N,alpha-Diethylphenylethylamine

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N,α-Diethylphenylethylamine
Ethylphenylbutanamine structure.png
Clinical data
Synonyms N,α-DEPEA
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C12H19N
Molar mass 177.285 g/mol
3D model (JSmol)

N,α-Diethylphenylethylamine (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 animals 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[edit]

In January 2013, the 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[edit]

References[edit]

  1. ^ Marzena Wójtowicz; Anna Jarek; Katarzyna Chajewska; Ewa Turek-Lepa; Dorota Kwiatkowska (November 2015). "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: 523–533. PMID 26311473. doi:10.1016/j.jpba.2015.07.025. 
  2. ^ Victor Uralets; Mike App; Sumandeep Rana; Stewart Morgan; Wayne Ross (January 2014). "Designer phenethylamines routinely found in human urine: 2-ethylamino-1-phenylbutane and 2-amino-1-phenylbutane.". Journal of Analytical Toxicology. 38 (2): 106–109. PMID 24451085. doi:10.1093/jat/bkt121. 
  3. ^ "2-Ethylamino-1-phenylbutane". Cayman Chemical. Retrieved 4 November 2015. 
  4. ^ a b Lee, Jaesin; Venhuis, Bastiaan J.; Heo, Sewoong; Choi, Hyeyoung; Seol, Ilung; Kim, Eunmi (2013). "Identification and quantitation of N,α-diethylphenethylamine in preworkout supplements sold via the Internet". Forensic Toxicology. 32: 148. doi:10.1007/s11419-013-0205-6. 
  5. ^ a b "Craze manufacturer disputes NSF's discovery of drug tainting". Nutraingredients. October 17, 2013. 
  6. ^ "Identification of N-ethyl-α-ethylphenethylamine in crystalline powder seized for suspected drug trafficking: A research chemical or a new designer drug?". Springer. January 2013. 
  7. ^ "Popular sports supplements contain meth-like compound". USA Today. October 25, 2013. 
  8. ^ Cohen, Pieter A.; Travis, John C.; Venhuis, Bastiaan J. (2014). "A methamphetamine analog (N,α-diethyl-phenylethylamine) identified in a mainstream dietary supplement". Drug Testing and Analysis. 6 (7–8): 805. PMID 24124092. doi:10.1002/dta.1578. 
  9. ^ Warning issued over CRAZE sports supplement. New Zealand Herald, 13 November 2013