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2c T 7 Synthesis Essay

The skeletal formula of 2C-T-7.
2C-T-7, Beautiful, Blue Mystic, 7th Heaven
2,5-Dimethoxy-4-(propylthio)phenethylamine
2-[2,5-Dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine
Psychedelic
Phenethylamine

2,5-Dimethoxy-4-propylthiophenethylamine (also known as 2C-T-7, Blue Mystic,[4] and Beautiful,[4] among others) is a psychedelic substance of the phenethylamine chemical class that produces psychedelic and entactogenic effects when administered.

2C-T-7 was first synthesized by Alexander Shulgin and documented in his book PiHKAL ("Phenethylamines I Have Known and Loved").[5] It is a member of the 2C-x family of psychedelic phenethylamines, all of which were derived from the systematic modification of the mescaline molecule.

In contrast to other members of the 2C-x family, 2C-T-7 has gained a reputation of being an unpredictable, dose-sensitive psychedelic capable of producing strong visual effects and an intense body load, which can manifest as a dangerous delirium in extreme cases. Many reports indicate that the physical effects are too severe for inexperienced users or those with pre-existing medical conditions.

This particular compound is part of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds, all of which -- with the exception of mescaline -- he designed, synthesized and tested on himself. They can be found within the first book of PiHKAL, and are as follows: Mescaline, DOM, 2C-B, 2C-E, 2C-T-2 and 2C-T-7.[6]

Chemistry

2C-T-7, or 2,5-dimethoxy-4-propylthiophenethylamine, is a substituted phenethylamine featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain.

2C-T-7 belongs to the 2C family of phenethylamines, which contain methoxy functional groups CH3O- attached to carbons R2 and R5 of the benzene ring. 2C-T-7 is also substituted at R4 with a propyl thioether group.

2C-T-7 is analogous to 2C-T-2; the two differ by the length of the alkane chain in their thioether functional group.[7]

Pharmacology

Further information: Serotonergic psychedelic

2C-T-7's psychedelic effects have been shown to come from its efficacy at the 5-HT2A receptor as a partial agonist.[8] However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

As the 2,5-desmethoxy derivative of 2C-T-7 has been shown to be a moderate monoamine oxidase A inhibitor, this substance is widely thought to have MAOI effects.

Subjective effects

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWikicontributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Experience reports

There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:

Toxicity and harm potential

This toxicity and harm potential section is a stub.

As such, it may contain incomplete or even dangerously wrong information. You can help by expanding upon or correcting it.
We also recommend that you practice diligent independent research and the most thorough harm reduction practices when using this substance.

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

As of August 2007, there have been at least three reported deaths associated with the use of 2C-T-7. These incidents occurred with insufflated doses of 30 mg or more[9], or in combination with stimulants such as MDMA,[citation needed]. There have also been a number of reports describing concerning physical side effects and hospitalizations, typically following insufflation.[10]

It is strongly discouraged to administer 2C-T-7 non-orally because this can cause vomiting, numerous negative side effects, or death at high doses. In Erowid's Fall 2000 2C-T-7 survey, it was reported that the insufflation of 2C-T-7 resulted in more negative side effects than oral administration.[citation needed]

It is strongly recommended that one use harm reduction practices, such as volumetric dosing, when using this substance to ensure the accurate administration of the intended dose.

Tolerance and addiction potential

2C-T-7 is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.

Tolerance to the effects of 2C-T-7 are built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). 2C-T-7 presents cross-tolerance with all psychedelics, meaning that after the consumption of 2C-T-7 all psychedelics will have a reduced effect.

Dangerous interactions

Although many psychoactive substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

If 2C-T-7 does have MAOI effects as commonly speculated, this could indicate that 2C-T-7 is more likely to induce serotonin syndrome or general neurotransmitter overload (especially at high dosages) than other serotonergic psychedelics.[11] This may make it dangerous to combine it with other MAOIs, stimulants and certain substances which releases neurotransmitters such as serotonin or dopamine. These substances include but are not limited to:

Legality

  • Australia - In Australia, 2C-T-2 and 2C-T-7 are covered by the country's analog drug laws.[citation needed]
  • Austria: 2C-T-7 is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)
  • Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[12]
  • Canada: 2C-T-7 is considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.[13]
  • China - As of October 2015 2C-T-7 is a controlled substance in China.[14]
  • Germany - Possession, production and sale is illegal.[15]
  • Latvia - 2C-T-7 is a Schedule I controlled substance in Latvia.[16]
  • Netherlands - The Netherlands was the first country in the world to ban 2C-T-7 after being sold in smart shops 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.[citation needed]
  • Sweden - The drug is Schedule I in Sweden.[17] 2C-T-7 was first classified as a health hazard under the act "Lagen om förbud mot vissa hälsofarliga varor" (translated as "the Act on the Prohibition of Certain Goods Dangerous to Health") that made it illegal to sell or possess as of April 1, 1999.[citation needed]
  • Switzerland: Possession, production and sale is illegal.[18]
  • United Kingdom - 2C-T-7 is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.[19]
  • 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 which permanently placed 2C-T-7 in Schedule I.[citation needed]

