NPDPA

NPDPA
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; Illegal in Sweden;
Identifiers
	IUPAC name N-(propan-2-yl)-1,2-diphenylethylamine;
CAS Number	774118-46-6 ;
PubChem CID	110817;
ChemSpider	99466;
UNII	7DZ8JAX6K7;
CompTox Dashboard (EPA)	DTXSID601336208 ;
Chemical and physical data
Formula	C17H21N
Molar mass	239.362 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccccc1CC(NC(C)C)c2ccccc2;
	InChI InChI=1S/C17H21N/c1-14(2)18-17(16-11-7-4-8-12-16)13-15-9-5-3-6-10-15/h3-12,14,17-18H,13H2,1-2H3; Key:FBRJTEBLJRHAQX-UHFFFAOYSA-N;

NPDPA (also known as isopropylphenidine or isophenidine) is a dissociative anesthetic that has been sold online as a designer drug.^[1]^[2]^[3]^[4] It was first identified in Germany in 2008, and while it has never been as widely sold as related compounds such as diphenidine and ephenidine, it has continued to show up in seized drug samples occasionally,^[5] and was banned in Sweden in 2015.

Metabolism

Isopropylphenidine's metabolic pathway consists of N-oxidation, N-dealkylation, mono- and bis-hydroxylation of the benzene ring, and hydroxylation of the phenyl ring only after N-dealkylation. The dihydroxy metabolites were conjugated by methylation of one hydroxy group, and hydroxy metabolites by glucuronidation or sulfation.^[3]^[6]

Legality

Sweden's public health agency suggested that NPDPA be classified as a hazardous substance on 1 June 2015. Due to that suggestion it became a scheduled substance in Sweden, as of 18 August 2015.^[7] It has also been proposed for control in Germany under analogue provisions, though these have not yet come into force as of 2016.

References

^ Morris H, Wallach J (July–August 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID 24678061.
^ Meyer MR, Orschiedt T, Maurer HH (February 2013). "Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein". Toxicology Letters. 217 (2): 137–42. doi:10.1016/j.toxlet.2012.12.012. PMID 23273999.
^ ^a ^b Wink CS, Meyer GM, Wissenbach DK, Jacobsen-Bauer A, Meyer MR, Maurer HH (October 2014). "Lefetamine-derived designer drugs N-ethyl-1,2-diphenylethylamine (NEDPA) and N-iso-propyl-1,2-diphenylethylamine (NPDPA): metabolism and detectability in rat urine using GC-MS, LC-MSn and LC-HR-MS/MS". Drug Testing and Analysis. 6 (10): 1038–48. doi:10.1002/dta.1621. PMID 24591097.
^ Wink CS, Meyer GM, Meyer MR, Maurer HH (November 2015). "Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs-Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps". Toxicology Letters. 238 (3): 39–44. doi:10.1016/j.toxlet.2015.08.012. PMID 26276083.
^ Beharry S, Gibbons S (October 2016). "An overview of emerging and new psychoactive substances in the United Kingdom" (PDF). Forensic Science International. 267: 25–34. doi:10.1016/j.forsciint.2016.08.013. PMID 27552699.
^ Wink CS, Meyer GM, Zapp J, Maurer HH (February 2015). "Lefetamine, a controlled drug and pharmaceutical lead of new designer drugs: synthesis, metabolism, and detectability in urine and human liver preparations using GC-MS, LC-MS(n), and LC-high resolution-MS/MS". Analytical and Bioanalytical Chemistry. 407 (6): 1545–57. doi:10.1007/s00216-014-8414-3. PMID 25577353. S2CID 26014465.
^ "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015.

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[1] Morris H, Wallach J (July–August 2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID 24678061.

[2] Meyer MR, Orschiedt T, Maurer HH (February 2013). "Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein". Toxicology Letters. 217 (2): 137–42. doi:10.1016/j.toxlet.2012.12.012. PMID 23273999.

[Wink_2014-3] Wink CS, Meyer GM, Wissenbach DK, Jacobsen-Bauer A, Meyer MR, Maurer HH (October 2014). "Lefetamine-derived designer drugs N-ethyl-1,2-diphenylethylamine (NEDPA) and N-iso-propyl-1,2-diphenylethylamine (NPDPA): metabolism and detectability in rat urine using GC-MS, LC-MSn and LC-HR-MS/MS". Drug Testing and Analysis. 6 (10): 1038–48. doi:10.1002/dta.1621. PMID 24591097.

[4] Wink CS, Meyer GM, Meyer MR, Maurer HH (November 2015). "Toxicokinetics of lefetamine and derived diphenylethylamine designer drugs-Contribution of human cytochrome P450 isozymes to their main phase I metabolic steps". Toxicology Letters. 238 (3): 39–44. doi:10.1016/j.toxlet.2015.08.012. PMID 26276083.

[pmid27552699-5] Beharry S, Gibbons S (October 2016). "An overview of emerging and new psychoactive substances in the United Kingdom" (PDF). Forensic Science International. 267: 25–34. doi:10.1016/j.forsciint.2016.08.013. PMID 27552699.

[6] Wink CS, Meyer GM, Zapp J, Maurer HH (February 2015). "Lefetamine, a controlled drug and pharmaceutical lead of new designer drugs: synthesis, metabolism, and detectability in urine and human liver preparations using GC-MS, LC-MS(n), and LC-high resolution-MS/MS". Analytical and Bioanalytical Chemistry. 407 (6): 1545–57. doi:10.1007/s00216-014-8414-3. PMID 25577353. S2CID 26014465.

[7] "23 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 1 June 2015.

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Metabolism

Legality

See also

References