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Identification
NameRolicyclidine
Accession NumberDB01549
TypeSmall Molecule
GroupsExperimental, Illicit
DescriptionRolicyclidine (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 Identifiers
  • DEA No. 7458
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII183O9O9JE3
CAS number2201-39-0
WeightAverage: 229.3605
Monoisotopic: 229.183049741
Chemical FormulaC16H23N
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Cyclohexylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Monocyclic benzene moiety
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationRolicyclidine has anesthetic properties and can induce a sedative effect.
PharmacodynamicsRolicyclidine 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 actionRolicyclidine works primarily as an NMDA receptor antagonist, which blocks the activity of the NMDA Receptor.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism (By similarity).
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular Weight:
125464.07 Da
References
  1. Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone . 2004;():. [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
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 ]
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Drug created on July 31, 2007 07:10 / Updated on August 17, 2016 12:23