2,5-dimethoxy-4-ethylphenylethylamine

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Structural formula
Structural formula of 2C-E
General
Surname 2,5-dimethoxy-4-ethylphenylethylamine
other names
  • 2- (4-ethyl-2,5-dimethoxyphenyl) ethanamine ( IUPAC )
  • 2C-E
  • Aquarust (scene name)
Molecular formula C 12 H 19 NO 2
Brief description

white crystals (hydrochloride)

External identifiers / databases
CAS number
  • 71539-34-9
  • 923013-67-6 (hydrochloride)
EC number 692-774-7
ECHA InfoCard 100.221.016
PubChem 24729233
ChemSpider 21106222
Wikidata Q209242
properties
Molar mass 209.29 g mol −1
Physical state

firmly

Melting point

210 ° C (hydrochloride)

solubility
  • ~ 30 mg / ml in EtOH
  • ~ 20 mg / ml in DMF
  • ~ 20 mg / ml in DMSO
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,5-Dimethoxy-4-ethylphenethylamine (also abbreviated to 2C-E ) is a psychedelic that structurally belongs to the group of phenylethylamines , as well as to the group of "2C" compounds . It is also known by the scene name Aquarust . It was first synthesized by Alexander Shulgin . 2C-E is mostly used in its hydrochloride form.

Pharmacological properties

Capsules filled with 20 mg 2C-E
200 mg of heaped 2C-E

Analytics

The reliable qualitative and quantitative detection of 2C-E succeeds after appropriate sample preparation by using HPLC and mass spectrometry .

Pharmacodynamics

It is believed that 2C-E, like most hallucinogens , binds to the 5-HT 2A receptors and thus creates the psychedelic effects. 2C-E acts (among other things) as a serotonin-noradrenaline reuptake inhibitor (IC 50 5-HT: 72 ± 16 μM NE: 89 ± 27 μM).

Users describe the effects of 2C-E as similar to those of other psychedelic phenylethylamines, but far more powerful. Compared to similar dimethoxyphenylethylamines like 2C-I and 2C-B, 2C-E is more likely to produce stronger synesthesia , sound distortion, expanded perception of music and visual appearances. Alexander Shulgin classifies 2C-E in his book PIHKAL (Phenethylamines I Have Known And Loved) as a member of the "magical half dozen".

Taking an SSRI usually reduces the intensity and length of the effects. The mixed consumption of serotonergic substances, which comprise a large part of intoxicants or psychotropic substances, in particular psychedelics , but also antidepressants such as SSRIs and MAOIs , however, generally harbors the risk of side effects of the dangerous and potentially fatal serotonin syndrome .

Pharmacokinetics

2C-E is taken orally or nasally. However, nasal consumption is described as very painful and uncomfortable. The effect sets in very quickly after nasal ingestion (1–10 min), while the oral onset is delayed (20–90 min). Shulgin gives the orally effective dose in the range of 10-25 mg, the duration of action with 8-12 hours.

Side effects

2C-E is a research chemical that has no therapeutic use as not enough is currently known about side effects, long-term harm, addictive potential, etc.

Legal status

Germany

With the passing of the 28th ordinance amending narcotics regulations on December 5, 2014, 2C-E was made subject to the Narcotics Act, trading and distribution have been prohibited since then ( Federal Law Gazette I, p. 1999 ).

In connection with a mass poisoning of twenty-nine conference participants, who may have experimented with the drug, in Handeloh in September 2015, a criminal law background is being examined, but primarily a civil law claim due to the induction of a large-scale deployment of rescue workers.

Austria

In Austria , 2C-E was not listed in the Suchtgiftverordnung SV and was therefore legal. Since February 1, 2012, however, 2C-E has been subject to the "Federal Act on Protection against Health Risks in Connection with New Psychoactive Substances" (New Psychoactive Substances Act, NPSG). Similar to the Addictive Substances Act, the handling of “new psychoactive substances” (“Legal Highs” or Research Chemicals) is prohibited by law. More precisely, the production, import and export as well as the transfer and procurement (transfer) of such substances in order to benefit from them are prohibited if this is done for the purpose of human consumption.

