administration|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).<ref>{{cite web|url=http://www.dea.gov/programs/forensicsci/microgram/mg0104/mg0104.html|title=Micgrogram Bulletin Jan 2004|author=DEA}}</ref><ref>{{cite web|url=http://www.usdoj.gov/ndic/pubs11/12207/12207p.pdf|format=PDF|title=2C-T-7 Fast Facts|author=U.S. [[United States Department of Justice|Department of Justice]]}}</ref><ref>[http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm List of Schedule 1 drugs on the DEA Office of Diversion Control website]</ref>

==Notes==
{{Reflist|2}}

==See also==
* [[Aleph_(psychedelic)#Aleph-7|Aleph-7]]
* [[2C-B]]
* [[2C-T-21]]

== External links ==
* [http://erowid.org/chemicals/2ct7/ Erowid 2C-T-7 Vault]
* [http://www.erowid.org/library/books_online/pihkal/pihkal043.shtml PiHKAL #43 2C-T-7] by [[Alexander Shulgin]]
* [http://pihkal.info/read.php?domain=pk&id=43 2C-T-7 Entry in PiHKAL]

{{2C's}}
{{Hallucinogenic phenethylamines}}
{{Serotonergics}}
{{PiHKAL}}

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