PCPr

PCPr is an arylcyclohexylamine dissociative anesthetic drug with hallucinogenic and stimulant effects. It is around the same potency as phencyclidine, although slightly less potent than its ethyl homologue eticyclidine,[1] and has reportedly been sold as a designer drug in Germany and other European countries since the late 1990s.[2][3]

PCPr
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • 1-phenyl-N-propylcyclohexanamine
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H23N
Molar mass217.356 g·mol−1
3D model (JSmol)
SMILES
  • N(CCC)C2(c1ccccc1)CCCCC2
InChI
  • InChI=1S/C15H23N/c1-2-13-16-15(11-7-4-8-12-15)14-9-5-3-6-10-14/h3,5-6,9-10,16H,2,4,7-8,11-13H2,1H3 Y
  • Key:KHXNTQRMMGXPQW-UHFFFAOYSA-N Y
  (verify)

Several other related derivatives have also been encountered, with the n-propyl group of PCPr replaced by a 2-methoxyethyl, 2-ethoxyethyl or 3-methoxypropyl group to form PCMEA, PCEEA and PCMPA respectively.[4][5][6]

PCMEA, PCEEA and PCMPA

References
  1. MADDOX VH, GODEFROI EF, PARCELL RF (March 1965). "The Synthesis of Phencyclidine and Other 1-Arylcyclohexylamines". Journal of Medicinal Chemistry. 8 (2): 230–5. doi:10.1021/jm00326a019. PMID 14332667.
  2. Sauer C, Peters FT, Staack RF, Fritschi G, Maurer HH (April 2008). "Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry". Journal of Chromatography A. 1186 (1–2): 380–90. doi:10.1016/j.chroma.2007.11.002. PMID 18035363.
  3. Christoph Sauer. Phencyclidine Derivatives – A new Class of Designer Drugs. Studies on the Metabolism and Toxicological Analysis. Universität des Saarlandes, 2008
  4. Sauer C, Peters FT, Staack RF, Fritschi G, Maurer HH (March 2008). "New designer drugs N-(1-phenylcyclohexyl)-2-ethoxyethanamine (PCEEA) and N-(1-phenylcyclohexyl)-2-methoxyethanamine (PCMEA): Studies on their metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric techniques". Journal of Mass Spectrometry. 43 (3): 305–16. Bibcode:2008JMSp...43..305S. doi:10.1002/jms.1312. PMID 17968862.
  5. Sauer C, Peters FT, Schwaninger AE, Meyer MR, Maurer HH (February 2009). "Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N-(1-phenyl cyclohexyl)-2-ethoxyethanamine and N-(1-phenylcyclohexyl)-2-methoxyethanamine". Biochemical Pharmacology. 77 (3): 444–50. doi:10.1016/j.bcp.2008.10.024. PMID 19022226.
  6. Sauer C, Peters FT, Staack RF, Fritschi G, Maurer HH (October 2008). "Metabolism and toxicological detection of the designer drug N-(1-phenylcyclohexyl)-3-methoxypropanamine (PCMPA) in rat urine using gas chromatography-mass spectrometry". Forensic Science International. 181 (1–3): 47–51. doi:10.1016/j.forsciint.2008.09.001. PMID 18922655.


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