2C-E

Last updated
2C-E
2C-E.svg
2C-E-3d-sticks.png
2C-E animation.gif
Names
Preferred IUPAC name
2-(4-Ethyl-2,5-dimethoxyphenyl)ethan-1-amine
Other names
4-Ethyl-2,5-dimethoxyphenethylamine, Aquarust
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.221.016 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3 Yes check.svgY
    Key: VDRGNAMREYBIHA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C12H19NO2/c1-4-9-7-12(15-3)10(5-6-13)8-11(9)14-2/h7-8H,4-6,13H2,1-3H3
    Key: VDRGNAMREYBIHA-UHFFFAOYAI
  • COc1cc(CC)c(cc1CCN)OC
Properties
C12H19NO2
Molar mass 209.289 g·mol−1
AppearanceWhite crystals
>70 mg/ml (20°C)
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin [1] 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. [2]

Contents

Properties

Mass Spectrometer Analysis: 2C-E MSpectro2C-E.gif
Mass Spectrometer Analysis: 2C-E

2,5-Dimethoxy-4-ethylphenethylamine is a colorless oil. Crystalline forms are obtained as the amine salt by reacting the free base with a mineral acid, typically hydrochloric acid (HCl).

Shulgin does not report an exact boiling point for the free base, stating only that during one synthesis the fraction boiling between 90 and 100 °C at 0.25 mmHg pressure was collected and converted to the hydrochloride salt. Shulgin reports the melting point of the hydrochloride salt as 208.5–210.5 °C. [3]

Effects

20 mg Capsules of 2C-E Ethylphenethylamine.jpg
20 mg Capsules of 2C-E
2C-E Pile 2,5-dimethoxy-4-ethyl.jpg
2C-E Pile

According to Shulgin, the duration of 2C-E's effects is generally between six and ten hours for an average dose, with the plateau lasting between three and six hours. [1]

2C-E's effects are often described as "neutral", in comparison with other psychedelic chemicals and even other 2C-x related molecules. In PiHKAL, Shulgin states:

"Here is another of the magical half-dozen. The range is purposefully broad. At 10 milligrams there have been some pretty rich +++ [nb 1] experiences, and yet I have had the report from one young lady of a 30 milligram trial that was very frightening. My first experience with 2C-E was really profound, and it is the substance of a chapter within the story. Several people have said, about 2C-E, "I don't think I like it, since it isn't that much fun. But I intend to explore it again." There is something here that will reward the experimenter. Someday, the full character of 2C-E will be understood, but for the moment, let it rest as being a difficult and worth-while material. A very much worth-while material."

Adverse effects

Adverse effects include tachycardia, hypertension, agitation, delirium, and hallucinations. [4] At least two deaths have been attributed to a 2C-E overdose. [4] [5] [6]

Drug prohibition laws

Australia

In Queensland, 2C-E was added to the 'Dangerous Drugs' list of the 'Drugs Misuse Act 1986' [7] by the 'Drugs Misuse Amendment Act 2008'. [8] Making it illegal to produce, supply or possess.

Canada

As of October 31, 2016, 2C-E is a controlled substance (Schedule III) in Canada. [9]

China

As of October 2015, 2C-E is a controlled substance in China. [10]

Denmark

2C-E is added to the list of Schedule B controlled substances. [11]

Finland

Scheduled in "government decree on psychoactive substances banned from the consumer market". [12]

Germany

2C-E is an Anlage I controlled drug.

New Zealand

New Zealand has a catch-all Analogues section in Schedule 3 / Class C of their drug laws that would make 2C-I, 2C-E, DOI, ephedrine, and pseudoephedrine Schedule 3 compounds in New Zealand.

Portugal

Portugal has decriminalized possession of all recreational drugs in quantities no more than a ten-day supply of that substance.[ citation needed ] However production and distribution (buying/selling) are a criminal offense.

Sweden

Sveriges riksdags health ministry ''Statens folkhälsoinstitut''  [ sv ] classified 2C-E as "health hazard" under the act ''Lagen om förbud mot vissa hälsofarliga varor''  [ sv ] (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Oct 1, 2004, in their regulation SFS 2004:696 listed as 2,5-dimetoxi-4-etylfenetylamin (2C-E), making it illegal to sell or possess. [13]

UK

In the United Kingdom, 2C-E is a Class A controlled substance. The UK has the strictest laws in the EU on designer drugs. The Misuse Of Drugs Act was amended in 2002 to include a "catch most" clause outlawing every drug, and possible future drug, from the LSD (ergoline) and MDMA (phenethylamine) chemical families (including 2C-E). The amendment is a near verbatim quote from the books of the American biochemist Alexander Shulgin, who obtained a PhD from the University of California, Berkeley. Dr. Shulgin, a former research chemist at the Dow Chemical Company, re-discovered the synthesis for MDMA in 1976 and published the syntheses for more than 200 phenethylamine compounds of his own invention, and 55 tryptamine compounds many of which were also his own invention. The Shulgins were motivated to release the synthesis information as a way to protect the public's access to information about psychedelic compounds, a goal Alexander Shulgin has noted many times.

