2C-T-7

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2C-T-7
2C-T-7 2DACS.svg
2C-T-7-3d-sticks.png
2C-T-7 powder.jpg
Names
Preferred IUPAC name
2-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine
Other names
2,5-Dimethoxy-4-(propylsulfanyl)phenethylamine, 2,5-Dimethoxy-4-(propylthio)phenethylamine, Blue Mystic, Tweety-Bird Mescaline
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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
  • 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
    Key: OLEVEPDJOFPJTF-UHFFFAOYAR
  • COc1cc(SCCC)c(cc1CCN)OC
Properties
C13H21NO2S
Molar mass 255.38 g/mol
Melting point 206 to 207 °C (403 to 405 °F; 479 to 480 K)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2C-T-7 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. [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. It is known on the streets as Blue Mystic or 7th Heaven. [2] [3] 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 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. [4] 2C-T-7 has structural and pharmacodynamic properties similar to those of 2C-T-2.

Effects

2C-T-7 is psychedelic. [5] [6] In PiHKAL, Shulgin records that the hallucinations are unique, and that the chemical may cause muscle tension and an altered vocal quality. [7] Shulgin rated it as one of the "magical half-dozen" most important psychedelic phenethylamine compounds, together with Mescaline, 2C-B and 2C-T-2. [8]

Deaths

The Partnership for a Drug-Free America reports that 2C-T-7 can be lethal even in small doses; [9] however, they provide no source for their claim and of the three known deaths of 2C-T-7 intoxicated individuals, all involved either excessive 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 mg or more [10] [11] 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." "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.</ref> as well as a number of very uncomfortably intense effects and hospitalizations, these mostly followed insufflation of 2C-T-7. In January 2002, Rolling Stone published an article about 2C-T-7 entitled "The New (legal) Killer Drug", [12] although the legal status of the drug was misrepresented in the article, as 2C-T-7 may have been already illegal under the United States' legally ambiguous analog act. [13] A detailed response on the website Disinformation challenged the accuracy of much of the reporting in that Rolling Stone article. [14]

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 [15] 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 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.

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.

Germany

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

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. [16]

China

As of October 2015 2C-T-7 is a controlled substance in China. [17]

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. [18] 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 [19] 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). [20] [21] [22]

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."

<span class="mw-page-title-main">2C-B</span> Psychoactive drug

2C-B (4-bromo-2,5-dimethoxyphenethylamine) is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. The substance was first synthesized by Alexander Shulgin in 1974, and gained an initial reputation for potential psychotherapeutic use, but its use has been limited to mainly recreational use. To date, there is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant, and hallucinogen, and less commonly as an entactogen, and empathogen.

<span class="mw-page-title-main">2C-E</span> Chemical compound

2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and documented in his book PiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.

<span class="mw-page-title-main">2C-C</span> Chemical compound

2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated. 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.

<span class="mw-page-title-main">2C-T-21</span> Psychedelic phenethylamine drug

2C-T-21 is a psychedelic phenethylamine of the 2C family sometimes used as an entheogen. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2,5-Dimethoxy-4-bromoamphetamine</span> Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

<span class="mw-page-title-main">2C-T-8</span> Chemical compound

2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.

<span class="mw-page-title-main">2C-N</span> Chemical compound

2C-N (2,5-dimethoxy-4-nitrophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2C-T-4</span> Chemical compound

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

<span class="mw-page-title-main">2C-P</span> Chemical compound

2C-P is a relatively potent and long acting psychedelic phenethylamine of the 2C family.

<span class="mw-page-title-main">2C-G</span> Chemical compound

2C-G is a psychedelic phenethylamine of the 2C-series. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL, 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.

<span class="mw-page-title-main">2,5-Dimethoxy-4-chloroamphetamine</span> Chemical compound

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was presumably first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

<span class="mw-page-title-main">2C-T</span> Chemical compound

2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.

<span class="mw-page-title-main">2,5-Dimethoxy-4-nitroamphetamine</span> Chemical compound

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug and amphetamine. It is an analog of DOM and DOB. It is also closely related to 2C-N.

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

<span class="mw-page-title-main">2C-T-13</span> Chemical compound

2C-T-13 is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL.

<span class="mw-page-title-main">2C-T-15</span> Chemical compound

2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">2C-T-17</span> Chemical compound

2C-T-17 or 2,5-dimethoxy-4-(β-secbutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

<span class="mw-page-title-main">2C-H</span> Chemical compound

2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.

<span class="mw-page-title-main">2,5-Dimethoxy-4-fluoroamphetamine</span> Chemical compound

2,5-Dimethoxy-4-fluoroamphetamine (DOF) is a psychedelic drug of the phenethylamine and amphetamine classes. Alexander Shulgin briefly describes DOF in his book PiHKAL:

Animal studies that have compared DOF to the highly potent DOI and DOB imply that the human activity will be some four to six times less than these two heavier halide analogues.

References

  1. ↑ Shulgin A. "PIHKAL #43".
  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
  3. ↑ O'Connell C (August 19, 2002). "A psychedelic summer". Newsweek.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ "Erowid 2C-T-7 Vault: Sulfurous Samadhi: Stolaroff's & Well's Study". erowid.org. February 6, 2001. Retrieved October 30, 2023.
  7. ↑ Shulgin A (June 28, 2001). "2C-T-7". Ask Dr Shulgin. Centre for Cognitive Liberty and Ethics (COLE). Retrieved August 28, 2009.
  8. ↑ Shulgin A (1990). ""PIHKAL" - The Chemical Story". www.erowid.org. Retrieved October 30, 2023.
  9. ↑ Partnership for a Drug-Free America. "2C-B, 2C-T-7". Archived from the original on October 19, 2006. Retrieved October 4, 2006.
  10. ↑ 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): 493–8. 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.
  11. ↑ 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
  12. ↑ "The New (Legal) Killer Drug". Rolling Stone , January 10, 2002, issue 888: 44–49.
  13. ↑ 21 USC §813
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ Gazette Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada (May 4, 2016). "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". gazette.gc.ca.
  17. ↑ "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.
  18. ↑ "Läkemedelsverkets författningssamling" (PDF).
  19. ↑ "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.
  20. ↑ DEA. "Micgrogram Bulletin Jan 2004". Archived from the original on February 12, 2007. Retrieved December 19, 2006.
  21. ↑ U.S. Department of Justice. "2C-T-7 Fast Facts" (PDF).
  22. ↑ "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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