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Identification
NameRolicyclidine
Accession NumberDB01549
Typesmall molecule
Groupsexperimental, 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
SynonymLanguageCode
1-(1-phenylcyclohexyl)pyrrolidineNot AvailableNot Available
PCPyNot AvailableNot Available
Pyrrolidine analog of phencyclidineNot AvailableNot Available
RoliciclidinaSpanishINN
RolicyclidinumLatinINN
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsPyrrolidines; Tertiary Amines; Polyamines
Substituentspyrrolidine; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9972
Blood Brain Barrier + 0.9934
Caco-2 permeable + 0.8046
P-glycoprotein substrate Substrate 0.5
P-glycoprotein inhibitor I Non-inhibitor 0.7688
P-glycoprotein inhibitor II Non-inhibitor 0.5156
Renal organic cation transporter Inhibitor 0.7688
CYP450 2C9 substrate Non-substrate 0.7933
CYP450 2D6 substrate Non-substrate 0.8981
CYP450 3A4 substrate Non-substrate 0.5381
CYP450 1A2 substrate Inhibitor 0.5635
CYP450 2C9 substrate Non-inhibitor 0.9091
CYP450 2D6 substrate Inhibitor 0.9172
CYP450 2C19 substrate Non-inhibitor 0.5905
CYP450 3A4 substrate Non-inhibitor 0.8459
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8619
Ames test Non AMES toxic 0.8221
Carcinogenicity Non-carcinogens 0.9
Biodegradation Not ready biodegradable 0.9638
Rat acute toxicity 3.3265 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8025
hERG inhibition (predictor II) Inhibitor 0.6536
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.39e-02 g/lALOGPS
logP4.54ALOGPS
logP4.04ChemAxon
logS-4ALOGPS
pKa (strongest basic)10.78ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area3.24ChemAxon
rotatable bond count2ChemAxon
refractivity73.05ChemAxon
polarizability27.69ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound62436
PubChem Substance46507433
ChemSpider56218
ChEBI60805
ChEMBL
WikipediaRolicyclidine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

References:

  1. Leung K: 4-Acetoxy-7-chloro-3-(3-(-4-[11C]methoxybenzyl)phenyl)-2(1H)-quinolone Pubmed
  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. Pubmed

2. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

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. Pubmed

Comments
Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15