PCPr

PCPr

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule III DE: Anlage I (Authorized scientific use only) UK: Class B
Identifiers
IUPAC name 1-phenyl-N-propylcyclohexanamine
CAS Number	18949-81-0
ChemSpider	521518  Y
UNII	6H9B5S0I6S
CompTox Dashboard (EPA)	DTXSID20172359
Chemical and physical data
Formula	C15H23N
Molar mass	217.356 g·mol−1
3D model (JSmol)	Interactive image
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
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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 the 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]}

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.