NPDPA

Last updated
NPDPA
Isopropylphenidine.svg
Legal status
Legal status
Identifiers
  • N-(propan-2-yl)-1,2-diphenylethylamine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C17H21N
Molar mass 239.362 g·mol−1
3D model (JSmol)
  • c1ccccc1CC(NC(C)C)c2ccccc2
  • 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.

Contents

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.

See also

Related Research Articles

<span class="mw-page-title-main">5-MeO-DALT</span> Chemical compound

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">Phthalimidopropiophenone</span> Chemical compound

Phthalimidopropiophenone is a chemical intermediate used in the synthesis of cathinone. It has been found to be sold on the illicit market as a controlled substance analogue, but little is currently known about its pharmacology or toxicology.

<span class="mw-page-title-main">Dimethocaine</span> Stimulant

Dimethocaine, also known as DMC or larocaine, is a compound with a stimulatory effect. This effect resembles that of cocaine, although dimethocaine appears to be less potent. Just like cocaine, dimethocaine is addictive due to its stimulation of the reward pathway in the brain. However, dimethocaine is a legal cocaine replacement in some countries and is even listed by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) under the category “synthetic cocaine derivatives”. The structure of dimethocaine, being a 4-aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature.

<span class="mw-page-title-main">JWH-018</span> Chemical compound

JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in animals similar to those of tetrahydrocannabinol (THC), a cannabinoid naturally present in cannabis, leading to its use in synthetic cannabis products that in some countries are sold legally as "incense blends".

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<span class="mw-page-title-main">3',4'-Methylenedioxy-α-pyrrolidinobutiophenone</span> Stimulant drug

3',4'-Methylenedioxy-α-pyrrolidinobutyrophenone (MDPBP) is a stimulant of the cathinone class developed in the 1960s, which has been reported as a novel designer drug. MDPBP is sometimes sold under the name "NRG-1" as a mixture with other cathinone derivatives, including flephedrone, pentylone, MαPPP and its higher homologue MDPV. As with other cathinones, MDPBP has been shown to have reinforcing effects in rats.

<span class="mw-page-title-main">DALT</span> Chemical compound

N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance. It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine.

<span class="mw-page-title-main">Methiopropamine</span> Structural analog of methamphetamine

Methiopropamine (MPA) is an organic compound structurally related to methamphetamine. Originally reported in 1942, the molecule consists of a thiophene group with an alkyl amine substituent at the 2-position. It appeared for public sale in the UK in December 2010 as a "research chemical" or "legal high", recently branded as Blow. It has limited popularity as a recreational stimulant.

<span class="mw-page-title-main">4-Methylethcathinone</span> Stimulant designer drug

4-Methylethcathinone or 4-MEC is a chemical that bears a chemical resemblance to mephedrone. Due to its similarity to mephedrone, it is thought to be a stimulant and entactogen drug of the phenethylamine, amphetamine, and cathinone chemical classes. It has been marketed alone or in mixtures with other substituted cathinones under the name "NRG-2", although other blends such as "NRG-1" may have been more ambiguous with their ingredients.

<span class="mw-page-title-main">5-MAPB</span> Chemical compound

5-MAPB is an entactogenic designer drug similar to MDMA in its structure and effects.

<span class="mw-page-title-main">6-MAPB</span> Chemical compound

6-MAPB is a psychedelic and entactogenic drug which is structurally related to 6-APB and MDMA. It is not known to have been widely sold as a "designer drug" but has been detected in analytical samples taken from individuals hospitalised after using drug combinations that included other benzofuran derivatives. 6-MAPB was banned in the UK in June 2013, along with 9 other related compounds which were thought to produce similar effects.

<span class="mw-page-title-main">Diphenidine</span> Dissociative anesthetic designer drug

Diphenidine is a dissociative anesthetic that has been sold as a designer drug. The synthesis of diphenidine was first reported in 1924, and employed a Bruylants reaction analogous to the one that would later be used to discover phencyclidine in 1956. Shortly after the 2013 UK ban on arylcyclohexylamines, diphenidine and the related compound methoxphenidine became available on the grey market. Anecdotal reports describe high doses of diphenidine producing "bizarre somatosensory phenomena and transient anterograde amnesia." Diphenidine and related diarylethylamines have been studied in vitro as treatments for neurotoxic injury and are antagonists of the NMDA receptor. In dogs diphenidine exhibits greater antitussive potency than codeine phosphate.

<span class="mw-page-title-main">Methoxphenidine</span> Chemical compound

Methoxphenidine is a dissociative of the diarylethylamine class that has been sold online as a designer drug. Methoxphenidine was first reported in a 1989 patent where it was tested as a treatment for neurotoxic injury. Shortly after the 2013 UK ban on arylcyclohexylamines methoxphenidine and the related compound diphenidine became available on the gray market, where it has been encountered as a powder and in tablet form. Though diphenidine possesses higher affinity for the NMDA receptor, anecdotal reports suggest methoxphenidine has greater oral potency. Of the three isomeric anisyl-substituents methoxphenidine has affinity for the NMDA receptor that is higher than 4-MeO-Diphenidine but lower than 3-MeO-Diphenidine, a structure–activity relationship shared by the arylcyclohexylamines.

<span class="mw-page-title-main">3-Fluorophenmetrazine</span> Stimulant designer drug

3-Fluorophenmetrazine is a phenylmorpholine-based stimulant and fluorinated analogue of phenmetrazine that has been sold online as a designer drug.

<span class="mw-page-title-main">Ephenidine</span> Dissociative anesthetic designer drug

Ephenidine is a dissociative anesthetic that has been sold online as a designer drug. It is illegal in some countries as a structural isomer of the banned opioid drug lefetamine, but has been sold in countries where it is not yet banned.

<span class="mw-page-title-main">MDMB-CHMICA</span> Chemical compound

MDMB-CHMICA is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug. While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this code name (i.e. the isopropyl instead of t-butyl analogue of MDMB-CHMINACA) has been identified on the designer drug market in 2015 as AMB-CHMINACA.

<span class="mw-page-title-main">Nifoxipam</span> Benzodiazepine designer drug

Nifoxipam is a benzodiazepine that is a minor metabolite of flunitrazepam and has been sold online as a designer drug.

<span class="mw-page-title-main">Methoxypiperamide</span> Chemical compound

Methoxypiperamide is a psychoactive drug of the piperazine class that has been sold online as a designer drug. It is the 4-methoxy-α-keto analog of methylbenzylpiperazine.

<span class="mw-page-title-main">4-EA-NBOMe</span> Substituted amphetamine designer drug

4-EA-NBOMe is a substituted amphetamine and 25-NB derivative which has been sold as a designer drug. It was first identified by a forensic laboratory in Germany in 2014, but while its analytical properties and metabolism have been studied, its pharmacology remains unknown.

4-Ethylamphetamine (4-EA) is a substituted amphetamine derivative which has been sold as a designer drug. It is mainly known as a synthetic intermediate used as a building block to manufacture larger molecules, but 4-EA is closely related in chemical structure to designer drugs such as 4-methylamphetamine and 4-ethylmethcathinone, and is both a synthetic precursor and a metabolite of the 25-NB derivative 4-EA-NBOMe.

References

  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.
  3. 1 2 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.
  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.