Chemistry:N,α-Diethylphenethylamine

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Short description: Chemical compound


N,α-Diethylphenethylamine
N,α-Diethylphenylethylamine.svg
Clinical data
Other namesN,α-Diethylphenylethylamine
N,α-Diethylbenzeneethanamine
2-Amino-N-ethyl-1-phenylbutane
2-Ethylamino-1-phenylbutane
Ethyl(1-phenylbutan-2-yl)amine
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC12H19N
Molar mass177.291 g·mol−1
3D model (JSmol)

N,α-Diethylphenethylamine (N,α-DEPEA, 2-ethylamino-1-phenylbutane, EAPB) is a close chemical analog of methamphetamine, which has been sold as a designer drug.[1][2][3] It was originally patented by Knoll Pharma as one of several analogs for pharmaceutical applications. In animal models these analogs showed properties of cognitive enhancement and increased pain tolerance.[4] Nevertheless, this class of compounds was never developed into a medicine. N,α-DEPEA has not been studied in humans, but experts such as Pieter Cohen of Harvard Medical School expect it to be less potent than methamphetamine, but greater than ephedrine.[5]

Adulterant in nutritional supplements

In January 2013, the South Korean authorities reported seizing a large quantity of the pure material, predicting it would soon be found on the market.[6] Later in 2013, it was found as an adulterant in biologically significant amounts in the pre-workout supplements Craze (marketed by Driven Sports, Inc.) and Detonate (marketed by Gaspari Nutrition).[4][7] It was falsely claimed to be Dendrobium extract.[5][8][9]

See also

References

  1. "Determination of designer doping agent--2-ethylamino-1-phenylbutane--in dietary supplements and excretion study following single oral supplement dose". Journal of Pharmaceutical and Biomedical Analysis 115: 523–33. November 2015. doi:10.1016/j.jpba.2015.07.025. PMID 26311473. 
  2. "Designer phenethylamines routinely found in human urine: 2-ethylamino-1-phenylbutane and 2-amino-1-phenylbutane". Journal of Analytical Toxicology 38 (2): 106–9. March 2014. doi:10.1093/jat/bkt121. PMID 24451085. 
  3. "2-Ethylamino-1-phenylbutane". Cayman Chemical. https://www.caymanchem.com/app/template/Product.vm/catalog/9001863. 
  4. 4.0 4.1 "Identification and quantitation of N,α-diethylphenethylamine in preworkout supplements sold via the Internet". Forensic Toxicology 32: 148–153. 2013. doi:10.1007/s11419-013-0205-6. 
  5. 5.0 5.1 "Craze manufacturer disputes NSF's discovery of drug tainting". Nutraingredients. October 17, 2013. http://www.nutraingredients-usa.com/Regulation/Craze-manufacturer-disputes-NSF-s-discovery-of-drug-tainting. 
  6. "Identification of N-ethyl-α-ethylphenethylamine in crystalline powder seized for suspected drug trafficking: A research chemical or a new designer drug?". Forensic Toxicology 31: 54–58. January 2013. doi:10.1007/s11419-012-0158-1. 
  7. "Popular sports supplements contain meth-like compound". USA Today. October 25, 2013. https://www.usatoday.com/story/news/nation/2013/10/14/tests-of-supplements-craze-and-detonate-find-methamphetamine-like-compound/2968041/. 
  8. "A methamphetamine analog (N,α-diethyl-phenylethylamine) identified in a mainstream dietary supplement". Drug Testing and Analysis 6 (7–8): 805–7. 2014. doi:10.1002/dta.1578. PMID 24124092. 
  9. Warning issued over CRAZE sports supplement. New Zealand Herald, 13 November 2013