United States

As of July 9, 2012, in the United States 2C-E is a Schedule I substance under the Food and Drug Administration Safety and Innovation Act of 2012, making possession, distribution and manufacture illegal. [14]

Notes

  1. ↑ Shulgin's +/- rating scale, per PiHKAL. See References below. Quoting: "Plus Three (+++) = Not only are the chronology and the nature of a drug's action quite clear, but ignoring its action is no longer an option. The subject is totally engaged in the experience, for better or worse."

Related Research Articles

<span class="mw-page-title-main">Alexander Shulgin</span> American chemist and recreational drug explorer (1925–2014)

Alexander Theodore "Sasha" Shulgin was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and pharmacology of such agents—in his mid-life and later, many through preparation in his home laboratory, and testing on himself. He is acknowledged to have introduced to broader use, in the late 1970s, the prior synthesized compound, MDMA ("ecstasy") in research psychopharmacology and in combination with conventional therapy, the latter through presentations and academic publications, including to psychologists; and for the rediscovery, occasional discovery, and regular synthesis and personal use and distribution, possibly of hundreds of psychoactive compounds. As such, Shulgin is seen both as a pioneering and a controversial participant in the emergence of the broad use of psychedelics.

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

PiHKAL: A Chemical Love Story is a book by 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-T-7</span> Psychedelic phenthylamine drug

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. 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. 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.

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

2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.

<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-D</span> Chemical compound

2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

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

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine 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">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">2C-O-4</span> Chemical compound

2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine) is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> Psychedelic drug

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

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

2C-F (4-fluoro-2,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 250 mg. 2C-F may be found as a brownish freebase oil, or as a white crystalline hydrochloride salt.

<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.

3,4-Methylenedioxy-<i>N</i>-hydroxy-<i>N</i>-methylamphetamine Chemical compound

3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH. MDHMA was first synthesized and assayed by Alexander Shulgin. In his book PiHKAL, Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 4–8 hours. He describes MDHMA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.

References

  1. 1 2 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. 2C-E in PiHKAL
  2. ↑ Papaseit, Esther; Olesti, Eulalia; Pérez-Mañá, Clara; Torrens, Marta; Grifell, Marc; Ventura, Mireia; Pozo, Oscar J.; de Sousa Fernandes Perna, Elizabeth B.; Ramaekers, Johannes G.; de la Torre, Rafael; Farré, Magí (2020). "Acute Effects of 2C-E in Humans: An Observational Study". Frontiers in Pharmacology. 11: 233. doi: 10.3389/fphar.2020.00233 . ISSN   1663-9812. PMC   7093582 . PMID   32256350.
  3. ↑ Shulgin, Alexander T.; Manning, Tania; Daley, Paul F. (2011). The Shulgin Index: Volume 1 (First ed.). Berkeley, CA: Transform Press. ISBN   978-0-9630096-3-0.
  4. 1 2 Topeff JM; Ellsworth H; Willhite LA; Bangh SA; Edwards EM; Cole JB (2011). "A case series of symptomatic patients, including one fatality, following 2C-E exposure". Clin. Toxicol. 49: 526.
  5. ↑ Pham, Sherisse (18 March 2011). "Man Arrested in Mass Drug Overdose That Killed 1 Teen and Left 10 People Hospitalized". ABC World News. Retrieved 29 June 2014.
  6. ↑ Sacks J; Ray MJ; Williams S; Opatowsky MJ (2012). "Fatal toxic leukoencephalopathy secondary to overdose of a new psychoactive designer drug 2C-E ("Europa")". Baylor University Medical Center Proceedings. 25 (4): 374–376. doi:10.1080/08998280.2012.11928883. PMC   3448584 . PMID   23077393.
  7. ↑ "In force legislation - Queensland Legislation - Queensland Government" (PDF). legislation.qld.gov.au. Archived (PDF) from the original on 2014-09-11.
  8. ↑ "Acts as passed - Queensland Legislation - Queensland Government" (PDF). legislation.qld.gov.au. Archived (PDF) from the original on 2015-04-07.
  9. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. Vol. 150, no. 9. 4 May 2016. Archived from the original on 2016-08-31.
  10. ↑ "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  11. ↑ Sundheds- og Ældreministeriet. "Bekendtgørelse om euforiserende stoffer - retsinformation.dk". retsinformation.dk. Archived from the original on 2013-10-04.
  12. ↑ https://finlex.fi/fi/laki/ajantasa/2014/20141130
  13. ↑ "20040696" (PDF). Archived (PDF) from the original on 2013-09-29. Retrieved 2013-09-06.
  14. ↑ "Erowid 2C-E Vault: Legal Status". erowid.org. Archived from the original on 2015-12-08.
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