See also

External links

References

  1. ↑Third Confirmed 2C-T-7 Death by Erowid Apr 10, 2001 | https://www.erowid.org/chemicals/2ct7/2ct7_death3.shtml
  2. ↑A Reported 2C-T-7 Death by Erowid July 2003 | https://www.erowid.org/chemicals/2ct7/2ct7_death1.shtml
  3. ↑Second Reported 2C-T-7 Death by Erowid Apr 2, 2001 | https://www.erowid.org/chemicals/2ct7/2ct7_death2.shtml
  4. 4.04.1Zimmerman, M.M., “The identification of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7).” Microgram, Vol. XXXIV, No. 7, July 2001, pp. 169-173.
  5. ↑https://erowid.org/library/books_online/pihkal/pihkal.shtml | PiHKAL
  6. ↑https://erowid.org/library/books_online/pihkal/pihkal.shtml | PiHKAL
  7. ↑http://isomerdesign.com/PiHKAL/read.php?id=43
  8. ↑Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats | http://link.springer.com/article/10.1007%2Fs00213-005-0009-4
  9. ↑Curtis, B., Kemp, P., Harty, L., Choi, C., & Christensen, D. (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.
  10. ↑2C-T-7 Overdoses & Delirium | https://www.erowid.org/chemicals/2ct7/2ct7_effects.shtml#overdose
  11. ↑Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling | http://pubs.acs.org/doi/abs/10.1021/jm0493109
  12. ↑http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
  13. ↑Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28
  14. "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. 27 September 2015. Retrieved 1 October 2015. 
  15. ↑BtMG Anlage I | https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html
  16. ↑Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086
  17. ↑http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf
  18. ↑http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html
  19. ↑United Kingdom. (1977). Misuse of Drugs Act 1971 (S.I. 1977/1243). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/1977/1243/made
    • Stimulation - In terms of its effects on the physical energy levels of the user, 2C-T-7 is generally considered to be energetic and stimulating in a fashion is comparable to that of other phenethylamines such as 2C-B, 2C-E and 2C-P. However, at certain doses and contexts, it may produce periods of notable sedation.
    • Spontaneous physical sensations - The "body high" of 2C-T-7 is intense, but in comparison to 2C-E or 2C-B, it can be considered mild though is still capable of becoming very powerful and highly physically euphoric. It is similar yet distinct from the "body high" experienced on 2C-E, 2C-B, and LSD. The sensation itself can be described as intense and will manifest itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves.
    • Bodily control enhancement - Although this component is capable of manifesting itself in a distinct and noticeable fashion, for most users it does not generally seem to be as apparent or intense as the same component found within LSD and 2C-B.
    • Changes in felt bodily form
    • Tactile enhancement
    • Temperature regulation suppression
    • Abnormal heartbeat[citation needed]
    • Increased blood pressure[citation needed]
    • Increased heart rate[citation needed]
    • Dehydration
    • Diarrhea
    • Difficulty urinating or Frequent urination
    • Dizziness
    • Headaches
    • Increased perspiration
    • Muscle contractions
    • Muscle spasms
    • Muscle cramps
    • Nausea - Mild to extreme nausea is commonly reported when consumed in moderate to high dosages, and either passes once the user has vomited or gradually fades by itself as the peak sets in.
    • Stomach bloating
    • Stomach cramps
    • Teeth grinding
    • Excessive yawning
    • Pupil dilation
    • Watery eyes
  • Enhancements

    Distortions

    Geometry

    The visual geometry that is present throughout this trip can be described as more similar in appearance to that of 4-AcO-DMT or ayahuasca than that of LSD, 2C-B or 2C-I. They can be comprehensively described as structured in their organization, organic in geometric style, intricate in complexity, large, fast and smooth in motion, colorful in scheme, glossy in color, sharp in their edges and equally rounded and angular in their corners. It gives off a contradictory natural and synthetic feel with slightly more mystical and shamanic undertones in comparison to other phenethylamines. At higher dosages, they are equally likely to result in states of Level 8A visual geometry or Level 8B. There seems to be a visual geometry that is extremely similar to 2C-E and 2C-P and can be described as equal in intensity or complexity and equal in proportion to the accompanying cognitive and physical effects.

    Hallucinatory states

    2C-T-7 produces a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. This holds particularly true in comparison to other substances within the phenethylamine family. These effects include:

    • Transformations
    • Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - This effect is very consistent in dark environments at appropriately high dosages. They can be comprehensively described through their variations as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.

