Rolicyclidine

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Rolicyclidine
Rolicyclidine.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1-phenylcyclohexyl)pyrrolidine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H23N
Molar mass 229.367 g·mol−1
3D model (JSmol)
  • c1ccccc1C3(N2CCCC2)CCCCC3
  • InChI=1S/C16H23N/c1-3-9-15(10-4-1)16(11-5-2-6-12-16)17-13-7-8-14-17/h1,3-4,9-10H,2,5-8,11-14H2 Yes check.svgY
  • Key:FYOWWXMGDATDQY-UHFFFAOYSA-N Yes check.svgY
   (verify)

Rolicyclidine (PCPy) is a dissociative anesthetic that is similar in effects to phencyclidine, but is slightly less potent and has fewer stimulant effects. [1] It instead produces a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects. [2] 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.

See also

Related Research Articles

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<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 hallucinogenic drug used for its 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.

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<span class="mw-page-title-main">NMDA receptor antagonist</span> Class of anesthetics

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

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<span class="mw-page-title-main">2-MDP</span> Chemical compound

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

Dexoxadrol (Dioxadrol) is a dissociative anaesthetic drug which has been found to be an NMDA antagonist and produces similar effects to PCP in animals. Dexoxadrol, along with another related drug etoxadrol, were developed as analgesics for use in humans, but development was discontinued after patients reported side effects such as nightmares and hallucinations.

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

Etoxadrol (CL-1848C) is a dissociative anaesthetic drug that has been found to be an NMDA antagonist and produce similar effects to PCP in animals. Etoxadrol, along with another related drug dexoxadrol, were developed as analgesics for use in humans, but development was discontinued in the late 1970s after patients reported side effects such as nightmares and hallucinations.

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<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">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-MeO-PCMo</span> Chemical compound

3-MeO-PCMo is a dissociative anesthetic drug which is similar in structure to phencyclidine and been sold online as a designer drug. The inhibitory effect of 3-MeO-PCMo on the reduction in the density of the drebrin clusters by NMDAR stimulation with glutamic acid is lower than that of PCP or 3-MeO-PCP, with half maximal inhibitory concentration (IC50) values of 26.67 μM (3-MeO-PCMo), 2.02 μM (PCP) and 1.51 μM (3-MeO-PCP).

<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.

<span class="mw-page-title-main">3-Methyl-PCP</span>

3-Methyl-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. It was first synthesised in the 1960s, but was only identified on the illicit market in Hungary in September 2020, and was made illegal in Hungary in April 2021.

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

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>

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. Kalir A, Edery H, Pelah Z, Balderman D, Porath G (May 1969). "1-Phenycycloalkylamine derivatives. II. Synthesis and pharmacological activity". Journal of Medicinal Chemistry. 12 (3): 473–7. doi:10.1021/jm00303a030. PMID   4977945.
  2. DEA Microgram Bulletin, 8, 143, 1975