Rolicyclidine

Identification

Name
Rolicyclidine
Accession Number
DB01549
Type
Small Molecule
Groups
Experimental, Illicit
Description

Rolicyclidine (PCPy) is a dissociative anesthetic drug with hallucinogenic and sedative 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.

Structure
Thumb
Synonyms
  • 1-(1-phenylcyclohexyl)pyrrolidine
  • PCPy
  • Pyrrolidine analog of phencyclidine
  • Roliciclidina
  • Rolicyclidinum
External IDs
DEA No. 7458
Categories
UNII
183O9O9JE3
CAS number
2201-39-0
Weight
Average: 229.3605
Monoisotopic: 229.183049741
Chemical Formula
C16H23N
InChI Key
FYOWWXMGDATDQY-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(1-phenylcyclohexyl)pyrrolidine
SMILES
C1CCN(C1)C1(CCCCC1)C1=CC=CC=C1

Pharmacology

Indication

Rolicyclidine has anesthetic properties and can induce a sedative effect.

Structured Indications
Not Available
Pharmacodynamics

Rolicyclidine is similar in effects to phencyclidine but is slightly less potent and has less stimulant effects. Instead it acts by inducing a sedative effect described as being somewhat similar to a barbiturate, but with additional PCP-like dissociative, anaesthetic and hallucinogenic effects.

Mechanism of action

Rolicyclidine works primarily as an NMDA receptor antagonist, which blocks the activity of the NMDA Receptor.

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3ANot AvailableHuman
UD(2) dopamine receptorNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
62436
PubChem Substance
46507433
ChemSpider
56218
ChEBI
60805
ChEMBL
CHEMBL1719398
Wikipedia
Rolicyclidine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0239 mg/mLALOGPS
logP4.54ALOGPS
logP4.04ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)10.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.05 m3·mol-1ChemAxon
Polarizability27.69 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9972
Blood Brain Barrier+0.9934
Caco-2 permeable+0.8046
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.7688
P-glycoprotein inhibitor IINon-inhibitor0.5156
Renal organic cation transporterInhibitor0.7688
CYP450 2C9 substrateNon-substrate0.7933
CYP450 2D6 substrateNon-substrate0.8981
CYP450 3A4 substrateNon-substrate0.5381
CYP450 1A2 substrateInhibitor0.5635
CYP450 2C9 inhibitorNon-inhibitor0.9091
CYP450 2D6 inhibitorInhibitor0.9172
CYP450 2C19 inhibitorNon-inhibitor0.5905
CYP450 3A4 inhibitorNon-inhibitor0.8459
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8619
Ames testNon AMES toxic0.8221
CarcinogenicityNon-carcinogens0.9
BiodegradationNot ready biodegradable0.9638
Rat acute toxicity3.3265 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8025
hERG inhibition (predictor II)Inhibitor0.6536
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Cyclohexylamines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aralkylamine / Cyclohexylamine / Benzenoid / N-alkylpyrrolidine / Monocyclic benzene moiety / Pyrrolidine / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organoheterocyclic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amine, pyrrolidines (CHEBI:60805)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone . [PubMed:20641908]
  2. Yuede CM, Wozniak DF, Creeley CE, Taylor GT, Olney JW, Farber NB: Behavioral consequences of NMDA antagonist-induced neuroapoptosis in the infant mouse brain. PLoS One. 2010 Jun 29;5(6):e11374. doi: 10.1371/journal.pone.0011374. [PubMed:20613880]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Seeman P, Guan HC, Hirbec H: Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009 Aug;63(8):698-704. doi: 10.1002/syn.20647. [PubMed:19391150]

Drug created on July 31, 2007 07:10 / Updated on December 01, 2017 14:45