3-Methyl-PCP

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3'-Me-PCP
3'-Me-PCP.svg
Legal status
Legal status
Identifiers
  • 1-[1-(3-methylphenyl)cyclohexyl]piperidine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C18H27N
Molar mass 257.421 g·mol−1
3D model (JSmol)
  • CC1=CC(=CC=C1)C2(CCCCC2)N3CCCCC3
  • InChI=1S/C18H27N/c1-16-9-8-10-17(15-16)18(11-4-2-5-12-18)19-13-6-3-7-14-19/h8-10,15H,2-7,11-14H2,1H3
  • Key:BMFKUCGCXMDGBK-UHFFFAOYSA-N

3-Methyl-PCP (3'-Methyl-PCP, meta-Methyl-PCP, 3-Me-PCP) is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as 3'-MeO-PCP and 3'-Me-PCPy. [1] [2] It was first synthesised in the 1960s, [3] but was only identified on the illicit market in Hungary in September 2020, [4] and was made illegal in Hungary in April 2021. [5]

See also

Related Research Articles

<span class="mw-page-title-main">Phencyclidine</span> Dissociative hallucinogenic drug, mostly used recreationally

Phencyclidine or phenylcyclohexyl piperidine (PCP), also known as angel dust among other names, is a dissociative anesthetic mainly used recreationally for its significant mind-altering effects. PCP may cause hallucinations, distorted perceptions of sounds, and violent behavior. As a recreational drug, it is typically smoked, but may be taken by mouth, snorted, or injected. It may also be mixed with cannabis or tobacco.

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

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, and typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

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

Rolicyclidine (PCPy) is a dissociative anesthetic that is similar in effects to phencyclidine, but is slightly less potent and has fewer stimulant effects. It instead produces a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects. Due to its similarity in effects to PCP, PCPy was placed into the Schedule I list of illegal drugs in the 1970s, although it has never been widely abused and is now little known.

<span class="mw-page-title-main">Eticyclidine</span> Medication

Eticyclidine is a dissociative anesthetic drug with hallucinogenic effects. It is similar in effects to phencyclidine but is slightly more potent. PCE was developed by Parke-Davis in the 1970s and evaluated for anesthetic potential under the code name CI-400, but research into PCE was not continued after the development of ketamine, a similar drug with more favourable properties. PCE is slightly more potent than PCP and has similar effects, but its unpleasant taste and tendency to cause nausea made it less accepted by users. Due to its similarity in effects to PCP, PCE was placed into the Schedule 1 list of illegal drugs in the 1970s, although it was only briefly abused in the 1970s and 1980s and is now little known.

Gacyclidine is a psychoactive drug which acts as a dissociative via functioning as a non-competitive NMDA receptor antagonist. It is closely related to phencyclidine (PCP), and specifically, is a derivative of tenocyclidine (TCP).

<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-MeO-PCP</span> Chemical compound

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter. The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.

<span class="mw-page-title-main">4-MeO-PCP</span> Chemical compound

4-Methoxyphencyclidine is a dissociative anesthetic drug that has been sold online as a research chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by the Parke-Davis medicinal chemist Victor Maddox. A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP. 4-MeO-PCP was the first arylcyclohexylamine research chemical to be sold online, it was introduced in late 2008 by a company trading under the name CBAY and was followed by several related compounds such as 3-MeO-PCP and methoxetamine. 4-MeO-PCP has lower affinity for the NMDA receptor than PCP, but higher affinity than ketamine, it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects. Users have reported substantial differences in active dose, these discrepancies can be partially explained by the presence of unreacted PCC and other impurities in samples sold on the grey market. 4-MeO-PCP has Ki values of 404 nM for the NMDA receptor, 713 nM for the norepinephrine transporter, 844 nM for the serotonin transporter, 296 nM for the σ1 receptor and 143 nM for the σ2 receptor.

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

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, and has reportedly been sold as a designer drug in Germany and other European countries since the late 1990s.

<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-MeO-PCE</span> Chemical compound

3-Methoxyeticyclidine (3-MeO-PCE), also known as methoxieticyclidine, is a dissociative anesthetic that is qualitatively similar to PCE and PCP and has been sold online as a designer drug.

<span class="mw-page-title-main">3-HO-PCP</span> Chemical compound

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.

<i>N</i>-Ethylhexedrone Chemical compound

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

<span class="mw-page-title-main">3-Methyl-PCPy</span> Chemical compound

3-Methyl-PCPy (3-Me-PCPy) is an arylcyclohexylamine derivative with an unusual spectrum of pharmacological effects, acting as both a potent NMDA antagonist and also a triple reuptake inhibitor which inhibits reuptake of all three monoamine neurotransmitters serotonin, dopamine and noradrenaline. It also acts as a high affinity sigma receptor ligand, selective for the σ2 subtype. It produces both stimulant and dissociative effects in animal behavioural studies.

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

MXiPr is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as ketamine and methoxetamine. It was first identified in Slovenia in December 2020, and was made illegal in Hungary in April 2021.

<span class="mw-page-title-main">3-Chloro-PCP</span> Chemical compound

3-Chloro-PCP (3'-Cl-PCP) is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It has comparable potency to phencyclidine but with a slightly different effects profile, being somewhat more potent as an NMDA antagonist but around the same potency as a dopamine reuptake inhibitor. It was first identified in Slovenia in December 2020, and was made illegal in Hungary in April 2021.

<span class="mw-page-title-main">3-Fluoro-PCP</span> Chemical compound

3-Fluoro-PCP is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It was first identified in Slovenia in October 2020, and was made illegal in Hungary in April 2021.

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

Deoxymethoxetamine is a recreational designer drug from the arylcyclohexylamine family, with dissociative effects. It is an analogue of methoxetamine where the 3-methoxy group has been replaced by methyl. It has been sold online since around October 2020, and was first definitively identified by a forensic laboratory in Denmark in February 2021.

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

Methylenedioxyphencyclidine is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, with similar effects to related drugs such as 3-MeO-PCP and 4-MeO-PCP.

References

  1. Linders J, Furlano DC, Mattson MV, Jacobson AE, Rice KC (February 2010). "Synthesis and preliminary biochemical evaluation of novel derivatives of PCP". Letters in Drug Design & Discovery. 7 (2): 79–87. doi:10.2174/157018010790225813.
  2. Wallach J, De Paoli G, Adejare A, Brandt SD (2014). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–50. doi:10.1002/dta.1468. PMID   23554350.
  3. 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.
  4. Jankovic M (28 January 2021). "EU Early Warning System" (PDF). Der Koordinator für Psychiatrie, Sucht- und Drogenfragen und der Beauftragte für Sucht- und Drogenfragen der Stadt Wien.
  5. Minister for Human Capacities. "Amendment of Minister for Human Capacities Decree No 55/2014 of 30 December 2014 on substances or groups of compounds classified as new psychoactive substances, 2021/225/HU". European Commission.