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 ;
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 ; Key:KHXNTQRMMGXPQW-UHFFFAOYSA-N ;
	(verify)

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]

References

^ 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.
^ 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.
^ Christoph Sauer. Phencyclidine Derivatives – A new Class of Designer Drugs. Studies on the Metabolism and Toxicological Analysis. Universität des Saarlandes, 2008
^ 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.
^ 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.
^ 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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[pmid14332667-1] 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.

[pmid18035363-2] 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

[pmid17968862-4] 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.

[pmid19022226-5] 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.

[pmid18922655-6] 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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[2]

[3]

[4]

[5]

[6]

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
(verify)