Switzerland

In Switzerland , 2C-E will be subject to the Narcotics Act with the entry into force of the revised Narcotics Ordinance by Swissmedic on December 1, 2011, and will therefore be illegal from this point on. Importation, possession, distribution etc. are punished according to the Narcotics Act.

United States

In the USA , 2C-E has been on Schedule I since July 9, 2012. Possession, trade and production are therefore punishable.

literature

  • Alexander Shulgin, Ann Shulgin: PIHKAL - A Chemical Love Story. Transform Press, ISBN 0-9630096-0-5 .
  • Nadja Wirth: Ecstasy - Mushrooms, Speed ​​& Co. The info book. Econ Paperback, ISBN 3-548-75061-3 .
  • Daniel Trachsel, Nicolas Richard: Psychedelic Chemistry - 2,5-Dimethoxy-4-ethylphenylethylamine. Nachtschatten Verlag, 2000, ISBN 3-907080-53-X , p. 69 ff.
  • DS Theobald, HH Maurer: Studies on the metabolism and toxicological detection of the designer drug 4-ethyl-2,5-dimethoxy-beta-phenethylamine (2C-E) in rat urine using gas chromatographic-mass spectrometric techniques. In: Journal of chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. Volume 842, number 2, October 2006, pp. 76-90, doi : 10.1016 / j.jchromb.2006.03.001 . PMID 16600701 .

Web links

Individual evidence

  1. ↑ a b c d PiHKAL # 24 2C-E
  2. ↑ SWGDRUG Monographs: 2C-E Monograph (PDF; 298 kB), accessed on May 20, 2013.
  3. ↑ a b c Cayman Chemical Company: 2C-E MSDS (PDF; 23 kB), accessed on May 20, 2013
  4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  5. ↑ Urban Dictionary: Aquarust , accessed September 30, 2015.
  6. ↑ Van Vrancken MJ, Benavides R, Wians FH Jr: Identification of designer drug 2C-E (4-ethyl-2, 5-dimethoxy-phenethylamine) in urine following a drug overdose. Proc (Bayl Univ Med Cent). 2013 Jan; 26 (1): 58-61. PMID 23382618 .
  7. ↑ CA Villalobos, P. Bull, P. Sáez, BK Cassels, JP Huidobro-Toro: 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT 2A receptor antagonists in Xenopus laevis oocytes , in: Br. J. Pharmacol. , 2004 , 141  (7), pp. 1167-1174; PMC 1574890 (free full text).
  8. ↑ Pablo R. Moya, Kelly A. Berg, Manuel A. Gutiérrez-Hernandez, Patricio Sáez-Briones, Miguel Reyes-Parada, Bruce K. Cassels, William P. Clarke: "Functional Selectivity of Hallucinogenic Phenethylamine and Phenylisopropylamine Derivatives in Human 5 - Hydroxytryptamine (5-HT) 2A and 5-HT 2C Receptors ", in: Journal of Pharmacology and Experimental Therapeutics , 2007, 321 (3), pp. 1054-1061; doi : 10.1124 / jpet.106.117507 .
  9. ↑ F. Nagai, R. Nonaka, K. Satoh Hisashi Kamimura: The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. In: European journal of pharmacology. Volume 559, Number 2-3, March 2007, pp. 132-137, doi : 10.1016 / j.ejphar.2006.11.075 . PMID 17223101 .
  10. ↑ 2C-E . In: Erowid . (English)
  11. ↑ Drug Intoxication in Handeloh: Intentional or Accidental? ( Memento from September 7, 2015 in the Internet Archive )
  12. ↑ SZ.de of September 5, 2015: Staggering naturopaths trigger large-scale deployment ; NDR.de from September 5, 2015: Criminal proceedings after mass drug poisoning ; Spiegel Online from September 25, 2015: Heilpraktikertreffen: Mass intoxication was probably a therapy trip .
  13. ^ Austrian Chamber of Pharmacists: Narcotics Ordinance
  14. ↑ Parliament Republic of Austria: New Psychoactive Substances Act - NPSG (1518 dB) (XXIV.GP)
  15. ↑ Federal Department of the Interior (FDHA): Ordinance of the FDHA on the registers of narcotics, psychotropic substances, precursor substances and auxiliary chemicals of November 21, 2011.
  16. ↑ Erowid.org, Legal Status of 2C-E