Sulfurous Samadhi:
Table of Contents
Intro
Chemistry
History
Stolaroff Survey
Hardison's Survey
User Survey
Pharmacology
Legal
Conclusion

Appendices:
User Quotes:
2C-T-2
2C-T-7
Comparisons

Synthesis:
  • 2C-T-2
  • 2C-T-7

    Product Lit:
  • 2C-T-2
  • Blue Mystic 1
  • Blue Mystic 2
  • Retailer Note
  • Bibliography


  • Sulfurous Samadhi
    2C-T-7 Synthesis
    by Murple, Feb 6, 2001



    2C-T-7 Synthesis



    Taken from PIHKAL by Alexander Shulgin

    To a solution of 3.4 g of KOH pellets in 50 mL hot MeOH, there was added a mixture of 6.8 g 2,5-dimethoxythiophenol (see under the recipe for 2C-T-2 for its preparation) and 7.4 g (n)-propylbromide dissolved in 20 mL MeOH. The reaction was exothermic, with the deposition of white solids. This was heated on the steam bath for 0.5 h, added to 800 mL H2O, additional aqueous NaOH added until the pH was basic, and extracted with 3x75 mL CH2Cl2. The pooled extracts were washed with dilute NaOH, and the solvent removed under vacuum. The residue was 2,5-dimethoxyphenyl (n)-propyl sulfide which was obtained as a pale yellow oil, and which weighed 8.9 g. It had a light pleasant fruity smell, and was sufficiently pure for use in the next reaction without distillation.

    A mixture of 14.4 g POCl3 and 13.4 g N-methylformanilide was heated for 10 min on the steam bath. To this claret-colored solution was added 8.9 g of 2,5-dimethoxyphenyl (n)-propyl sulfide, and the mixture heated an additional 25 min on the steam bath. This was then added to 800 mL of well-stirred warm H2O (pre-heated to 55 �C) and the stirring continued until the oily phase had completely solidified (about 15 minutes). The resulting brown sugar-like solids were removed by filtration, and washed with additional H2O. After sucking as dry as possible, they were dissolved in an equal weight of boiling MeOH which, after cooling in an ice-bath, deposited pale ivory colored crystals. After filtration, modest washing with cold MeOH, and air drying to constant weight, there was obtained 8.3 g of 2,5-dimethoxy-4-(n-propyl-thio)benzaldehyde with a mp of 73-76 �C. Recrystallization from 2.5 volumes of MeOH provided a white analytical sample with mp 76-77 �C. The NMR spectrum in CDCl3 was textbook perfect, with the two aromatic protons showing singlet signals at 6.81 and 7.27 ppm, giving assurance that the assigned location of the introduced aldehyde group was correct.

    To a solution of 4.0 g 2,5-dimethoxy-(n-propylthio)benzaldehyde in 20 g of nitromethane there was added 0.23 g of anhydrous ammonium acetate, and the mixture was heated on the steam bath for 1 h. The clear orange solution was decanted from some insoluble material and the excess nitromethane removed under vacuum. The orange-yellow crystalline material that remained was crystallized from 70 mL boiling IPA which, on slow cooling, deposited 2,5-dimethoxy-beta-nitro-4-(n)-propylthiostyrene as orange crystals. After their removal by filtration and air-drying to constant weight, they weighed 3.6 g, and had a mp of 120-121 �C. Anal. (C13H17NO4S) C,H.

    A solution of LAH (132 mL of a 1 M solution in THF) was cooled, under He, to 0 �C with an external ice bath. With good stirring there was added 3.5 mL 100% H2SO4 dropwise, to minimize charring. This was followed by the addition of 8.4 g 2,5-dimethoxy-beta-nitro-4-(n)-propylthiostyrene in 50 mL anhydrous THF. There was an immediate loss of color. After a few min further stirring, the tem-perature was brought up to a gentle reflux on the steam bath, then all was cooled again to 0 �C. The excess hydride was destroyed by the cautious addition of IPA (21 mL required) followed by sufficent 5% NaOH to give a white granular character to the oxides, and to assure that the reaction mixture was basic (15 mL was used). The reaction mixture was filtered and the filter cake washed first with THF and then with IPA. The filtrate and washes were combined and stripped of solvent under vacuum providing about 6 g of a pale amber oil. Without any further purification, this was distilled at 140-150 �C at 0.25 mm/Hg to give 4.8 g of product as a clear white oil. This was dissolved in 25 mL IPA, and neutralized with concentrated HCl forming immediate crystals of the hydrochloride salt in the alcohol solvent. An equal volume of anhydrous Et2O was added, and after complete grinding and mixing, 2,5-dimethoxy-4-(n)-propylthiophenethylamine hydrochloride (2C-T-7) was removed by filtration, Et2O washed, and air dried to constant weight. The resulting spectacular white crystals weighed 5.2 g.

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